Pod Insights DISGRACELAND Kendrick Lamar: The Streets, the Studio, and the Struggle for Mercy About this episode Before Kendrick Lamar became one of the greatest lyricists of his generation, he was K. Dot—a kid from Compton with a front-row seat to trauma, loyalty, violence, and survival. This is the story of good kid, m. A. A.d city and the real-life events that fueled it. It’s about a drive-by shooting that changed Kendrick forever. About a murder. About a robbery. About friends who vanished and others who couldn’t be saved. It’s about escaping the cycle without forgetting where you came from. And above all, it’s about mercy—in a world that rarely offers any.
This episode was originally published on August 26, 2025.
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Transcript 6,778 words · 12 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:01 Speaker 00 This is exactly right.
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0:44 Speaker 00 Sponsored by GSK, the makers of Extenture. Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor. Report if you have a parasitic infection, common cold, sinus infection, inflammation
1:29 Speaker 00 in the nose, flu or flu-like symptoms, joint pain, or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.
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2:14 Jake Brennan? Disgrace Land is a production of Double Elvis.
2:34 Jake Brennan? This is a story about a good kid. A story about a mad city. About Compton. About chaos. About drive-bys, missed funerals, red hats, blue laces, blacked-out Impalas, and the devil on both shoulders. This is a story about hip-hop. And about the rapper who didn't just survive it. He saw through it. He told the truth. And somehow, he lived. This is a story, though, about violence, and about trauma, and about the long, slow, brutal climb toward mercy. Mercy for yourself, for your city, for the people who nearly killed you, and the ones who still might.
3:18 Jake Brennan? This is a story about Kendrick Lamar. A man who makes great music. Unlike that music I played for you at the top of the show, that wasn't great music. That was a preset loop from my Mellotron called "Northern Exposure MK2." I played you that loop because I can't afford the rights to "One More Night" by Maroon 5. And why would I play you that specific slice of, "Oh, man, who gives a shit?" cheese? Could I afford it? Because that was the number-one song in America on October 22, 2012. And that was the day Kendrick Lamar released "Good Kid: Mad City" and changed the rap game forever.
4:00 Jake Brennan? On this episode, setups, the streets, near-trauma, more mercy, and Kendrick Lamar. I'm Jake Brennan, and this is DisgraceLand.
4:31 Jake Brennan? They were just kids, really. Barely old enough to be able to live on their own, to make their own mistakes, but wise enough to know that change didn't happen overnight. That it took time and energy to swing the pendulum away from the darkness toward the light. Try as one might, it's impossible to make that change with a positive mindset alone. You have to use physics. Each action having an equal and opposite reaction, you know, all the rest. You have to grab the pendulum and pull that motherfucker yourself. Fill it with your energy, your will, and your strength. And so, while Paula Oliver saw the Gangster Disciples
5:16 Jake Brennan? as a means to an end, there on the south side of Chicago, where she and Kenneth Duckworth were trying to make ends meet, the pendulum weighed heavy. She didn't want him to be affiliated anymore, even if that's all it was, an affiliation. Some adjacent relationship to a notorious criminal organization. The streets, the drugs, the tough guys like Gangster Disciple leaders Larry Hoover and King David, well, Paula wasn't about to knock the hustle butt. It wasn't a hustle she wanted a part of anymore. The Disciples were a darkness that the young lovers had to get away from if they wanted to survive. Even if that meant cutting ties, starting fresh from the bottom.
6:01 Jake Brennan? But again, they were young. They had time to do it over. Paula gave Kenneth an ultimatum. He was leaving the Disciples and they were leaving Chicago, or else she was leaving him. So Paula Oliver and Kenneth Duckworth grabbed hold and swung.
