Aline Brosh McKenna - The Rom Com Queen Who Wrote The Devil Wears Prada

Aline Brosh McKenna is the brilliant writer behind some of the most iconic films and TV of our time: The Devil Wears Prada, 27 Dresses, Morning Glory and Crazy Ex-Girlfriend. Now, she’s back with The Devil Wears Prada 2. Before Hollywood, Aline studied literature at Harvard and worked as a freelance magazine writer in New York. She was 38 when everything changed with the release of The Devil Wears Prada - and she’s been creating sharp, funny, deeply relatable stories ever since. In this episode, we talk about writing for Meryl Streep (no biggie) the acting and magazine career that never happened and what life as an award-winning screenwriter *really* looks like. Plus: the motivating advice every single woman needs to hear. ✨ IN THIS EPISODE: 00:00 Introduction 03:15 27 Dresses and People Pleasing 04:24 Learning Not to Smallify 07:09 Writing Bold Characters 08:11 Devil Wears Prada Two Return 12:35 ‘Failed’ Acting Dreams 17:31 Working With Great Actors 23:20 Writing Meryl’s Big Speech 25:35 Scrappy Creativity Mindset 26:34 ‘Failed’ Magazine Career 29:00 Screenwriting Doors Open 32:07 Comedy Cred And Awards 35:23 Nine Pilots No Series 41:57 Ask For What You Want 💬 QUOTES TO REMEMBER: I wasn't taught to “smallify” myself by my mother, and that's maybe one of her greatest gifts. If it becomes necessary to apologise to get what you want, I think that’s okay. As long as you're aware that you're doing it... as a tactic or a strategy. Learning to withstand and be amused by failure is so key and so critical. 🔗 LINKS + MENTIONS: Devil Wears Prada 2 is in cinemas now! Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Stanley Tucci - A DWP cast member no less! The iconic Nigel…sorry, Stanley came on HTF and talked about dealing with the loss of his late wife, surviving cancer, finding love again and…failing to swim: swap.fm/l/WCW054IGNZnSnTzEXPTN Dawn French - Another genius comedy writer who talks about heartbreak, humour, adoption and meeting Jennifer Saunders: swap.fm/l/NJDrzxLKhyi6icOrxmHT 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Guest bookings for How To Fail only come from official @sonymusic.com emails Elizabeth and Aline answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [email protected] _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  It doesn't take a genius to figure this out. The minute we cast Merrill, I thought, oh, this could be awesome. And at the end of the class, he said, I've never said this to anyone in seven years, but you need to move to LA and be a screenwriter. This is what you were meant to do. Here's when I knew it was not going to work. We shot it and the executive comes up to me and she goes, you know, whatever happens with this, this thing is a real feather in your cap. And I thought, oh, we're doomed.

• 0:24Elizabeth Day?

  Welcome to How to Fail, the podcast that believes that sometimes the message is in the mess. Before we get into this conversation, please do remember to like, subscribe and follow so that you never miss a single episode.

• 0:40Elizabeth Day?

  One of the things I hear a lot from listeners is how tiring it can be when your mind just doesn't settle. And I can only imagine this feels even heavier with intrusive thoughts. It's that quiet sense of being worn down by something you never asked for and never wanted, but just can't seem to switch off. If you struggle with this, I want to tell you about NOCD because it's a resource that genuinely helps people. NOCD provides specialized treatment for OCD. And what I appreciate about their approach is how human it feels. You're matched with a licensed therapist trained in ERP therapy. That's exposure and response prevention. And over time, you learn skills that help your OCD symptoms become manageable so you can live more of the life you want to live.

• 1:26Elizabeth Day?

  If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 50 minute call to get started at learn.nocd.com/fail. Confession time. I have a tendency to postpone certain decisions for far longer than is sensible. Not the big life decisions, oddly enough, those I can usually handle. It's the smaller ones that somehow become disproportionately complicated. For me, rugs fall squarely into that category. I've known for a long time that a rug can completely change how a room feels, but I've always found sizing for a space tricky. That's why Ernesta appealed to me. Ernesta makes designer quality rugs custom cut to the

• 2:10Elizabeth Day?

  Exactly dimensions of your space. So instead of making do with something that's close enough, you're choosing something made specifically for your home. I also love the fact that you can order five oversized 12 by 12 samples for just $10 before committing, and Anesta's design team will help with sizing completely free of charge. Visit Anesta.com and order five samples for only $10 and you'll get $50 towards any rug of your choice. That's Anesta, E R N E S T A dot com. My guest today is a shaper of modern culture. The chances are you'll be able to quote a line of her dialogue, or recognize yourself in one of her characters, or you'll be able to

• 2:51Elizabeth Day?

  recall almost word for word, one of her iconic scenes. Perhaps it's Meryl Streep's impassioned monologue on the power of Cerulean in The Devil Wears Prada. It might be Catherine Hagel singing drunkenly to Elton John in Twenty Seven Dresses. Or it's Stanisic uttering the immortal line, "Gird your loins." Whatever your entry point to the work of writer, director, showrunner, and producer Aline Brosh McKenna, the chances are it lives in your head rent free. She was born in France where her mother had survived the Nazi occupation. The family moved to New Jersey when she was still a baby, and later Brosh McKenna studied literature at Harvard.

