“Ms. Jackson”— Outkast

Why would the best ever want to stop being the best? Rob tries to figure this out in this week's episode covering Outkast. He proves that Big Boi and André 3000 will always be better together by comparing the tag team effort in their hit song, “Ms. Jackson,” and their split album ‘Speakerboxxx/The Love Below’. Later, he is joined by ‘Last Song Standing’ hosts, Cole Cuchna and Charles Holmes, to discuss how Outkast has aged for newer rap listeners and to share their favorite Outkast album in their self-proclaimed old age. Host: Rob Harvilla Guests: Charles Holmes and Cole Cuchna Producers: Olivia Crerie, Chris Sutton, and Justin Sayles Learn more about your ad choices. Visit podcastchoices.com/adchoices

• 0:00Speaker 00

  Hey, it's Craig Horlbeck here to tell you that the NFL is back, whether you like it or not, and we are covering all the latest news, trades, rankings, and more on The Ringer Fantasy Football Show with my two co-hosts, who are both named Danny. Check The Ringer Fantasy Football Show out on Spotify or on our new YouTube channel.

• 0:18Speaker 01

  This episode is brought to you by The Home Depot. The Home Depot has everything you need to launch your holiday season in style. Upgrade your yard with this year's hottest holiday decor, including the show-stopping towering Santa—oh, I like that one—and his impressive reindeer, both 8.5 feet and both designed with incredible detail that stands out day or night. When you want decor that delivers impact, The Home Depot has it. Make your home Santa's favorite stop with the holiday decor you want, all waiting for you at The Home Depot. This episode is brought to you by Boar's Head. You know what I love about football season? It's the football, but also the football-watching food. And nothing hits like a Boar's Head sandwich when I'm watching a game. Really, any game-day sandwich better with Boar's Head. Philly cheesesteak, layer-up buttery slider rolls with Boar's Head London Broil

• 1:02Speaker 01

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• 1:36Speaker 02

  I hung up his poster on my bedroom wall, and I left it there all through high school, all through the '90s. A long rectangular poster of him, six feet taller so, hung between my two bedroom windows on this narrow stretch of wall, angled slightly outward, so he sort of leaned, he sort of loomed over me. And even more importantly, he loomed over my stereo. My stereo, the classic '90s triple combo, right? Single CD player on top, radio tuner in the middle, dual tape deck on the bottom. My stereo sat on an upside-down milk crate on the floor, right beneath his poster.

• 2:22Speaker 02

  Look, just so you understand the grave importance of this. This is my teenage bedroom, and my teenage bedroom is where I keep my stereo and my CD collection. And my stereo and CD collection are my whole reason for existence, my whole personality, my whole universe. My raison d'etre, as the French say. However the French pronounce that, I got no idea. I took Spanish. My stereo is my most prized possession. It is a legitimately sacred object. If my house is ever on fire, then my stereo will pick me up and carry me out of the house. And thus, there is a legitimately shrine-like aspect to this arrangement.

• 3:05Speaker 02

  The celestial light pouring through my two-bedroom windows with my beloved stereo perched royally on the milk crate between them, and his poster looming high above it. He confers additional greatness onto my stereo, and my stereo confers additional greatness onto him. These details interest me. This giant poster of him that hung on my bedroom wall all through high school interests me. The fact that I had no other posters, only him, this interests me. His shameless commodification interests me. His wanton global deification interests me.

• 3:48Speaker 02

  His undeniable and distinctly tyrannical greatness interests me. Another thing that interests me about him is that I fucking hated him.

• 4:14Speaker 02

  And I took that personally on May 7th, 1989. Michael Jordan hit a buzzer beater in the deciding game five of the first round NBA Eastern Conference Playoff series between his detestable Chicago Bulls and my beloved, valorous, doomed Cleveland Cavaliers. This is the shot officially known in eternal NBA lore as "The Shot." Jordan over Craig Elo, right at the free throw line. Replaying that clip just now and listening to the announcer, I was like, gets the ball from Hugh Evans? The Bulls had a guy named Hugh Evans? No, Hugh Evans was the referee who handed the ball to Brad Sellers with three seconds

• 4:57Speaker 02

  on the clock and Brad Sellers inbounded it to Jordan who hit the shot. So, you know, fuck Brad Sellers. Also, the shot rattles in, the game's over, Elo collapses on the sideline and Jordan does his stupid iconic triple fist pump as 11-year-old me screams various obscenities at my television. Why is Michael Jordan's poster on my wall? I am a devout Cleveland Cavs fan. My teenage bedroom, where I keep my beloved stereo and CD collection, is located in my house in suburban Cleveland. Michael Jordan is my sworn enemy.

• 5:39Speaker 02

  Michael Jordan is the bane of my stereo-based existence. I cannot frickin' believe I just voluntarily played you audio of "The Shot." My parents are going to disown me. I am disgusted with myself. Yo, pardon me for 10 seconds while I restore balance to the force.

• 6:12Speaker 02

  On June 16th, 2016, LeBron James executed a breathtaking late fourth quarter full-court chase-down block of Andre Iguodala's feeble-ass attempt at a go-ahead layup, setting the stage for my beloved, valorous, victorious Cleveland Cavaliers to defeat the detestable Golden State Warriors in the deciding Game 7 of the NBA Finals. A block forever known in NBA lore as "The Block." So suck it. The Cavs won the title. The Warriors blew a 3-1 lead. Excuse me, why is Michael Jordan's poster on my wall in my suburban Cleveland bedroom

• 6:56Speaker 02

  all throughout the 90s when he killed the Cavs every year? Back when I still played Yahoo Fantasy Basketball, I preferred team names that were puns on the names of late 80s Cavs players. So what, Mark Price is right? I did that one. L. Ron Harper? Hell yeah. Hot Rod Williamsburg? Absolutely. Leisure Suit Larry Nance? No, that's dumb. Brad Doherty? He was our center and it took me forever to think up a name for him, but finally I nailed it. Friends of Doherty? Oh, well. Excuse me, why is Michael Jordan's poster on my wall right above my beloved stereo if I hate him so much? Because he was the best.

• 7:43Speaker 03

  17 seconds. 17 seconds from Game 7 or from championship number 6. Jordan, open. Chicago with the lead.

• 7:58Speaker 02

  On June 14th, 1998, Michael Jordan hit a game-winning jumper in the closing seconds of the concluding Game 6 of the NBA Finals, vanquishing the Utah Jazz and giving Jordan and the whole Chicago Bulls, but really it was just Jordan, his sixth and blessedly final championship. I watched this live and I was absolutely rooting against him. He pushed off. I rooted against him even when he wasn't demolishing my team specifically. I vehemently rooted against Jordan because he was the best and I reverently hung a poster of Jordan dunking on some dude from the Clippers, I think, on my wall because he was the best.

• 8:40Speaker 02

  Because when you are the best, you inspire that singular deadly mixture of anger and awe, abject frustration and total adulation. Everyone watches you and wants to see you fail, even if they not so secretly realize that of course you won't fail because you're the best, even if you did push off. And then, sometimes, when you've been the best at something for so long that you get restless and bored and dissatisfied, maybe you shock the world by quitting the thing that you're the best at so you can go not be the best at some other thing.

• 9:32Speaker 02

  Amazing call by Harry Carey here. First of all, the deified Chicago announcer and institution, Harry Carey, R.I.P. Harry manages to make this call while there are apparently 12 full bratwursts crammed into his mouth, including the buns. A truly disconcerting saliva situation transpiring within Harry Carey at this exact moment. Harry Carey was the best also, obviously.

• 10:03Speaker 04

  Michael Jordan has tied up the ballgame with a ground double to left. And this crowd has seen what it came here for.

• 10:14Speaker 02

  On April 7th, 1994, during a heated showdown between his own Chicago White Sox and their crosstown rivals, the Chicago Cubs, Michael Jordan hit an electrifying game-tying double that ultimately, this is an exhibition game, it doesn't matter, it's not a real game. In 1993, three-time NBA champion Michael Jordan shocked the world by quitting basketball so he could go try to play pro baseball for the Chicago White Sox instead. And he mostly sucked. I was gonna play you clips of Michael Jordan striking out, actually, just so I could go, "Ha ha, you suck, boo." But these clips are harder to find on the internet. Jordan

• 10:57Speaker 02

  never actually made it to the pros, just the minors. He played for the White Sox Double-A Team, the Birmingham Barons. Let's see here, one season, 436 at-bats, 202 average, that sucks, three home runs, whatever, 30 steals, that's good, 18 times caught stealing, that's funny, and oof, 11 outfield errors, tied for the league lead. One time, somebody hit a long fly ball to Michael Jordan and he totally biffed it, and the ball bounced off his head and over the fence for a homerun. That wasn't him, obviously. That happened

• 11:38Speaker 02

  to Jose Canseco, but that's still one of the funniest things I've ever seen, so. And then, after that one season, Jordan quit baseball and went back to basketball. He went back to the Bulls and won three more NBA championships, including that last one where he pushed off. But what a strange interlude that was. Michael Jordan refusing to do the thing he was the best at, because he'd rather go to Alabama and strike out and get caught stealing and take routine fly balls off the dome, that wasn't him, instead. What a surreal, what an almost offensive sight. Is that not a direct affront? Is that not

• 12:17Speaker 02

  an insult to those of us who are not the best at something? Why would you ever do that? Why would you ever not do the thing you were the best at? Well...

• 12:31Speaker 02

  Maybe you just really like playing the flute.