6:20 Jake Brennan? Days later, they were boarding an Amtrak train. $500 to their name, with all of their belongings stuffed into two large garbage bags. They rode the train all the way to the West Coast, to Los Angeles. More specifically, to the city of Compton, where Paula's sister helped them settle into their new life. Three days later, in 1987, they walked out of the Dominguez Hospital with their newborn baby boy. They called him Kendrick, name for the smoothest member of the Temptations, their favorite, Eddie Kendricks. They buckled little Kendrick into the backseat, and during the car ride back to their little three-bedroom house on 137th Street, they christened his tiny ears with the hip-hop gospel of "Big Daddy Kane."
7:03 Jake Brennan? Hold up. This is how the Kendrick Lamar origin story has been told, that the first thing he ever heard after the sound of his own cries at his parents' voices was Big Daddy Kane's "Ain't No Half Step" and "East Coast Bounce" booming from the shitty speakers of the family car. But this was June 1987, and the Juice Crew icon's debut album didn't even hit stores until one whole year later. So, it's highly unlikely that "Big Daddy Kane" was the soundtrack to Kendrick's first day on Earth. But, that's just a minor detail in the grand scheme of things. Because, in addition to heavy rotation staples like Marvin Gaye and the Isley Brothers,
7:45 Jake Brennan? contemporary rap music was the soundtrack to the Duckworth household that Kendrick Lamar grew up in in the late 80s and 90s. Kendrick would later remember hearing Biggie, Tupac, and Jay-Z playing during his parents' house parties, which were frequent, and which underscored Compton's deep sense of shared community. It was a community that propped up their own, like the drug dealer-turned-rapper ECE, whose debut single, "Boys in the Hood," could be found at the Compton Fashion Center, better known as the swap meet, the local flea market that sold Eazy's hot wax when more traditional outlets refused to touch it. It was a community of like-minded families, all of them trying to make sense of their own heavy pendulums.
8:27 Jake Brennan? The uncles slinging drugs, the friends tossing up gang signs. For Paula and Kenneth, it was like Chicago all over again. Only this time, they weren't going to run from it. This time, they didn't want to run from it. This was their home. This was Kendrick's home now, too. And it was the home that they taught Kendrick through their actions and through their words and through their deeds to honor values and morals above all else. Above the narrative that there was no free will, that the pistol was the only logical choice over positivity in times of real struggle. And the struggle was right here, in Compton, rolling down Crenshaw. The US Marines going slow as shit in their camouflage Humvees while the city burned.
9:11 Jake Brennan? And LA's biggest gang, the LAPD, lived that thug life out in the open. Or at least, that's what white America saw when they sat down in their faux wooden panel dens in living rooms and turned on their TV sets. The things that were happening right in your neighborhood, in front of you, shaping the person you were going to become. That was so personal, it was almost impossible to put into words. 1992. Five-year-old Kendrick Lamar pedaled his bike up the street, turning around at the top of the block and coming back down again. And the bike's plastic training wheels rattled behind him. Up against an apartment building, one of his uncle's friends, one of his uncle's associates,
9:54 Jake Brennan? the affiliated kind, was looking to unload some dope. A car rounded the corner and began to approach real slow, methodical, and then it stopped in front of the apartments. The passenger side window came down, and Kendrick stopped his bike to watch the scene play out. The affiliated associate, the one with the drugs, he looked around to make sure the coast was clear, and then he began to walk towards the car, ready for that deal to go down, make that money, now.
10:27 Jake Brennan? Kendrick jumped at the sound of the shotgun blast, hopping back onto his bike seat and flying back to his house. As the family friend lay on the ground, his chest blown open, and the baggie still gripped tight in his dead hand.
10:43 Jake Brennan? Fast forward three years later, 1995. Kendrick was eight. He was walking home from McNair Elementary, passing through the parking lot of the legendary Tam's Burger Joint. His stomach stirred a rumble as he caught a whiff of the burger sizzling on a grill. A car pulled up to the drive-thru. Its brake lights came on as the driver stopped to place his order. Right then, another man came tearing around the block, on foot, brushing past young Kendrick as he trudged through the lot with his backpack slung over one shoulder. That's when Kendrick saw the flash of steel in the man's hand. He froze, watching as a man ran right up to the car in the drive-thru, raised his gun, aimed it through the car window, and pulled the trigger.