• 3:35Elizabeth Day?

  After working as a freelance magazine writer in New York City, she took a six-week screenwriting course and moved to LA where she sold her first film script by the age of 26. But it was at 38 that her life changed with the 2006 release of global smash hit The Devil Wears Prada, which earned her a BAFTA nomination for Best Screenplay. Further hit movies followed, including Morning Glory and I Don't Know How She Does It, before she co-created and showran the musical comedy drama Crazy Ex Girlfriend. Now, to the frenzied excitement of so many of us, she's returning with The Devil Wears Prada 2.

• 4:16Elizabeth Day?

  Brosh McKenna's work is funny, heartfelt, and endlessly rewatchable. Yet there's a deeper message, too. A spotlighting of powerful women who might be misunderstood by others, but who come to understand the important balance between selfhood and connection, between work and love, in whatever form that love takes.

• 4:39Elizabeth Day?

  Being funny, Roche McKenna has said, means you're honest, almost to the point of transgression. You're saying the thing that isn't supposed to be said. Eileen Roche McKenna, welcome to How to Fail.

• 4:52Speaker 00

  Thank you. Everybody always like kvels after your introductions and I feel all tingly.

• 4:58Elizabeth Day?

  Oh, well, it is such an honour to meet you.

• 5:00Speaker 00

  Thank you.

• 5:01Elizabeth Day?

  Thank you for all of the work that you've put out into the world. It really has meant so much to so many of us. And I know we're going to talk about The Devil Westprada, obviously, but Twenty Seven Dresses was such a great movie.

• 5:14Speaker 00

  Thank you. I wrote that. It was inspired by my best friend had been in about 12 or 13 weddings at the time that I pitched that. And I thought that was psychotic and fascinating. To me, it was about being a people pleaser, which is a very common thing that happens to women. And it was interesting, as we were trying to get it made, people, and particularly male executives, really balked at that idea, which they thought was about weakness.

• 5:40Elizabeth Day?

  Wow.

• 5:40Speaker 00

  But I think that that ability that women have to sort of shape shift and understand intuitively what needs to be done in a moment is a is a strength. And I think she's a very strong character, actually. That really is what that movie is about to me, which is how you end up being so beloved by so many people. And is there a cost to that?

• 6:03Elizabeth Day?

  So interesting. Have you had your people pleasing years?

• 6:08Speaker 00

  You know, it's funny, that's the one that is the least like me. And that movie is written from the point of view of the best friend, Judy Greer, in a funny way. If you look at it, even though she's not in every scene, the movie, the movie's POV on her is, what are you doing? I'm half Israeli, half French North African. And we had very honest, outspoken set of parents in our family. My brother is too. And so I was not taught some of the American, but both my parents are immigrants and we were raised in New Jersey, which is just was a strange sitcom. But I wasn't socialized in girls having to please others. My mother was a grand dame.

• 6:52Speaker 00

  Actually born quite poor, but like all French women, she was a queen with Hermes. They sort of somehow hand you Hermes when you're, you know, not, not anymore. Didn't used to cost what it costs now. For example, every dating story my mother ever told was, you know, I was very beautiful and I met a man and he wanted to marry me and I said, no, you are not handsome enough. You are not rich enough. So all of her stories were very about dating were very grand and they always encouraged both my brother and I to be very outspoken. And so I'm fast, I'm fascinated anthropologically with the sort of apologies and the abnegation

• 7:36Speaker 00

  of self that women are taught in America. It's really interesting because I think people think of Americans, women as being sort of brassy, but we're actually taught a lot of dissembling. So often I work, when I work with younger female writers and I'll hear them saying, well, I, you know, this is probably terrible and we, we don't want to do this, not this, but you know, this, this, this is not what we want to do, but, but maybe, and I had a crazy idea and a bad idea and, and their legs are cinched together, much like ours are to sort of occupy the least amount of space on a chair. And then, um, boys are really encouraged to splay in every way imaginable.

• 8:18Speaker 00

  And, um, I wasn't taught to sort of smallify myself by my mother. And that's maybe one of her greatest gifts.

• 8:27Elizabeth Day?