• 12:55Speaker 02

  This is a song from 2023. This song is 12 minutes and 20 seconds long. And with no further context whatsoever, there's already plenty to talk about, like musically. Yes? The unhurried elegance of this flute riff that starts out alternative and staccato.

• 13:17Speaker 02

  But the riff gathers force. It gathers confidence. It gathers elegance as it goes. The melody smooths out and it peaks right when that cymbal crashes. In that climactic moment there.

• 13:35Speaker 02

  There's something so arresting, so patient, so serene about it. Maybe you listen to music like this all the time and you get really salty about what people call it. New age ambience, spiritual jazz, psychedelic wallpaper, spa core. Or maybe you never listen to music like this by choice and you're only listening to this song because of the guy playing the flute is Andre 3000.

• 14:19Speaker 02

  Everyone calls this a flute album, but Andre 3000 doesn't like that very much. There's a lot more happening here. A lot of other instruments for starters. The cymbals guy, for example, is really feeling it. And yeah, so if by chance you didn't know that was super famous rapper Andre 3000 playing the flute there, did you just now hear that same song, that same riff, that same woodwind action completely differently now that you know it's super famous rapper Andre 3000?

• 14:51Speaker 02

  Did you instantly project all your Andre 3000 context, all your knowledge, all your baggage, all your love, all your personal projections, all your expectations onto this lovely and serene and hypnotic and unhurried song? Of course, that's Andre 3000, AKA Andre Benjamin, AKA Half of OutKast, the beloved Atlanta rap duo, also including Antoine Patton, AKA Big Boi. OutKast, who sold 25 million records, but haven't put out an album since 2006. And they did a semi-grudging 2014 reunion tour of like 700 festivals. And I'm super pissed I missed that, but that probably ain't ever gonna happen again.

• 15:35Speaker 02

  OutKast, not such a serene melody anymore, is it? And Andre can sense your baggage, your projections, your expectations, by the way, which is why this song is called, "I swear, I really wanted to make a scare quotes rap album, but this is literally the way the wind blew me this time." That's the full title. This song charted on the pop charts, on the Billboard Hot 100. It charted at number 90, but still, Andre 3000's long-awaited debut solo album came out in November 2023. It is called "New Blue Sun."

• 16:16Speaker 02

  There is zero rapping. There is maximum flute. It all sounds like that. And all the song titles are like that. Here's a song called, "That night in Hawaii, when I turned into a panther and started making these low-register purring tones that I couldn't control..." dot, dot, dot. Shit was wild.

• 16:56Speaker 02

  Ooh, ominous, sinuous, not un-Panther-like. I dig it, man. I have to say that this song, 10 minutes and 29 seconds long this time, this song really does sound like that night in Hawaii when I turned into a Panther and started making these low register purring tones that I couldn't control. Dot, dot, dot, shit was wild. Just to repeat that song title, in the word shit, instead of an I, it's the symbol for Japanese yen, the capital Y with the two lines through it. Just to clarify, I put on this record, New Blue Sun, in my office a little while ago, and it was such a peaceful scene, drowsy mid-afternoon light leaking through my broken window shades. I'm sipping iced coffee.

• 17:41Speaker 02

  One of my cats is chewing on a cardboard box in the corner. And I'm sitting there trying to write this dumb thing that I'm reading to you right now, and I'm super vibing to this song. And I'm like, that's a really interesting faint percussive crunching sound in the background there. What is that? It was my cat chewing on the box. My cat really mind melded with Andre 3000 for a couple of minutes there. I'm serious. I don't mean that ugly. I'm just telling you what happened. He knows. Andre 3000 knows you want him to rap more, to rap often, to rap always, to rap forever. He knows you want him to make a scare quote rap album.

• 18:23Speaker 02

  He knows you want him to make 30 scare quotes rap albums. I suppose I'm assuming here that you want that, but if you don't want that, why don't you want that? Who doesn't want an Andre 3000 rap album? He doesn't. That's who.

• 18:56Speaker 02

  That's about as agitated, as unsirene as Andre 3000, the woodwind player, is gonna sound. Uh, this is the last song on this New Blue Sun record, and it is called Dreams Once Buried Beneath the Dungeon Floor Slowly Sprout Into Undying Gardens. And even that song title is not a troll, exactly, but it's an echo. It's a wink. It's a nod to the dungeon, the world famous literal basement and makeshift recording studio in East Point in Atlanta, where OutKast first matriculated as part of an esteemed collective of rappers and producers known collectively as the Dungeon Family. I have talked extensively about OutKast before

• 19:41Speaker 02

  in this venue. Uh, I've talked extensively about Andre 3000 before. I've talked about his affection for the dungeon before. I have quoted him saying, uh, in 2001, when OutKast were on the cover of Spin Magazine, Andre 3000 said, quote, "There was a certain feeling there, and I don't have that feeling no more. I want to have that nostalgic feeling of how the dungeons smelled, the way certain beats made you feel. It smelled like dirt, like a mildewy basement when it rains. Crickets." End quote. So it seems like the flute gets Andre 3000 back to that sound, back to that smell, back to the basements. And maybe rapping

• 20:26Speaker 02

  doesn't anymore. Maybe he's a completely different person now. Maybe it's just that he's older. In November 2023, when the New Blue Sun record came out, Andre did a cover story with GQ Magazine. He talked to my old friend, the great GQ writer and celebrity whisperer, Zach Baron. And Andre 3000 gave this great quote that got passed around a lot. Andre said, quote, Even now, people think, "Oh, man, he's just sitting on wraps," or "He's holding these wraps hostage." I ain't got no wraps like that. It actually feels, sometimes it feels inauthentic for me to rap, because I don't have anything to talk about in that way.

• 21:10Speaker 02

  I'm 48 years old. And not to say that age is a thing that dictates what you rap about, but in a way, it does. And things that happen in my life, like, "What are you talking about?" "I got to go get a colonoscopy." "What are you rapping about?" "My eyesight is going bad." You can find cool ways to say it, but, end quote. That line reverberated all around the internet. Andre 3000 doesn't want to rap about his colonoscopy, even when he'd long ago proved that he can rap wonderfully about anything. Even when he can rap like this.

• 22:04Speaker 02

  Because if we're gonna do this, we ought to just do it, right? If we're gonna talk about how Andre 3000 and Big Boi are two of the greatest rappers of all time, we ought to just go straight to B.O.B., "Straight to Bombs Over Baghdad", from the fourth OutKast album, released in 2000 and called "Stankonia." In part, it's the sheer overwhelming unfathomable speed of Bombs Over Baghdad, the breathlessness, the audacity, the breakneck exuberance. But it's not only the pure speed. It's the tremendous personality. It's the unfathomable individual charisma despite the speed.

• 22:42Speaker 02

  Now, look, I genuinely don't care much about the greatest rapper of all time debate. For all my compulsive ranking and list making and hyperbole, I got no dog in that particular fight. E40, maybe, though? And furthermore, whenever some doofus DJ or podcaster or whatever makes a list of the 30 greatest MCs of all time and it goes viral and everyone's pissed about it, I got a blog about it, right? And I don't want to write that blog, okay? I'm like, ah, shit, don't make me think about whether Fabolous is better than Joe Button, you know? He is. But so, is Andre 3000 the best rapper in the definitive, singular, tyrannical Michael Jordan sense?

• 23:27Speaker 02

  Maybe? Yes? Bleh? I don't care, weirdly. But is Andre 3000, the rapper, the best in the figurative, colloquial vibes-based sense? Yes. Obviously, yes, but he doesn't want to rap anymore. He wants to play the flute. He wants to play double A-ball for the Birmingham Barons. I can't say that name. Why can't I say that name? And steal 30 bases and get caught stealing 18 times and hit a few home runs and biff a few fly balls and just generally perpetually do something he's not the best at. And I totally get that. I do.

• 24:10Speaker 02

  But every time I go listen to Bombs Over Baghdad again and rediscover that it's one of my favorite songs of all time, I get a little bummed out that Andre 3000 won't do this anymore. This song is as agitated, as unsirene as Andre 3000 is ever gonna sound rapping. He is working tremendously hard here, but he still sounds phenomenally comfortable. No? My favorite part of his B.O.B. verse is the tie between when he says "cure for cancer, cure for AIDS" and when he rhymes "arm and hammer" with "baby mama." But lucky for you, he does both of those things within 12 seconds.

• 25:03Speaker 02

  I had honestly never fully registered the lines "get back home, things are wrong", well, not really, it was bad all along at the end there. The catastrophic domestic turmoil implied there. I was always having too much fun to notice that part. Y'all don't want to hear him, you just want to dance.

• 25:39Speaker 02

  So today, in part, we have the unenviable task of discussing, of surveying, of lamenting, the dissolution of, not a friendship, but the dissolution of a creative partnership. The slow-motion dissolution of OutKast. The slow-breaking apart of Andre3000 and Big Boi creatively, professionally. We'll deal with that when we have to deal with it. But for the moment, while we're exalting once again in the glory of Bombs Over Baghdad, let's say clearly that Big Boi also is a legitimate best rapper ever candidate. And it's fine if you personally think otherwise, but Big Boi can rap faster than you can think.

• 26:38Speaker 02

  "Big Things Happen Every Time We Meet" is the line that always leaps out at me there. The truth of it, the childlike joy of it. The best part of Big Boi's verse on Bombs Over Baghdad is probably "hold up, slow up, stop, control like Janet Planet, Stan Conia's on ya, movin' like Floyd, coming straight to Florida," that whole part.