11:32 Jake Brennan? This was the realness of Compton. It was so real that after witnessing this kind of violence up close and personal a few times, Kendrick, just a little kid, eight years old, plainly accepted it as part of his life. These weren't random acts. These were to be expected. It was the unexpected aspects of Compton life that made all the difference. Like the day Kendrick's father threw him up on his shoulders and walked them briskly down to the Compton swap meet. Not to buy an easy-yi record, but to watch history being made. There, surrounding the former Sears Building, an unassuming cultural landmark, a crowd had gathered.
12:13 Jake Brennan? And Kendrick could see lights, he saw cameras, and then he saw why. Tupac Shakur walked by in his white tank top and black fedora, flanked by Compton's own Dr. Dre, wearing a button-down black shirt, both looking fly as fuck and every bit the cultural icons that they were in this moment.
12:36 Jake Brennan? Kendrick squinted from where he was perched high up on his dad's back, looking at Dre and Pac. Both ascendant, both separated from the bullshit of the streets. At least for now. And as they shot the music video for Tupac's "California Love", Kendrick didn't know it at the time. But at that moment, at just eight years old, he was grabbing the pendulum in his mind and pulling it to the opposite direction with all of his might.
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13:53 Speaker 00 Sponsored by GSK, the makers of Extenture. Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription-maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor. Report if you have a parasitic infection, common cold, sinus infection,
14:38 Speaker 00 inflammation in the nose, flu or flu-like symptoms, joint pain or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.
14:54 Speaker 05 Hello, hello. I'm Malcolm Gladwell, host of Smart Talks with IBM. Imagine your business depends on a system you didn't build and don't fully control. For years, it works perfectly. It's fast, reliable, affordable. So over time, more and more of your operations rely on it. Then one day, the terms change. What once felt flexible now feels difficult to leave. Moving to another provider or bringing those capabilities back under your own control could take years, cost millions, and disrupt the business in the process. That's the challenge of digital sovereignty. Businesses today rely on all sorts of third-party systems:
15:36 Speaker 05 cloud platforms, data pipelines, AI models, software tools. Most days, these systems operate quietly in the background. But when something changes, like costs go up or rules shift, organizations are forced to confront how much control and flexibility they actually have. So to understand the challenge up close, I traveled to Paris to speak with IBM's Anupala Assis Anaxas CIO, Giovanni Daniele, two people who think about these questions every day. Hear the full conversation at ibm.com/smarttalks or wherever you get your podcasts.
16:22 Jake Brennan? The KFC off Rosecrans was like a beacon in the night, a greasy oasis frequented by the hungry in the stone, but also by those looking to escape the shadows of Compton for a beat. For Anthony Tiffith, the fast food joint was an easy mark. And this is not Anthony Tiffith, the music mogul that I'm talking about, not yet at least. At this moment, he's already known on the streets as Top Dog. But this was years before he founded Top Dog Entertainment, the mega-successful hip-hop and R&B label. This was the mid-'90s, and so Anthony was still just another known neighborhood threat. Hoodie up, Glock tucked, nothing to lose.
17:04 Jake Brennan? He pulled his car to the side of the street and put it in park, the big red KFC beaming down from on high and reflecting off the car's windshield. He stepped out and walked to the joint's front door with purpose. Purpose that went way beyond scoring a bucket of Original Recipe. Anthony was a known quantity, nearing 30 years old, street-certified, handled his business with a certain level of finality. And at this particular KFC, he was best known as the guy who liked to walk in, take no shit, and then take money from the register, by force if necessary. He knew this to be true as he walked inside now, and the dude working the register instantly clocked the menace, better known as Top Dog.
17:46 Jake Brennan? But this particular employee didn't seem to be phased by Anthony's presence. The guy didn't even flinch. He just went through the motions, went through this little song and dance in which Anthony ordered some food, this scripted overture to the reason why he was really there. And then, before Anthony could reach for his piece and tell the poor bastard pulling down five bucks an hour to hand over the cash and the till, the employee looked Anthony in the eye and said, "You want some extra biscuits with that? They're on the house, man." Anthony paused. He wasn't expecting this at all. He clocked the dude's tone, his lack of fear. It wasn't a softness, it was something else, something stronger.
18:29 Jake Brennan? Anthony couldn't pinpoint it at the time, but it completely disarmed him. He took his food, took the extra biscuits too, the ones that were on the house, and turned around and walked out. No stick-up, no confrontation, just this strange quiet in his chest, and a feeling that there was a bend in the road up ahead.
18:52 Jake Brennan? Anthony kept this particular story close to the vest, but some years later, news of his personal redemption, his complete 180 from street hustler to hip hop executive, was the kind of thing that teenage Kendrick Lamar was watching very closely. There were very few ways to dodge some of life's inevitabilities, but Anthony had cracked one of them: music was salvation. Poetry, rhyming, for Kendrick, that was salvation. And that was an escape hatch, just like the one he glimpsed as a kid on his father's shoulders down at the swap meet. And so when the rest of his crew ducked down an alley in the neighborhood, Kendrick ducked into a room with a pen and paper, or into a studio
19:36 Jake Brennan? with a microphone in his hand. But leaning into his music didn't immediately lift Kendrick, or K-Dot, as he was now being called, out of the fray. And he was squarely in the fray as a teenager in Compton. Even if you weren't affiliated, as Kendrick wasn't, even if you didn't identify as a Blood or a Crip, you still found yourself caught up in it all. It was impossible not to be. You were stopped for no reason by the LAPD, who were all too ready to reach for their guns when they pulled you and your friend Moose over in that dope green Camaro, and Moose took a little too long for their liking to locate his driver's license. You watched as your friends got jumped, and as your friends got shot. You watched people die in the street and in the hospital. You cradled your best
20:20 Jake Brennan? friend's brother's head in your arms, this kid that everyone called a delinquent, the kind of kid that all those talking heads on the idiot box would say, "Had it coming", but in your eyes, he was a reflection of you. And now, here he was, bleeding out from a gunshot wound, drawing his final breath, but doing so with the faith and the knowledge that you were going to avoid such a fate, that you were destined for something else, that your first mixtape was on the horizon. And so, as this kid died in your arms, he looked at you, and he said that if he didn't make it, tell his story. Sing about him.
21:03 Jake Brennan? Some would call that a burden, but shit, man, you took it as an honor. Still, that's when that survivor's guilt really started to sink in. Why in the hell were you still here? So many of the people you came up with were either locked up or six feet under. But the moment of your greatest crisis was also the moment you decided to do something about it all, in the way that only you knew how. You were, above all else, a student, an observer, an absorber, and so you took it all in. The lifestyle, the violence, Compton realness, and you wrote it all down, not to glorify it, but to preserve it and to survive it.
21:47 Jake Brennan? And you studied how the best of the best prepared and delivered their own shit, not just Dre and Tupac and Jay on your parents' stereo, but Nas and Eminem and DMX. You dissected their flows like you were performing surgery on one of those fatally wounded friends you could never save. For Kendrick, the game, the rhyme game, the spitting verses game, the mixtape game. It was a hustle, a grind, and it was loaded with this constant fear of being ignored, of failing, of recognizing in the most sobering way that you were creating music in a city where talent alone didn't guarantee success or survival.
22:28 Jake Brennan? In 2003, at just 16 years old, K-Dot released its first mixtape, which made the rounds throughout Compton. Unsurprisingly, it wound up in the hands of Anthony Tiffith, the one-time stick-up man who had just graduated from the streets and launched Top Dog Entertainment. In the Top Dog studio, which they affectionately referred to as "The House of Pain," Anthony laid down the gauntlet by playing increasingly difficult beats and asking Kendrick to get on the mic and flow. He changed the beats up on the fly, and he suddenly split into double time, anything to trip the kid up. Kendrick went hard. He met each challenge like a seasoned pro, well beyond his years. Top Dog gave Kendrick studio access, and that gave him structure.