• 27:14Speaker 02

  Holy shit. This song was a risk once, theoretically. Uh, this song, upon release in 2000, after OutKast had already released three fantastic and revolutionary all-time classic rap albums, Bombs Over Baghdad was not necessarily what an OutKast fan expected, or wanted, or preferred. Something this frantic, something this blaring, something this, uh, accelerated. What made each successive new classic OutKast song a classic was how eccentric and shocking it often sounded on first contact. Your music isn't truly revolutionary if it doesn't initially start an argument, or really start

• 27:57Speaker 02

  a war. There's another great thing Andre says in that GQ interview. He's talking about how historically his friends often don't like his new music at first, or at all. And he tells a story about playing one of his songs for somebody close to him, and the dude hated it. Andre says, quote, "He said, 'Man, if you put that out, your career is over,' end quote. This was the song."

• 28:36Speaker 02

  Andre's friend hated "Hey Ya." Andre's friend thought "Hey Ya" was career suicide. Andre's friend was incorrect. What part of "Hey Ya" do you think Andre's friend hated specifically? I couldn't even speculate, but I will say it took me a couple of years to make my peace with what Andre rhymes with mama here.

• 29:06Speaker 02

  It's no Arm & Hammer baby mama. That's all I'm saying. Can I tell you a secret? I've been doing this show for five years and counting the 90s. This is my 145th episode, my 145th song, my 145th script. And something just happened to me that has never happened before in all that time. I wrote 90% of this script and then I decided to change the song. I got to talking about another OutKast song and I wrote so much about it that I decided I'd rather do that song instead and I abandoned the original song. Is this an efficient writing method?

• 29:48Speaker 02

  No. Do I want this to ever happen again? No, thank you, but let's embrace the chaos of this happening, hopefully, once. Because my plan this whole time was to do "Hey Ya," but I don't wanna. I got nothing against "Hey Ya," musically or philosophically. I have heard "Hey Ya" a billion times. I suspect everyone has, but that's not "Hey Ya's" fault. It's just, okay, the other song. Okay, I'm about to play this chorus for you. You've heard this chorus a billion times as well, a trillion times possibly even. But just as an experiment, try to listen to this chorus right now

• 30:31Speaker 02

  like you're hearing it for the first time and like you're grappling at first contact with how deliciously bizarre it is. The "oooh," first of all, two "ooohs," actually. There's the immediate bombastic punctuation mark foreground, "oooh." But then in the deep background, there's the drawn out ascending, "oooh," just to ratchet up the tension. There's the, what is that? Is that backwards masking, crackling along the edges? Like this is a cassette tape running in reverse? Is my cat still chewing on that cardboard box? What is the underlying crunching sound transpiring here?

• 31:14Speaker 02

  Plus, the clopping, descending, gloriously piano recital-ass piano line. Do, do, do, do, do, do, do, do, do, do, do. That sounds like it's falling down the stairs. The sheer incongruousness of a massive pop chorus where a superstar rapper so openly and vulnerably apologizes. The palpable wooziness permeating all of this. Partly, it's the keyboards, the piercing haunted house synthesizer line here. But really, there's just an overall vibe, like you tried to download this song from Napster and you somehow only got 65% of it. Yeah, this sounds like a gently corrupted MP3 file.

• 31:59Speaker 02

  This sounds like an exquisitely delicate panic attack. This sounds like a rap song so bizarre, but also so perfect, that the guy singing the hook will soon decide not to even try to write rap songs anymore.

• 32:28Speaker 02

  Yeah, this is the one. My name is Rob Harvilla. This is the 25th episode of 60 Songs That Explained the 90s, Cole and the 2000s. And this week, at the 11th hour, we are discussing Ms. Jackson by OutKast. From their 2000 album, Stankonia. Amidst all this additional turmoil, OutKast hereby join this podcast's hallowed two-episode club. Back in the 90s, we did a whole episode on the OutKast classic, Rosa Parks. Because of course we did. Thus far, the two-episode club also includes Missy Elliott and the Red Hot Chili Peppers. Sure, I'm a little freaked out about the new song thing right now. If you want the truth, give me a second.

• 33:16Speaker 01

  When the sun goes down, the appetizers come out. Yeah, you heard that right. Late night half-priced appetizers are here at Applebee's. Saucy, sweet and spicy boneless wings. Crispy, cheesy mozzarella sticks. Creamy spinach and artichoke dip. Your favorite apps half-priced, available every single night because why should appetizers have curfews? Tap the banner to learn more. Dining only for a limited time at participating locations. Restrictions apply. Copyright 2026 Applebee's Restaurant LLC. This episode is brought to you by NOS Energy. Every ounce of dirt, sweat and gears, every checkered flag and trophy raised, every lap, every race, every hard-fought place. They're all jammed inside every can of NOS Energy.

• 33:59Speaker 01

  High-performance energy for burning the midnight oil in the garage and pedal-to-the-metal human horsepower for the streets. Go ahead, crack open a can of NOS Energy and get after it.

• 34:10Speaker 05

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• 34:42Speaker 02

  Uh, forgive me, but I got another ad for you. Kinda. It's more of a PSA, I suppose. So Andre3000 doesn't want to do it, but another famous, beloved, all-time great rapper did, in fact, rap about getting a colonoscopy. You want to know who? Chuck D.

• 35:03Speaker 06

  If you're 45 and over, listen up tonight. Colon cancer untreated could take your life. Get it right, get screened, no time to be silent. Take a home test or hit your healthcare provider.

• 35:14Speaker 02

  Close enough. In 2021, public enemy luminary and objectively great American Chuck D partnered with the organization's Stand Up to Cancer and Hip Hop Public Health to produce a jovial animated PSA on this very topic. Fairly straightforward. This is an exceptionally worthy cause, especially when you think about the innumerable all-time great rappers we've already lost so young. The earnestness here, the gentle push from a true American hero, goading all of our American heroes to keep themselves as healthy as possible, keep themselves

• 35:54Speaker 02

  alive. Something about the combination of whimsy and gravity in this video is genuinely moving to me. But also, heads up, Chuck D is about to wrap the words, "Go check your colon. Peace. I'm Chuck D."

• 36:11Speaker 06

  I suggest you talk to your family in a circle and screaming and proactive and it won't hurt you. We all want to live our lives the best we could be. Go check your colon. Peace. I'm Chuck D.

• 36:22Speaker 02

  So there you go. It can be done. OutKast formed in Atlanta, Georgia in 1992. Specifically, Andre Benjamin and Antoine Patton met and almost instantly bonded as 16-year-old students at Tri-Cities High School in East Point. Antoine and Andre quickly fell in with a production team called Organized Noise, consisting of Ray Murray, Rico Wade, and my eternal favorite, Sleepy Brown. That's organized noise with a Z in noise. All these dudes record, often, constantly, eternally, in the mythic mildew-smelling cricket-sounding basement of Rico Wade's

• 37:06Speaker 02

  mother's house, aka The Dungeon, home of The Dungeon Family, a burgeoning collective, top-lined, of course, by OutKast, but also including, most notably in this era, the also-quite-stupendous Atlanta rap group Goodie Mob. Sky high, sky high. The first OutKast album, released in 1994, is called Southern Playistic Cadillac Music, and the best song on it is, you guessed it, "Crumble and Herb."

• 37:49Speaker 02

  Look, I gotta speedrun the first three OutKast albums. I gotta limit myself to one song per album, or I'm gonna drive myself nuts. And possibly also drive you nuts. Uh, "Player's Ball" is their first modest hit, and the title track rules. But the best song on Southern playlist at Cadillac Music is "Crumble and Herb." Sleepy Brown sings the chorus, and someone whispers, "It's the master plan." I love it. But so here we have Andre Benjamin, then known simply as Dre. The 3,000 part of his name comes later. Here we have young Dre rapping, "Wetting 'em up like splish, leaving 'em in a splash of blood." And somehow, the nimble playfulness of splish and splash overpowers the tough guy menace

• 38:34Speaker 02

  of the blood part, you know? Same vibe from Big Boi here. There's a majestic ebullience to Big Boi, even when he's ostensibly rapping about drive-bys.

• 39:00Speaker 02

  See, here's an example of how I can drive myself and also possibly drive you crazy, even when I limit myself to one song a piece on the first three OutKast albums. Because I hear Big Boi rap, "Ain't scared of you motherfuckers," and I immediately think of Bernie Mac on Def Comedy Jam in 1992, one of the single greatest stand-up comedy sets of all time. One of the most astounding seven-minute stretches in recorded human history. Big Boi is the best, and Bernie Mac, R.I.P., was most assuredly the best also.

• 39:50Speaker 03

  You don't understand. I ain't scared of you motherfuckers.

• 39:56Speaker 02

  So yeah, that's one song off the first OutKast album, uh, which earns rapturous and yet somewhat tentative industry acclaim, culminating in OutKast winning Best New Rap Group at the 1995 Source Awards, a truly accursed night in hip hop history, wherein, among other unfortunate events, OutKast are booed by some portion of the elitist New York City crowd, and Andre responds with the immortal rallying cry, "The South got something to say." He says "The South got something to say" better than I do, but that's a huge part of what the South's got to say. Okay, the second OutKast album, released in 1996, is called ATLians.

• 40:39Speaker 02

  And for years, I'd screw that up and pronounce that title "Atleans", but I finally trained myself not to do that anymore. Not that I'm bragging. And the surprisingly high-charting pop hit Elevators (Me and You) is a masterpiece. It peaked at number 12 on the Hot 100, which is impressively high for a song that gloriously weird. And the title track rules. But currently, my favorite song on ATLians, see, I nailed it. My favorite song on this record right now is, you guessed it, Mainstream.

• 41:14Speaker 07

  They sworn diving, if they named me good at gin or hopping. Phone call rushing to finish their album, did you find them? Lost dog pedaling, backstroking, what done happened? Deep rhyme to catch of the day, when the recipe called for blackened.

• 41:26Speaker 02

  This song is called "Mainstream", as in floating face down in the mainstream. OutKast are not fully pop stars yet, but they are already grappling with the grave implications of being pop stars. The rude, unreasonable public demands, the compromises, the homogenization, the watering down implied by the very idea of pop stardom. He rhymed the catch of the day when the recipe called for blackened. That's the Andre line that leaps out at me. He is imagining a wayward, aspiring superstar rapper who abandons his southern roots and simply mimics what's on the pop charts and totally biffs it.

• 42:10Speaker 02

  Andre does not want to make scare quotes rap albums if that requires him to chase trends and mimic the catch of the day and sound like everyone else and cater to an unimaginative and possibly predominantly white mainstream audience. And so, just hypothetically, if Dre ever does somehow attract a massive mainstream pop audience, he's gonna do it in the most flamboyant and idiosyncratic way possible. Okay, that went faster. The third OutKast album, released in 1998, is called Equimini, and Rosa Parks, which we discussed at great length last time, is a masterpiece, and so is The Art of Storytelling,

• 42:53Speaker 02

  Part One, and so is Spotty-oty-Dopilicious, and so is Liberation, for that matter. But my single favorite part of Equimini right now is the long fade out on the song Synthesizer.

• 43:22Speaker 02

  Yes, George Clinton just warbled the words, "said she'd lap dance on your laptop while your laptop's in your lap." Go off, George. Synthesizer is a song about how technology is overpowering and usurping and perhaps even destroying humanity. There's a defiantly anti-AI slant to this song if you're willing to be ahistorical and obnoxious about it. But I just love the way the super synthesized beat fades out and the a cappella part starts and a bunch of striking eccentric humans snap their fingers and chant "Synthesizer" for 60 seconds or so. I find that song genuinely moving as well.

• 44:06Speaker 02

  It gives me hope for humanity. It's like a triumphant miniature musical butlerian jihad. Ooh, a Dune reference. Wow, there, we made it through the first three OutKast albums fairly expeditiously.

• 44:23Speaker 02

  I'm proud of us. The fourth OutKast album, released in 2000, is called Stankonia. Is there anything else we need to say about the truly phenomenal era-defining Stankonia single, BOB, Bombs Over Baghdad, which The Ringer once ranked at number one on our giant list of the 50 greatest OutKast songs of all time? No, I think we covered BOB pretty thoroughly. Hmm. No, wait, sorry. Look out! Top five best countdowns in the middle of songs. Here we go. Number five.

• 45:14Speaker 02

  "Centerfold" by the J. Giles Band. I love that part. That part of "Centerfold," a big hit on MTV in 1981. I was three years old, and this song's about having a crush on a pure, innocent girl and then unexpectedly seeing her naked in Playboy or whatever. This is a song concept that I did not fully or even partly grasp at the time, on account of my being three. I love that part of "Centerfold." It makes me want to run through a wall like the Kool-Aid Man, speaking of stuff I loved when I was three. All right. Number four.

• 46:04Speaker 02

  "Countdown" by Beyoncé. Shout out, boys to men. Shout out 2011. Shout out Beyoncé. Remember when Beyoncé said that "Countdown" was the song hipsters love? That's the funniest thing Beyoncé's ever said. It's true, though. All right, back to the 80s. Number three.

• 46:36Speaker 02

  The song is called Major Tom. The singer is named Peter Schilling. Peter Schilling is German, right? Yes, yes, he is. Okay, good. Big hit on MTV in 1982. Major Tom. Ominous and sinuous. Shout out David Bowie. Shout out me. I'm four years old now. All right. You better brace yourselves. Number two.

• 47:12Speaker 02

  Holy moly, Bruce Springsteen's Born to Run. Shout out the year 1975 when I was negative three. Sheesh, is that the hugest, strongest, gnarliest, most electrifying shot of pure adrenaline in rock and roll history? That one, two, three, four, makes me want to pick up the Kool-Aid man and suplex him through a wall. Also, for all you Sopranos fans, here's the funniest thing Christopher Moltisanti ever said.

• 47:47Speaker 08

  Where the fuck you been? You're late. Highway was jammed with broken heroes on a last chance power drive.

• 47:55Speaker 02

  Yeah, that's actually funnier than she must have crawled under there for warmth. Don't worry about it. Oh, thank God. Finally, and the number one best ever countdown in the middle of a song? Yep.

• 48:21Speaker 02

  Unbelievable.

• 48:23Speaker 02

  The bombs over Baghdad mid-song countdown is even huger, stronger, gnarlier, and more electrifying for how sneaky it is, how far down in the mix they bury Andre's "One, two, three, let's go." Stankonia is an exceedingly loud, brash, frantic, chaotic, unrepentantly bonkers album. A genuinely wonderful thing about OutKast overall is that they get way more famous the weirder they get, the more themselves they get. There is no catch of the day imitation, there's no compromise, there is no danger of getting caught floating face down in the mainstream.

• 49:06Speaker 02

  OutKast bend the mainstream to their indomitable will. OutKast compel the mainstream to reverse course and flow back upstream. With Stankonia, OutKast somehow realize their full potential as genre-defining superstar rappers by making what at times sure as hell feels like a nu-metal album.

• 49:40Speaker 02

  Burn, motherfucker, burn, American dreams. You're not truly revolutionary until you've started a revolution. Stankonia is 24 tracks and nearly 75 minutes long. It is the classic rap album equivalent of stuffing 14 bratwursts, including the buns, in your mouth. I am drawn lately to the moments of maximum chaos. How much of this big boy verse can you even reasonably process in real time?

• 50:22Speaker 02

  That's just what's happening. This is Big Boi rapping on a song called "Snappin' and Trappin'." This is Big Boi, who is supposedly the more straightforward, the more conventional, the less flamboyant rapper in OutKast, both lyrically and sartorially. But what makes OutKast the platonic ideal of a rap duo is how philosophically far apart Big Boi and Andre 3000 appear to be, but also how tightly spiritually intertwined they objectively are. Speaking of Big Boi, this part of the song, "I'll Call Before I Come," has made me laugh out loud half a dozen times in the past week.

• 51:03Speaker 07

  Do you really know what it feels like to have no control over the D-spide? It's like a random pair of rebois. Or junkie, press the detox. You feel the tingling all over like commotion or the rooster box. I used to not give a damn, but now I'm making a point just to please you. You can go back and tell all your little buddies I pretty T.B. you.

• 51:17Speaker 02

  I would rather not explain the vast majority of that, nor, despite my usual custom, do I particularly want to provide the exact spelling of the song title, "I'll Call Before I Come," for you. But primarily, it's the phrase, "You can go back and tell all your little buddies," that really does it for me. The rapping on Stankonia is so dense, so lightning quick, so jubilant, so gleefully crass, so inviting but so daunting. I am somehow just realizing today that on so fresh, so clean, Big Boi declares that he's cooler than Freddie Jackson sipping a milkshake in a snowstorm. Never mind what he rhymes with that.

• 52:00Speaker 07

  Teddy, pendergrass, cooler than Freddie Jackson sipping a milkshake in a snowstorm. That's what I throw warm in the dorm room at the AU. We blew hay to athletes, might take you, but you must have me mistaken with them statements that you make, huh?

• 52:13Speaker 02

  Good gravy. Every time I listen to Stankonia again, I emerge six hours later, disoriented and exhilarated, and I've got 10 new favorite lines. Some of my favorite parts are eternal, though. You know my single favorite moment on Stankonia? When the beat drops in humble mumble.

• 52:48Speaker 02

  That's my favorite part. When the beat drops, right before Andre 3000 says, "Democratic, Republic, fuck it, we chicken nugget, we dip in the sauce like moppin bucket." That was Erykah Badu, the almighty Erykah Badu, singing right at the beginning there. Erykah Badu and Andre 3000 have a son together, a son named Seven, and I am genuinely terrified to look up how old Seven is today. If you look that up, don't tell me. Anyway, the truly massive hit single off Stankonia is about Erykah Badu's mother.

• 53:36Speaker 02

  Big Boi raps faster than you can think, but he can also screech to a halt for just a split second and hammer three simple words into your head with truly startling force. And that's what he does right there with "That's My House." Ms. Jackson is about two people who love each other very much, and they make a baby, and they dream of settling down. They dream about that crib with a Goodyear swing, as Andre 3000 puts it. And what a heartbreakingly beautiful phrase that is. A perfect encapsulation of a tempted romance under capitalism, the Goodyear swing. These guys find such vibrant and swaggering ways to describe anything,

• 54:18Speaker 02

  even the tire hanging from a tree branch in your broken dream home's front yard. These two lovers dream of being a family, but the partnership dissolves and the family fractures, and that disillusion has a catastrophic impact on the baby, of course, but it also impacts the baby's grandparents. And given that Andre 3000 and Erykah Badu, two of the greatest pop stars of their generation, had recently had a baby together and then drifted apart, Ms. Jackson is thus canonically perceived as a song delivered explicitly to Erykah Badu's mother. And thus, given how painfully personal this subject matter is, you figure Andre 3000's lyrical perspective would dominate here.