23:14 Jake Brennan? The streets didn't go anywhere. They were still there, still calling out. But Kendrick had a different kind of crew now. Guys like J-Rock, and Av-Soul, and Schoolboy Q. The foundation of the hip-hop collective that would be known as Black Hippie. And in Anthony Tiffith, Kendrick had found a mentor. A guy who could pass down his own mistakes and his own lessons. Early on in their professional relationship, Anthony sat Kendrick down and said he wanted to tell him a story. It was a true story, but one that he rarely told anyone. It was about this one night, years ago, when Anthony went into a KFC, planning to rob the place and shoot anyone stupid enough to get in his way.
23:56 Jake Brennan? Instead, he was stymied by an unexpected act of human kindness. It sounded goofy as fuck, but, again, he reiterated that it was true.
24:09 Jake Brennan? Kendrick paused. "Wait?" he asked. "What KFC are you talking about?" Anthony shrugged. "The one over on Rosecrans. Real quiet motherfucker behind the counter. Gave me extra biscuits on the house, almost like he knew something. May have saved his life that day. Sure as fuck saved mine." Kendrick leaned back in his chair. Time came to a slow crawl. "That was my pops, Kenneth. They call him Ducky. He used to work at that joint." For a moment, Kendrick and Anthony were silent. Each thinking the same thing. That they were both at these inflection points in their lives. Because of Kenneth Duckworth. A man of morals, of values.
24:55 Jake Brennan? A man who acted the way other men wanted to act. Men who aspired to true greatness. And if it wasn't for Ducky, not only would Kendrick and Anthony not be the men they were, but the entire course of hip-hop would have been altered.
25:10 Jake Brennan? Sometimes fate doesn't need a pendulum. Sometimes, just needs a couple of extra biscuits on the house.
25:20 Speaker 06 We'll be right back after this.
25:26 Speaker 07 OnDeck is built to back small businesses like yours. Whether you're buying equipment, expanding your team, or bridging cash flow gaps, OnDeck's loans up to $400,000 help make it happen fast. Rated A+ by the Better Business Bureau and earning thousands of five-star TrustPilot reviews, OnDeck delivers funding you can count on. Apply in minutes at ondeck.com. Depending on certain loan attributes, your business loan may be issued by OnDeck or Celtic Bank. OnDeck does not lend in North Dakota. All loans and amounts subject to lender approval.
25:56 Speaker 00 Sponsored by GSK, the makers of Extenture, Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor. Report if you have a parasitic infection, common cold, sinus infection, inflammation
26:41 Speaker 00 in the nose, flu or flulike symptoms, joint pain or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.
26:56 Speaker 05 Hello, hello. I'm Malcolm Gladwell, host of Smart Talks with IBM. I spoke with IBM's Ana Paula Assis about what digital sovereignty actually means in the age of AI.
27:07 Speaker 08 AI now moves from somebody operating a system to the technology actually making decisions. So you have to have a much better visibility of what AI is touching, data it is accessing, and where.
27:23 Speaker 05 Hear the full conversation wherever you get your podcasts.
27:29 Jake Brennan? She said her name was Shereen. Long hair, gold hoop earrings, looked good in low-rise jeans. And seventeen-year-old Kendrick took one look and felt like he'd been smacked in the face. He went loopy. Suddenly, she was the only thing at this house party that mattered. They talked and he got her number. But she played hard to get. Days went by and Kendrick tried to get an address. They texted back and forth, flirting. Kendrick trying to play it cool but knowing deep down that she knew she was driving him wild. Finally, she told him where she lived and said he should come through. He borrowed the Dodge Caravan from his mom and drove it down Central.
28:10 Jake Brennan? Past Tams Burgers, past the liquor store with the sign that was always busted. Through a neighborhood that he knew wasn't neutral. None of this mattered. In his current state of mind, at this moment, there was only Shereen. He pulled up on the side of the street across from the apartment complex where she said she lived. And he got out of the minivan. And he could see her out front waving at him. His heart raced, his blood was pumping. He looked both ways and then jogged through the street to the other side. Coming up on the sidewalk, getting closer now. Already smelling her perfume, her hair. And then... Right there, coming up fast on his right, out of nowhere. Two dudes, their hoods up, hands in pockets.
28:54 Jake Brennan? They didn't ask who he was, didn't ask who he was there to see. And they were just dead set on getting their hands on him. Kendrick averted his gaze from Shereen. Where she was standing, just a few hundred feet away. He wasn't about to stick around and find out what happened when these two dudes got any closer. So he spun around and ran. His feet pounded the cracks in the pavement as he fled back across the street. A car nearly missing him, laying on the horn. And he tripped and almost hit the ground. But regained his balance and made it back to the caravan. Dove inside and peeled out, the tires screaming, his heart jackhammering inside his chest. There were no punches, no shots. He knew a setup when he saw one.
29:38 Jake Brennan? And he knew when he was being tested. Because comps and tested you constantly. Made you choose between instinct and ego, survival and pride. Kendrick passed the test that day, but he never forgot it. In fact, he wrote it down.
29:56 Jake Brennan? This story may have been fictionalized to an extent, but like all of Kendrick Lamar's stories, it's based in truth and it served as the inspiration for the opening track on his 2012 breakthrough album, Good Kid Mad City. The whole record is a coming-of-age story, a document of Kendrick's teenage days navigating Compton's streets and crews, and about how time and again, he made the choice to observe instead of act, to write instead of retaliate. And this is not softness. In fact, it's the opposite. Just like his father, Ducky, at that KFC, to be able to fight the urge to, as Kendrick himself once put it, "make the next family hurt because they hurt your family." But this is the thing about Kendrick, and it's what everyone saw in him.
30:41 Jake Brennan? Long before Good Kid Mad City was universally embraced by critics, fans, and the hip-hop world at large, including Compton's own resident tastemaker, Dr. Dre. Dre saw how Kendrick wasn't a showman. He wasn't flashy. But he had that hunger, that control. The way the kid could tell a story like he was building an entire scene and walking you through it. Transgression by transgression, body by body, beat by beat. Most remarkably, though, he did this by not following a hip-hop blueprint. He flipped the script that had been written by all those who came before him, from Dre, Snoop, and Tupac to Biggie J and Eminem. Instead of defining himself with braggadocio and persona, Kendrick turned inward,
31:27 Jake Brennan? deconstructing the streets where he remained. If not a participant in all things, then certainly a witness. The next year, in 2013, he bore witness to the entire hip-hop game, which in his eyes needed a swift kick in the ass. He jumped on Big Sean's track Control for a three-minute verse of biblical fire and brimstone, simultaneously putting respect on and calling out the names of other rappers, from J. Cole and ASAP Rocky to Mac Miller, Tyler, the Creator, and Drake. Kendrick wanted the bar raised, and he dared everyone and anyone to meet him there. The verse sent a seismic shock through hip-hop. It did what Kendrick had intended to do: to shock. But to shock in a positive way.
32:10 Jake Brennan? To shock other MCs out of a slumber and out of complacency.
32:16 Jake Brennan? Kendrick topped himself a few years later in 2015 with his album To Pimp a Butterfly, which boasted a completely different production style than his predecessor, and was heavily influenced by the music of Miles Davis and Parliament Funkadelic. It took the small scale of Good Kid, Mad City, and transposed it onto a national scale, delivering a state-of-the-union for a post-Trayvon, post-Ferguson Black America. And two years after that, Kendrick’s album, Damn, which in addition to being his second number-one album in a row, earned him the Pulitzer Prize for Music. No easy feat, seeing that in the history of the Pulitzer Prize, no artist outside the classical or jazz genres have ever won it.