• 55:03Speaker 02

  But one thing I love about this song is the glorious good cop, bad cop routine we got going with Andre, who sounds sweet and wistful and remorseful, and Big Boi, who sounds super ultra pissed.

• 55:30Speaker 02

  I've heard this song a trillion times, but "we was divided," that three-word phrase startles me every time as well. The force of it, the indignation of it. I also love Big Boi's "yeah" right at the end. Big Boi is super pissed, and Big Boi's super pissedness perfectly tees up Andre 3000's almost unbearable sweetness.

• 56:07Speaker 02

  I remember listening to Ms. Jackson for the first time. I really do. I remember being legitimately shocked. And that shock primarily was in response to Andre's almost childlike innocence. And the silly little dog yelping and woofing right there. The sound effects bolstering this little Andre interlude verse are so disarming. The chirping birds, the rumbling storm clouds, plus the jaunty little "ah" that's about to ring off right on the word "forever." But I'll tell you the exact moment that gave me goosebumps that I still remember to this day. It's the second voice that drops in to sing,

• 56:49Speaker 02

  "You can plan a pretty picnic, but you can't predict the weather." I gasped.

• 57:06Speaker 02

  I keep typing and then erasing the words "naive loveliness" to describe the phrase, "You can plan a pretty picnic, but you can't predict the weather." But of course, it's not naive in the slightest. It's the devastating resigned loveliness of that phrase and the blunt children's book simplicity of it. "You can plan a pretty picnic." This is a rap song. This is a blockbuster, paradigm shifting rap song, animated by both dense complexity and blunt children's book simplicity. And now, Andre 3000, the best rapper ever, maybe, will utilize both that complexity and that simplicity simultaneously.

• 58:03Speaker 02

  The second "oooh," the drawn-out, ascending "oooh" in the background really pops on this Andre verse, given the relative silence all around it. So here's a foundational eternal classic outcast trick: sneak a single devastating line into a pop song, but hide it behind a playful, goofy catchphrase that seemingly everyone on Earth will use forever. So with these next four Andre 3000 lines, the ultra-famous line is "Forever, forever ever, forever ever," the actual crushing naïve loveliness there. But I submit to you that "forever ever" is really just a Trojan horse for the real crushing

• 58:46Speaker 02

  line, which is "Forever never seems that long until you're grown."

• 59:05Speaker 02

  Maybe, once upon a time, Andre 3000 thought he'd rap "Forever." He will pull this trick again on "Hey Ya," a song I enjoy very much, even if it turns out I didn't want to talk about it very much. I mean no offense. "Hey Ya" seems to be animated entirely by playful, goofy catchphrase energy, right? But "Shake It Like a Polaroid Picture," etc., is really just a Trojan horse for the entire crushing second verse.

• 59:44Speaker 02

  I know you know what Andre says here, but all the stuttering and ambient silliness deliberately obscures these lines somewhat. And so, if what they say is "nothing is forever," what makes love the exception? So why are we in denial if we know we're not happy here? Ain't as much fun without all the stuttering, now is it?

• 1:00:22Speaker 02

  Y'all don't wanna hear me, you just wanna dance. So that's what makes "Hey Ya!" the most emotionally devastating blockbuster pop song you're guaranteed to hear next time you go to a wedding. Uh, anyway, at the end of "Ms. Jackson," Big Boi gets super duper ultra pissed.

• 1:00:53Speaker 02

  I don't mind telling you that his last line there also makes me laugh out loud every time, uh, every one of the trillion times I've heard this song. Uh, Erykah Badu, who didn't necessarily love the song "Ms. Jackson," Erykah Badu did an interview with Rap Radar in 2016 and they asked her what her mother thought about the song "Ms. Jackson" and Erykah said, quote, "How did my mama feel? Baby, she bought herself a Ms. Jackson license plate. She had the mug, she had the ink pen, she had the headband, everything. That's who loved it." End quote. Families are resilient. You might not get the crib with a Goodyear swing, but you may still reach something

• 1:01:36Speaker 02

  like familial contentment, or at least detente.

• 1:01:42Speaker 02

  Well, this is awkward. Uh, the sixth OutKast album released in 2003 is in fact a double album, a double solo album called Speakerbox: The Love Below. Speakerbox's Big Boi's album, The Love Below, featuring "Hey Ya!" That's Andre 3000's album. There are a precious handful of crossover moments when Andre and Big Boi appear on a song together, but mostly they don't. Uh, but so awkwardly, due to time constraints, I am only able to offer three brief observations about Speakerbox: The Love Below. Uh, brief observation number one, don't do roses at karaoke.

• 1:02:40Speaker 02

  I know you'd like to think it sounds totally hilarious to do Roses at your next karaoke night. Roses is on the love below, but Big Boi joins Andre 3000 on this song. That's nice. Big things happen every time they meet. I bet you're imagining you'll start this song and you'll go Caroline and everyone in the room will go Caroline. That's a great call and response opening and utilizing call and response opportunities is the key to truly elite karaoke. I bet it sounds like fun to go poo poo poo poo during the chorus, but I am here to tell you that fully the last 60 seconds of Roses is just this.

• 1:03:20Speaker 03

  Crazy bitch, crazy bitch, crazy bitch, crazy bitch.

• 1:03:30Speaker 02

  Alas, as progressive and inclusive as OutKast objectively are, this sort of doodly ranker does color their music from time to time. Jazzy Bell off ATLians, I nailed that title again. I really dig that song, but it also bums me out a little. But so you don't want to be standing in front of your coworkers or friends or whatever, holding a karaoke microphone, looking at the teleprompter TV screen that gives you the lyrics and you just see crazy bitch repeat 50 times or whatever. That's going to be a dark moment for you. That's about to be the longest 60 seconds of your life. That didn't happen to me, but

• 1:04:11Speaker 02

  I did watch it happen to another guy and he handled it with a reasonable amount of dignity. But nonetheless, in conclusion, don't do Roses at karaoke. Okay. Brief observation number two. Speakerbox, The Love Below is the best selling rap album of all time, technically. It sold 6.5 million copies in the United States and it's a double album. So officially you double the sales, which means it has technically sold something like 13 million copies in the United States. If you think that's cheating, the best selling single disc rap album of all time is The Eminem Show by Eminem. So, you know, that's what

• 1:04:52Speaker 02

  you get for complaining. Speakerbox, The Love Below also won the 2004 Grammy for Album of the Year. It was the second rap album to win Album of the Year after The Miseducation of Lauryn Hill and it is also the last rap album. To win album of the year. No rap album has won album of the year in the past 20 plus years. That's funny. Also, you know what record was nominated for album of the year at the 2025 Grammys? New Blue Sun. Andre 3000's Not a Flute, definitely not a rap album. That's also funny. All of that is funny. I love the Grammys. Speaker Box, The

• 1:05:33Speaker 02

  Love Below is also OutKast's only number one album on the Billboard Album Chart. This is all part of Brief Observation, number two somehow. OutKast put out six albums total, and four of them peaked at number two on the Billboard Album Chart. Four number two albums. That is hard to do. Getting four number one albums is way easier than getting four number two albums. I assure you. And maybe you don't need this information, but I do. So, in 1996, OutKast's ATLians peaked at number two, beaten out only by Pearl Jam's

• 1:06:16Speaker 02

  No Code. I'm sorry. No offense, but that's absurd. Even Eddie Vedder would say. In 1998, OutKast's Aquemini peaked at number two, beaten out only by Jay-Z's Volume Two Hard Knock Life. Maybe. That's not quite, but it is. In 2000, OutKast's Stankonia peaked at number two, beaten out only by Jay-Z's The Dynasty: Rock La Familia.

• 1:06:59Speaker 02

  No offense, but that's a bigger than Pearl Jam. And in 2006, OutKast released their final album called Idlewild, the soundtrack to their feature film, also called Idlewild. And that album also peaked at number two, beaten out only by Danity Kane. The self-titled debut album by the girl group Danity Kane. Unfortunately, that's not as funny as I hoped it would be. I have no response to that. Also, we don't have any time for Idlewild, like at all. That's just an objective fact. I'm sorry. Brief observation about Speakerbox, The Love Below, number three.

• 1:07:40Speaker 02

  Speakerbox is better, but The Love Below is weirder and more interesting. Every time I go back to these records, I conclude yet again that Big Boi's Speakerbox is the better overall record. And I reached this conclusion at this exact moment on the song, "The Way You Move."

• 1:08:09Speaker 02

  Shout out Sleepy Brown on the hook there. He's the best. Speakerbox is better overall, but The Love Below, which is more of a Prince album than a rap album and features, to pick just one example, it includes a five-minute drum and bass version of my favorite things. The Love Below is much weirder and more interesting. And also, the single greatest individual sound on either record occurs on The Love Below. And that sound is... Oof!

• 1:08:55Speaker 02

  The oof hasn't happened yet. This song is called Spread. The chorus to Spread is excellent. Andre 3000's falsetto on Spread is excellent. But also, there's a brief instrumental interlude during Spread, once again featuring Ms. Jackson-type, childlike sound effects. But this time, these sound effects depict Andre 3000 and a young lady racing to get home so that they can engage in sexual activity. That is only my interpretation, of course, but my interpretation is correct. So, like this.

• 1:09:46Speaker 02

  So they're out of the car now, and they're gonna walk up to the house and into the house and dispose of their keys and so forth, right now. Like this.

• 1:10:11Speaker 02

  There was the oof, right there. That's the single best moment on the bestselling rap album of all time, technically, featuring one of the greatest rappers of all time who won't rap anymore, but he gave us enough, I think. Let this man play his flute and play his piano and whatever else he's got going on. Because who are we to judge Andre 3000? If he decides he's got better things to do than be the best.

• 1:10:43Speaker 02

  What a treat to be joined today by Charles Holmes and Cole Kushner, co-hosts of the Splendid Ringer podcast Last Song Standing. You can find Charles also over at The Midnight Boys, et cetera. You can find Cole over at Dissect. Gentlemen, it is an honor and a delight to talk to you both. Thank you so much for being here.

• 1:11:03Speaker 09

  We're honored. Yeah, thanks for having us, Rob.

• 1:11:05Speaker 10

  Our Villa the Killer, my, my two favorite white men, besides Chuck Sale's here.

• 1:11:10Speaker 02

  That's incredibly kind of you. Two out of three. Okay, the third season of The Last Song Standing where you picked the best song by an artist was devoted to OutKast. You've both thought and talked extensively about OutKast. You are both younger than me, but not like offensively so? Like, I'm not upset about it?

• 1:11:30Speaker 02

  How do you think younger, newer rap fans perceive OutKast? You know, are they sort of, are they sort of like a rap dad rock situation where you sort of respect them, but they don't feel present tense? Or is there still an aura around OutKast even today, even for younger listeners, where they have an enormous amount of respect? You know, still attached to them?

• 1:11:53Speaker 10

  Cole?

• 1:11:54Speaker 09

  Charles, you're younger than me, so you, you take the lead on this one.

• 1:11:57Speaker 10

  I think I'll probably have, you know, I've been called a contrarian, Mr. Negative over here, but I think my take will surprise y'all. I think OutKast is Teflon at this point. I think they're, to me, they are hip hop's Beatles where it's like, yeah, every kid is probably gonna have a phase where they try to get, like, I had that phase where I'm just like, Beatles fucked, suck. But then he's just like, oh, no, actually they had, they had jams. And I do think that, not just because the music is unimpeachable and perfect, but also because the videos that came along with it, the album art, I still think that if you go into an Urban Outfitters or you go into a college kid's fucking room, they're gonna have a poster of Stankonia, even if they weren't alive for it.

• 1:12:42Speaker 10

  Just because it is, it is on that Illmatic reasonable doubt level where it's like, okay, if I want to have taste, I, like, even if I haven't listened to this, I gotta have a shirt, I gotta have the poster, I gotta have the vinyl. Is that too far off, Cole?

• 1:12:58Speaker 09

  No, that's actually mirrors my thoughts exactly. I think the iconography of the band is so strong at this point. It is, to your point, it's like the Pink Floyd. It's reached that level of iconography and cultural just ubiquity that it's, yeah, it's Teflon, it's unassailable. And so I feel like so much has to do with it because we'll talk about their unique chemistry, I think, in a little bit here, but specifically Andre being so forward-thinking and such an alien and ahead of his time and such, such an icon, you know, the closest thing that we have to a Hendrix, I think, in our, in this generation in terms of just someone is just fucking cool. And I think his, specifically his brand of

• 1:13:43Speaker 09

  cool is timeless. And if this were, if OutKast were two big boys, right? Like, I think this is a much different conversation, because I don't think Big Boi's brand of cool has aged as well as Andre's, but their unique chemistry, I feel like, which we'll talk about, is what has sustained and has made them so timeless.

• 1:14:04Speaker 02

  Okay, so just to talk about that chemistry immediately, I guess, like, that's interesting to me. Do you think that OutKast worked so well because of the differences between Andre and Big Boi or the similarities, like, right? Like, the cliched view of them, you know, is that Andre is the space cadet and Big Boi is the down-to-earth one. And that's, you know, they grounded each other in that way. But do you think that they worked so well together because of the space between them or because they were always closer together, you know, artistically, philosophically than people thought?

• 1:14:36Speaker 09

  I think that's a perfect Venn diagram, you know, I think they're, they're the absolute perfect Venn diagram where the overlap is enough to where they sound cohesive, yet the contrast between them is what makes them so interesting. Not, not just, not just project, you know, not singular as a chemistry in terms of one single project, but also in the way in which they evolved, in the way they allow the differences to guide that trajectory and not, at least till the end, right, where they actually did splinter and you kind of see the warts on either side, I think, in the love below and speaker box when they did separate. But in their prime, at least what I consider to be their prime, it is, yeah, it's the perfect Venn diagram. I don't know, Charles, what do you think?

• 1:15:22Speaker 10

  I think what was funny, what we did our season was we did episodes on Andre's solo work, which is mostly just features. And then Big Boyz. And I think the thing that we both found is as maybe kind of overrated as Andre's run has become, when you look back at it, there was a feeling of like, oh, there is something missing. I always feel like people think that Andre 3000 was just the reason OutKast are who they are. And it was just like, when you go back, actually, when you think about who was the engineer of a lot of those early hooks, putting those bigger songs together, I think unfairly, Big Boi like is the also ran. And I think we're recording this when the clips come out.

• 1:16:07Speaker 10

  Like Pusha T has said something similar, similar about clips where he's like, yo, there was always something that in my solo career I couldn't reach and the fans wanted from me. And I always knew that I can't get there. That's malice. And I think that's true of OutKast as well, where it's just like, I, I would much rather listen to an Andre verse followed by Big Boi than just Andre by himself and vice versa.

• 1:16:34Speaker 02

  Right. Cause I think you're both, you know, I love the first Big Boi solo album, Sir Lucius Leftfoot. I know you talked about it, like I, that's far and away my favorite sort of post-outkast project, you know, across all of Andre's features. So I guess I was going to ask, like you, is hearing Andre by himself and then hearing Big Boi by himself, do you just always want the other half? Or do you think that one of them has been a little better? Like makes a little more sense as a singular unit now?

• 1:17:05Speaker 10

  I, I'm gonna be honest, there's a reason to me that

• 1:17:11Speaker 10

  Andre 3000 hasn't released a solo rap album. And that's because I don't think he's a solo rap album artist. And that's nothing against his like skills. If he made a solo rap album, we would all love it and it would be great. But I think he is very, very good in short, contained bursts of ideas where there's a reason why we love his feature work because he's going to show up on a Kanye album and deliver one of the best verses that you ever, you've ever heard. But I don't know if he can sustain that or has that much to say over the course of a, of an entire album. Because I think the thing that even Big Boi at their height was getting annoyed at is that

• 1:17:51Speaker 10

  Andre's a perfectionist. He will like toil forever over a song and a melody and an idea. And I just do think what works about OutKast is like, Big Boi can do a lot of the heavy lifting. He can get the beats together. He can, he could do the hook. He could do like, so when people are like, oh, we need the Andre 3000 record. I'm like, some people are sprinters and some people are long distance runners. And to me, Andre is a sprinter in the best way possible.

• 1:18:18Speaker 09

  Yeah. Yeah, I agree. I mean, it's, there's a reason why, for at least for me, like, when we do get the formal break in terms of Speaker Box and Love Glow being solo projects, like, there's a reason "Ghetto Music" and "Roses" are the two best songs across that entire project. And they just so happen to be the ones, they are together. And I think those two are so far and above anything else on either of those projects that it does seem to prove the point that they are better together than separate. And for all the reasons we're talking about, Big Boi being this grounded, foundational, giving Andre that foundational element that he seems to need, and Andre offering innovation and forward thinking in a way that I don't

• 1:18:59Speaker 09

  think Big Boi has ever showed us, you know? So again, the chemistry is what makes them unique.

• 1:19:05Speaker 02

  Yeah. So I don't want to spoil any aspects of the OutKast season of "Last Song Standing", but I wanted to ask, you know, did your, have your opinions changed? Your favorite songs, your favorite albums, your favorite eras, you know, over the course of re-listening to a ton of OutKast, to do that season, you know, a decade plus has passed now since they were active, you know, since they were recording, certainly, you know, are your feelings about your favorite OutKast songs changing? Or were they always sort of set in stone, you know, in the past 10, 15 years have always solidified, you know, what you know to be the absolute peaks for this group?

• 1:19:45Speaker 10

  Outkast to me was actually our hardest season to do because I realized that what makes them a good group, what makes them a great musical act is that by the day, by the month, by the year, my favorite Outkast album and song does change. Where as a kid, it was Stankonia because obviously that's that crossover moment. It's Miss Jackson, it's V O V. But then I going through the season, I was just like, I think obviously objectively their number one album is Equemeni, but A.T. Aliens is the one that I've returned to now as like a 32 year old man. And I'm just like, actually, I think that this is, I know it's the backpacker opinion, but I'm just like, that's the one I want to listen to in my car. And it's not their best raps, but to me, it's

• 1:20:30Speaker 10

  almost their purest expression before like they get very pop and they're very good at doing pop records. But there's something about A.T. Aliens to me where I'm like, fuck, this is, this is the foundation of everything I love about music.

• 1:20:45Speaker 02

  Yeah.