32:58 Jake Brennan? As of this recording, it still holds that distinction. By the dawn of the 2020s, Kendrick had established his domination over the charts, the airwaves, and the intelligentsia alike. And he’d landed an illustrious prize, one that had always seemed far beyond hip-hop’s league. But despite all this resounding acclaim and unprecedented achievement, there was room for misinterpretation. Like those who were still on the stupid trip that hip-hop was destructive, not constructive. That it was tearing communities apart, rather than bringing them together. I’m thinking in part of the samples of news anchors you hear at the beginning of Damn, but I digress.
33:41 Jake Brennan? And then Kendrick saw an opportunity to make himself perfectly clear. He saw in the public persona of one of the rappers he targeted in his control verse: Drake. But Drake wasn’t just another rapper. He was the opposite of Kendrick in almost every way. Drake was a brand. He was a performer. He was Toronto’s slickness to Kendrick’s Compton grit. He was also the biggest star on the planet. In Drake, Kendrick saw a target. And so Kendrick, the observer, chose not to stand by and observe anymore. Kendrick got Drake in his sights, aimed, and fired.
34:42 Speaker 09 Alright, so we had Drake versus Meek Mill. A lot of people were tweeting that to me. We kinda know the outcome of that. But if Drake and Kendrick Lamar got in a rap battle, who you think would win?
34:53 Speaker 10 Gotta go with Kendrick. I'm just saying. I think Drake is an outstanding entertainer, but Kendrick, his lyrics, his last album was outstanding.
35:04 Speaker 09 Excellent, alright.
35:05 Speaker 10 Best album, I think, last year. Gotta go with Kendrick.
35:12 Jake Brennan? There's no better sign of weakness than to actually show your opponent that they've rattled you. And Kendrick knew that he had Drake good and rattled. It only took two weeks for the Canadian rapper to respond to President Barack Obama's 2016 take on social media that Kendrick would trounce him in a rap battle. Drake's comeback? Yo, Barry, you got it wrong. He was bulletproof. Yeah, right. Tell that to your ego. Tell that to your pride. Which just took one to the chest. And wait, what's up with that? Using words like "bulletproof"? Had Drake actually seen a bullet before? For real? Kendrick smelled blood in the water. Bad blood that had gotten worse over the years.
35:57 Jake Brennan? And once upon a time, there was no beef. Actually, that's not it exactly. There's always beef. It's baked into hip-hop's DNA. But once upon a time, Drake was guesting on Kendrick's tracks. And that was before Control. Before The Cypher at the BET Hip-Hop Awards, where Kendrick dropped that line about tucking a sensitive rapper back into his pajamas. Before things got really bad between Kendrick and Drake. There were all these subliminal hints they both started taking on each other. Stealth verses that, well, if you knew, you knew. Kendrick liked to think that he had better evasive maneuvers, better counterattacks when those hits came at him. And those hits didn't always arrive as expected. They were smuggled inside Trojan horses.
36:42 Jake Brennan? They were wolves dressed in sheep's clothing and all that. On Drake's 2023 track "First Person Shooter", J. Cole rapped it. "He, Drake, and Kendrick were the big three in hip-hop." Kendrick course corrected in early 2024 in a verse on Future and Metro Boomans like that. "Motherfuck the big three, it's just big me." It didn't matter if Kendrick believed it. It was good for the dialogue, good for hip-hop. And best of all, it got under Drake's skin. Kendrick didn't run marathons, but he could only assume that the high he got from fucking up Drake with his words was exactly what those lanky-ass dudes felt when they crossed the finish line. But Kendrick wasn't at the finish line. Not yet.
37:26 Jake Brennan? In April of 2024, Drake came at him, responding to the Future verse with the tracks "Push-Ups" and "Tailor-Made Freestyle." Kendrick hit back on April 30th with "Euphoria", which quickly racked up over 9 million streams on Spotify, and then with "616" in L.A. on May 3rd. And yes, the dates are important, just bear with me here. The flurry of activity was part of it. To get Drake to react quickly, to overheat, to overwhelm, Kendrick made sure he was overly prepared. He had producers like The Alchemist and Mustard working on beats in the background. He didn't stop writing, plotting, planning. And so, when later that same day, May 3rd, when Drake responded to "616" in L.A. with the track "Family Matters",
38:11 Jake Brennan? Kendrick was ready. And by the time "Family Matters" hit, the days of the subliminal diss were long gone. The gloves were off, tossed in the trash bin and rotting in the landfill. On "Family Matters", Drake accused Kendrick of domestic abuse and claimed that his son wasn't even his son. Kendrick wasn't rattled. Kendrick didn't get rattled. Kendrick got inspired. And as I said earlier, Kendrick also got prepared. So prepared, in fact, that 20 minutes later, Kendrick dropped "Meet the Grams", his response track, which accused Drake of being a sexual predator.
38:51 Jake Brennan? But he wasn't done. The very next day, May 4th, Kendrick released "Not Like Us." The track was dripping in that L.A. G-Funk bounce, and it was catchy, hooky, and at its core, it was a cold, calculated, and yes, funny masterstroke of character assassination. "Not Like Us" took everything that Drake built—the myth, the image, the sheen—and burned it down. And it delivered on the promise of the leader of the free world from eight years earlier. You gotta go with Kendrick.
39:22 Jake Brennan? The real point of "Not Like Us," however, was to separate the Drakes of the world from the Kenneth Duckworths. Those men of values and morals, men who Kendrick held in high regard and aspired to be like. And in doing so, Kendrick made it clear, this was his culture, his people, his city. If you go ahead and let some outsider, or some insider-turned-outsider—a charlatan like Drake, fuck with all that, grab onto your pendulum and swing, well, that would be a disgrace. I'm Jake Brennan, and this is DisgraceLand.
40:12 Jake Brennan? All right. Hope you dug this episode. Apple Podcast listeners, make sure you got auto downloads turned on so you never miss a drop from DisgraceLand. This week's question: What's the greatest act of mercy in music history? Okay? Was it Kendrick Lamar choosing peace rather than life on the streets? Was it Johnny Cash at Folsom? Was it Brian Wilson forgiving his father? Or was it something smaller, something personal? Text me, leave me a voicemail, 617-906-6638. You'll hear your answers on the after-party. It's up next in the feed. And if that's not enough, you want the real deep cuts, the dirt we don't put into the main feed, then become a member at disgracelandpod.com/membership. Get all kinds of free perks, including a bunch more content, because some stories are just too raw for the wide release. All right? You know what we do here? This is Mythwork. We uncover the truth, confront the story,
40:56 Jake Brennan? reclaim the music. Kendrick Lamar did that, and so do you every time you listen. Thank you, discos. Here comes some credits.
41:04 Jake Brennan? Disgrace Land was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes page at disgracelandpod.com. If you're listening as a Disgrace Land All Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to disgracelandpod.com/membership. Rate and review the show and follow us on Instagram, TikTok, Twitter, and Facebook @disgracelandpod and on YouTube at youtube.com/AtDisgraceLandPod. Rockerola.
41:40 Speaker 11 He's a bad, bad man.
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42:13 Jake Brennan? Hey guys, time to dust off your detective skills while unwinding in the Caribbean on Virgin Voyages' second true crime voyage. It's back by popular demand. This five-night, adults-only escape set sail March 20, 2027, to Grand Turk in the Beach Club at Bimini. The difference between this year and last will be that I will be on the cruise this year, along with Zeph, and he and I will be taping a live version of Disgrace Land, along with podcast hosts from Exactly Right's Buried Bones, Podcast of the Year Award winners Wisecrack, and other fan favorites. Get on this cruise with us, guys, and enjoy live podcast recordings, behind-the-scenes storytelling, exclusive meet-and-greets, and immersive
42:55 Jake Brennan? true crime programming throughout this one-of-a-kind voyage. Head over to www.virginvoyages.com/truecrime to secure your spot.
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Previous Bonus Episode: 80s Metalheads, Life-changing Concerts, and Ozzy Osbourne Next Bonus Episode: Compton, Conspiracies, and Mercy Page updated November 1, 2026 · transcript and summary are machine-generated