• 1:20:46Speaker 09

  Yeah, I think their discography is like a lot of quality discographies that where you're, it's kind of like Kendrick's in terms of like, everyone's going to have their own rankings of them, but and none of them are wrong because the discography is that strong. And so when we did the season, there's definitely like individual songs that I came to appreciate much more than I did before, particularly the song Equemeni ended up being like one of the finalists for the the whole season for us. And that was not something I predicted where the song that we did eventually land on, I think both Charles and I kind of had our eye on that. And that was kind of the one to beat and it and nothing ever eventually beat it. But every episode, we focus

• 1:21:30Speaker 09

  on one album and their discography. And when I was doing each episode and researching it and playing it, you know, constantly, I was like, maybe this is my favorite Outkast album. And my rankings just, my rankings just changed like whatever album I was listening to, even their debut, Southern Player, I was like, god damn, this is just.

• 1:21:46Speaker 10

  Southern Player is really good. And it's an album that I had underrated in their catalog because it was before my time. I think Equemeni was really when I was just like just aware of them. But Southern Player, I was just like, oh shit, they all like they always had like this is, they always had the thing.

• 1:22:02Speaker 02

  So this season, your first episode is about Stankonia. And broadly speaking, what you talk about is like the hugest hits off that record. Of course, Ms. Jackson, B.O.B., So Fresh, So Clean. Like, there's a divide between the hits and the rest of the record, right? Which is like, super long and chaotic and noisy and weird. And maybe a little more dated, you know, to 2000, you know, than the 90s records are to the 90s and so forth. Like, did Stankonia feel shocking then, you know, at the time? Or when you first came across Stankonia? And does it feel shocking to you now in the context of the rest of their catalog?

• 1:22:42Speaker 09

  For me, it's the one that did actually age the worst. And I love Stankonia, but I didn't love it as much as I remembered loving it when it came out. So it is, I think, for me, one of those albums that, um, yeah, in the moment when it came out, it felt really fresh. You know, those blaring guitar solos on that opening track and like, you know, it being hip hop group duo and that sounding so innovative and fresh in the moment. Where I don't think some of the sonics on the album, at least for me, didn't aid as well as like ATLians and even Equimini. Where I think they struck a better balance between innovative aspects and the more traditional hip hop instrumentals.

• 1:23:26Speaker 09

  But the standouts are among, the standout tracks on Stankonia are among the best songs like ever written, like ever written across all genres. So the highs are incredibly high, the lows are a little bit lower. But I don't know, Charles, what do you think?

• 1:23:43Speaker 10

  There's two perfect, there's two perfect songs on Stankonia that are so perfect that I would even argue that it just, it just cast this wide shadow over their career. Where obviously like, they do it again with the next album. But I, Stankonia and Love Below Speaker Box are kind of paired to me where I'm just like, you can feel it. Listen to, I'm like, oh, this is the end. Where it's like, these two, the chemistry of them is like, when they're both locked in, you're just like, oh, no one can match this chemistry. But it's just, you can feel, it's like, oh, these guys are not long for this musical world.

• 1:24:26Speaker 09

  And rightfully, I think rightfully so because I mean, we've now seen a lot of legacy acts, quote unquote, try to keep making records consistently and Right. Sometimes feels like a disservice to their, their legacy in some ways.

• 1:24:41Speaker 10

  I'm glad we only have one bad OutKast. Like, like going back, I was just like, hey, you know what? So many, if we look at like the Wu-Tang Clan, it's just a bunch of other just like dip and all this shit. It just, it gets sad. And OutKast has never been sad. Like even with like, we, we could talk about Andre's flute albums and all this shit. It's never felt desperate with OutKast. And I can't say that about 90% of aging hip hop groups and it just aging hip hop acts in general.

• 1:25:12Speaker 02

  Did either of you see the reunion, the 2014, you know, 700 festival, you know, grudging OutKast reunion tour? I did not see it.

• 1:25:21Speaker 10

  Did you think that I could afford that tour at the age of almost probably like 14?

• 1:25:26Speaker 02

  Okay.

• 1:25:27Speaker 10

  I mean, I remember watching like grainy, like you have to imagine like this was early, like this was still very early YouTube and shit. I remember watching like grainy footage of that shit. Um, and I just also, cause this was the time where I was reading you, Rob, is like, I feel like you were like a writer around this time. And I don't know if you remember just the feeling of people being like, I can't believe OutKast is together again. And I remember all of the writing after being like, that was a mess. Andre 3000 didn't want to be here. Prince basically had to be like, do you know who you are?

• 1:26:02Speaker 02

  Yelled at by Prince. That's a rough, that's a bad scene.

• 1:26:07Speaker 10

  And that it's

• 1:26:08Speaker 02

  You want to avoid that.

• 1:26:08Speaker 10

  That actually, that was the only moment to me where OutKast did get a little sad.

• 1:26:14Speaker 09

  Yeah. Okay. Or the potential to get sad. They didn't do it long enough. They didn't keep going.

• 1:26:19Speaker 02

  They bailed out. Right. Yeah. Yeah.

• 1:26:22Speaker 09

  Andre specifically, like you, you, you mentioned, like, it was clearly his heart wasn't in it. And it seems like Andre is the type of guy that's not going to do anything. His heart isn't fully in.

• 1:26:30Speaker 10

  And what was that verse where I think Andre has, isn't it a recent verse where like Andre's very

• 1:26:35Speaker 09

  He talks about it.

• 1:26:36Speaker 10

  Like talks about just kind of like that time and like knowing that. He's costing his best friend millions of dollars, which is also what I think is so interesting about OutKast, which is like that Coachella performance to me was indicative of what makes them different as, as artists, where I think Big Boi likes being a celebrity. Big Boi likes being a rapper. He likes stunting. He likes strip clubs. He likes what comes with this life. He loves that version of hip hop. He's that pimp. He's that figure. And Andre is like, good at being cool, but terrible at being a celebrity. Like just, like he's just, he can't, like, I was in New York when you could just walk around Chinatown or wherever, be like, hey,

• 1:27:19Speaker 10

  I saw Andre 3000. And you could just, I would never want to go up to him, which is like, he doesn't, like, he does not want this life anymore. He wants to rap and he wants to make music. I think we would have get, what do you guys think about this? Do you think if Andre 3000 was like 50% less famous, we would have gotten, gotten a solo record from him?

• 1:27:39Speaker 09

  I, I, yeah, I think so. I, there is, feels like there is a lot of weight put on his shoulders in terms of this pressure for him to continue to rap and to make a solo rap project to, to the point where it's like, almost like Lauryn Hill level of pressure. It's like, there's just, it feels impossible to, to live up to those kinds of expectations. And I actually, as, as much as me kind of would want to hear where he would go with a hip hop album now, I totally support his decision not to do it. Um, I think he's totally, if his heart's not in it, I think the right decision is actually not to do it. And it, it is to do things like, interesting

• 1:28:20Speaker 09

  things like the flute album and the piano albums, which objectively maybe aren't the greatest albums, but he has built up so much, are like positive artistic equity that we're just interested in what he has going on. And we're going to get, whatever he decides to put out, we're going to give it a listen. Um, and I think that's the best way forward for an artist like him. Like, for me personally, someone that loves people like Andre and likes artists taking chances and using massive influence to introduce people to an album like. The concept of the flute record is actually more interesting than the record itself is that, like, I want you to hear me learning how to play the flute in real time. That, to me, is an interesting artistic concept, whether it's an album you play all the time,

• 1:29:04Speaker 09

  whatever, but like, at this point, that's super interesting to me. Like, I actually am really engaged in something like that.

• 1:29:11Speaker 02

  Yeah. I agree with you guys that, like, I think we're probably better off without the Andre album everyone thinks we want. And like, Andre is 100% better off, you know, without trying to make that album.

• 1:29:23Speaker 10

  Rob, do you remember how we were all asking for a Dr. Dre follow-up? And then he dropped it on Apple and we never talk about it. Like, the whole thing has been memory-holed, you know?

• 1:29:33Speaker 02

  We don't want what we want. We don't want what we think we want.

• 1:29:37Speaker 09

  You got it. It's the classic, you leave him wanting more. If you can leave him wanting more in your career, and it's like Eminem's a good counterpoint in terms of like, we've got too much Eminem, like.

• 1:29:46Speaker 02

  We have a great deal of Eminem.

• 1:29:48Speaker 10

  You want to know what's an even better counterpoint? Have either of you, like, we have a new Kanye album that's like come out that I have not even listened to. Like, I literally was just like, I've just been like, I never thought we would get to the point where I'm like, I'm not gonna listen to a new Kanye album. And I'm like, you could not pay me, like, to just to put it on. And now I'm just like, can you imagine if, like, Andre 3000 had gotten to the Kanye point? I'm like, I jump off the building. Like, why, like, why would I fucking want?

• 1:30:15Speaker 09

  It's nothing sacred. Yeah.

• 1:30:18Speaker 02

  Okay, I did want to talk about Heiya and Ms. Jackson because I went into this episode assuming it would be on Heiya. But then, when I got to Ms. Jackson, I was just so fascinated by it and I wrote so much about it. And I found it to be such a rich text still that, like, Ms. Jackson was clearly the one to me. So I, I'm wondering if the ubiquity, you know, the pop ubiquity of Heiya especially, has affected the way you think about these songs. Like, Heiya especially, there was a point, like, everyone was sick of it. You know, and I wonder if that has affected the way we think about that song long-term. Like, do the big, do the massive pop hits that OutKast had later in their career,

• 1:31:00Speaker 02

  you know, do they age differently just because of how ubiquitous they were at the time?

• 1:31:07Speaker 09

  For me personally, no, because Hey Ya to me at this point in its in its legacy has had enough kind of breathing room from from it being overplayed because I do remember I love that song. I loved I loved it when it came out, but it did get overplayed. It just it was oversaturated like objectively. But returning to it now, like I play it for my kids. That's always my that's always my gauge for like cultural like relevance in terms of like if they like it, it's probably like has pop commercial potential and they they love that song more than even Miss Jackson. So I think there is a timeless quality to like the best pop sustaining pop records and and songs.

• 1:31:53Speaker 09

  It's going, I feel like that song, because it's not grounded in any particular sound, it'll always sound to me, it'll always sound fresh and not of an era in a way that Miss Jackson sounds a little bit more grounded, but I actually think Mr. I think you're right and Miss Jackson's the better song. Charles, I don't know. What do you think?

• 1:32:12Speaker 10

  I think both songs are still perfect. They're so great. Yes, Hey Ya is overrated, but I think the difference when you're comparing perfect songs is to me, I could argue that Miss Jackson is like a top 10, maybe top 5 hip hop record, record of the 21st century. Like it's like it's Hey Ya is good, but like Miss Jackson to me isn't just a great rap record. Like when we talk about what music has become in the 2000s and like how far that's pushed and just the layers of it from how it was made to what it means to these two guys and how it's aged. Like Miss Jackson is like, yeah, I don't know. Miss Jackson to me is like, it's a classic record. Like that's a record I'll play for my kids and they'll be like,

• 1:32:56Speaker 10

  you're so fucking old, Dad. Like you're so like you're fucking ancient, but I'm like, nah, this is the good shit.

• 1:33:04Speaker 02

  That's

• 1:33:04Speaker 10

  Like, I'm not gonna play Hey, I at my wedding, you know, but I would play Miss Jackson.

• 1:33:08Speaker 02

  That you wait, what?

• 1:33:10Speaker 09

  You know what Miss Jackson's about? What are you talking about?

• 1:33:14Speaker 10

  Whoa, you gotta keep, you gotta keep the future, you gotta keep the future Mrs. On her toes. You know what I'm saying? Like,

• 1:33:20Speaker 02

  I don't know that you do, Charles. Yeah, let's.

• 1:33:24Speaker 10

  All right, guys, you are, you know, we've been over this. Everyone knows I am on a trajectory to have multiple wives. So it's just like, it is what it is.

• 1:33:31Speaker 02

  I didn't know that, actually. I could have guessed that if I'd have thought about it.

• 1:33:35Speaker 10

  I will make songs about how I hate their mothers and how they need to get the fuck out of my face. Shout out, big boy.

• 1:33:40Speaker 02

  Okay.

• 1:33:41Speaker 09

  I think you're the only, you're the only guy to play a song about child support at your wedding.

• 1:33:47Speaker 10

  I mean, there's gonna be a lot of future also. It's not going to be the most. Guys, come on. You know, I'm trying to get people, we gotta, there's gonna be Ashic in music, some Sexy Red. Okay, there's gonna be some Miss Jackson. We're going everywhere.

• 1:34:02Speaker 02

  Okay. I'm very excited for your multiple weddings, I guess. Yeah.

• 1:34:07Speaker 09

  Miss Jackson is like the perfect encapsulation of OutKast, though, I feel like.

• 1:34:12Speaker 10

  Yes.

• 1:34:12Speaker 09

  If you could pick one song, it wasn't our winner, ultimately, but I think if you had to pick one song to represent OutKast, that that might actually be it because you get, you get, it's the Venn diagram. Again, it's it's perfect. Even in the way that each each approached the song thematically, where they're both talking about a separation. Big Boi is the resentful, kind of bitching about his baby mom. And then you have Andre, sensitive, trying to make amends, forgiving, trying to offer forgiveness to the mother. Like, it's just such a perfect encapsulation of everything we love about them.

• 1:34:51Speaker 02

  Yeah, I agree. I did want to ask about Idlewild. Has Idlewild

• 1:34:56Speaker 09

  Oh, no.

• 1:34:58Speaker 02

  risen in your, your estimation at all? Or is it just, you know, the last and objectively worst? No.

• 1:35:07Speaker 02

  We don't talk about that. We don't talk about that record.

• 1:35:09Speaker 10

  I like Mighty O. Like Mighty O is a record. You know what I'm saying?

• 1:35:13Speaker 02

  Right.

• 1:35:13Speaker 10

  Like there's like, there's like one or two records on Idlewild that I'm fucking with. But as someone who remembers watching the movie Idlewild and in real time, that's probably what, there's like foundational moments in my life that turned me into the critic I am today where it was just like, oh, things can be bad. Things could be so bad, like bad, that I'm just so upset.

• 1:35:36Speaker 02

  The joker, I see.

• 1:35:37Speaker 10

  Idlewild, watching that movie and I'm just like, this is how it ends? I was furious.

• 1:35:46Speaker 02

  I rewatched Idlewild and it's sad to me how little they interact in it. It's sad to me how like, it's, they're in two separate movies almost, you know? I, I just, it's, you know, just I cling to the scenes in that movie where they're together, like not acting very well, but they're together, right? You know, like the rest of the time, it's like, I don't know. Okay. We won't talk about Idlewild. All right. Just to wrap up, I, it was hard to imagine in the nineties, what Atlanta would become, you know, what Atlanta is now. And I wanted to ask if you hear OutKast actively in, you know, newer rap music?

• 1:36:24Speaker 02

  You guys talk so much about Future, about of course Kendrick, Drake, J. Cole, whatever, you know, like the Atlanta rap now, rap as a whole now, like, do you hear OutKast actively, you know, as an influence? And as still like the benchmark everyone's trying to reach?

• 1:36:41Speaker 10

  I mean, as someone who, when I was still writing about music, remember that?

• 1:36:47Speaker 02

  I don't actually.

• 1:36:51Speaker 02

  We're past that. We've pivoted to video, Charles.

• 1:36:55Speaker 10

  For the second or third time in our music writing career.

• 1:36:57Speaker 02

  We just pivot, we're just pivoting in a 360.

• 1:37:00Speaker 10

  But during that time, I came up during a time where like Atlanta was the epicenter. Um, and that was my generation of music. And I think the thing that I found is, It's weird how fast music moves and hip hop specifically moves because OutKast is so foundational. It's almost like where do you even begin to like talk about what Andre and Big Boi need to thug or Rich Homie Kwan or Future or Migos? It's and even if you like JID, even if you go further, just bringing melody into rap, bringing very, very tight song structure, very tight hook structure.

• 1:37:42Speaker 10

  When you look at Rosa Parks or Miss Jackson or all of these foundational records from OutKast, what you realize is this was a group like it's different from Wu-Tang Clan. Wu-Tang Clan is is just as amazing, but they're amazing in a very chaotic way in a very like this feels like a cipher. This feels like I'm trying to cut your fucking neck off. Where OutKast almost feels like we are going to show you the route to making hip hop. That's that still has everything that you want in terms of that vibrant, anything can happen energy, but can be delivered to Z100 in the most efficient way possible. And that's just not an Atlanta thing. That is, that's what the 21st century in hip hop music became.

• 1:38:26Speaker 10

  There's no Drake. There's no, there's just, there's no Drake without OutKast. There's no Future without OutKast. There's no Justin Bieber without OutKast. They are that important.

• 1:38:37Speaker 09

  Right. Yeah, the only thing I would add to that is, um, I think like all timeless kind of bands and groups and artists that we've been mentioning throughout this, this episode is that the hallmark of those, the truly timeless acts is that they are highly influential, but never imitated. Because they, they created a sound that was that you couldn't imitate. Um, and so I hear the influence in an artist like Kendrick or, or JID or, or even like an Earth Gang.

• 1:39:11Speaker 09

  And you can hear certain elements. You could hear maybe an influence and approach, but the output is always different. I think it's more of a OutKast provided a mentality of experimentation of.

• 1:39:25Speaker 09

  Not worrying about being limited into certain, you know, regional sounds. It was like, it kind of opens up a kind of freedom to an artist's approach when they're found of OutKast in a way that I think is really beautiful to have that kind of legacy. Where, again, yeah, I can't think of another song that sounds like Ms. Jackson. However, I can think of a number of artists that approach music in a similar way now, where you'll hear songs that, or even albums that kind of, even like Good Kid, Bad City feels like, for me, the closest, where I can actually hear pretty well the influence of OutKast on that album. And Kendrick has been pretty transparent about that in interviews.

• 1:40:08Speaker 09

  But yeah, I think, I think their legacy is that they, part of their legacy is that they are not imitable. And I think that's, that's-

• 1:40:17Speaker 10

  I will also say, you want to know why they're not able to be imitated? Like, 99% of motherfuckers can't rap like them. Like, if you go back to those records, like, I don't want to be the old man being like, "Damn." But like, I'm gonna be unk for a minute. Most rappers ain't rapping like they was on ATLians and Aquamanion shit. They just not. It's, we kind of lost the ability to do that in a lot of ways. And I think you see someone like Kendrick, who can kind of, like, who can get to that level. But there is just a level, I'm like, "Damn, it really, y'all not rapping like this."

• 1:40:51Speaker 09

  Yeah.

• 1:40:51Speaker 02

  Older music is better. I agree, Charles. Well said. God bless you both for being here. I will see you both at Charles's third wedding, which will feature lots of Sexy Red, et cetera. Thank you both. Thanks very much to our guests this week, Cole Kushner and Charles Holmes. Thanks very much to our producers, Justin Sayles, Christopher Sutton, and Olivia Creary. And thanks very much to you for listening. And now, let's all go listen to Ms. Jackson by OutKast. We'll see you next week.

• 1:41:34Speaker 11

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