  That idea of women littering their ideas, their emails, their communication with mitigating words.

• 8:34Speaker 00

  Yes.

• 8:34Elizabeth Day?

  I relate to it so deeply. And something that helped me almost overcome that, I'm not entirely there yet, was writing a bombastic male character in a novel of mine.

• 8:45Speaker 00

  Hmm.

• 8:46Elizabeth Day?

  And I realized that if I could imagine this bombastic, unscrupulous billionaire man, then it was within me to lean into that.

• 8:55Speaker 00

  Right.

• 8:55Elizabeth Day?

  And so I set myself this challenge of acting 5% more like that character. Have you found that writing characters has helped you?

• 9:05Speaker 00

  Well, I mean, no one gives you more permission to speak your mind than Miranda Priestly. So that was, I always loved that about that character. If it becomes necessary to apologize to the furniture a little bit to get what you want, I think it's okay, as long as you're aware that you're doing it. As a tactic or a strategy, I think it's completely fine, the exclamation points and the... Listen, I also think, you know, being kind and stopping to praise someone, which are, again, let's say typically female attributes are great in the workplace. But yeah, anytime I, the two, Miranda Priestly, and then I wrote a movie called Morning Glory

• 9:47Speaker 00

  with Harrison Ford playing an aging news anchor who was really outspoken. And that was a ton of fun and I could just make him say anything. And I think there's a tremendous amount of wish fulfillment in writing those characters because we all want to be able to do that. We all want to be able to be cranky.

• 10:07Elizabeth Day?

  The Devil Wears Prada, I refuse to believe it's 20 years since that movie came out, but apparently it is. That's what the chronology of time tells me. You were 38 when that movie came out, so 20 years on now. I'm just really interested in how different you feel as a writer.

• 10:27Speaker 00

  Well, I thought I was ancient. I mean, I felt very ashamed that my first, I had made two movies before and a bunch of TV stuff, but it was, you know, my big, first big successful thing. And I, I kept thinking, my God, I'm, I'm a 38-year-old mother of two, wife and mother of two, and it's taken me so long and this is so embarrassing. And now, of course, I look at 38-year-olds and they seem like little babies to me. I don't know why I wasn't more generous with myself, but it felt, you know, I had been working for 15 years. The world has changed so much, twas ever thus. You know, the world changes and so much had changed for these characters. And for a long time,

• 11:12Speaker 00

  We weren't going to revisit it. And then every industry that is touched by this movie, fashion, publishing, journalism, has just all been turned upside down in the last five years especially. And that's how it became more and more interesting to us to sort of talk about, you know, what do you do when the world is changing all around you and obviously happening in the movie business, but kind of everywhere, you know, because I did always think about over the years where those characters were and what they would be doing. And now it's they're presiding over tremendous change, the managing a downturn. So, you know, it's as fun a movie as you can make about managing

• 11:57Speaker 00

  downturns, I think. And

• 11:59Elizabeth Day?

  Was that the pitch?

• 12:00Speaker 00

  Yeah.

• 12:01Elizabeth Day?

  Did you find it at all intimidating, given the success of the first movie, that idea of coming in with a sequel? Do you have moments of self doubt?

• 12:12Speaker 00

  Oh, my God.

• 12:12Elizabeth Day?

  Where you're like, am I funny anymore?

• 12:15Speaker 00

  To get the band back together. So it started with me over the years because David Frankel, who directed the first movie, and I have stayed friends and sort of things would happen that felt like were pertinent to the Prada world and we would chat about them. So it started to be more and more interesting to us. And then we heard that Merrill was open to hearing some ideas. And at that point, I had accumulated quite a lot of them. So as I turned to these collaborators from 20 years ago, and it seemed like there was more to explore. And then as we, you know, as the script went to Anne and Emily and Merrill and Stan, and we were able to sort of talk about, you know, what was relevant

• 12:58Speaker 00

  and where these folks were. And it felt like it made sense.

• 13:02Elizabeth Day?

  You probably can't tell us anything, but can you tell us anything about where The Devil Wears Part Two meets all of these legendary characters?

• 13:11Speaker 00

  It's funny because the trailer that they released in which Miranda doesn't remember her, I saw some people saying, oh, does she, you know, she's sundowning, she has dementia. And I'm exactly the same age that Miranda Priestly would have been in the first movie. And the idea that 20 years from now, that I would remember somebody who I spent a year with, even if I wrote them a recommendation letter, it's believable that, you know, it's somewhere in there. But yeah, she doesn't remember her. When she sees her, it struck me as tremendously funny because, you know, the idea of the first movie was always that

• 13:56Speaker 00

  your boss is really interesting to you and you are not as interesting to them.

• 14:00Elizabeth Day?

  Yes.

• 14:00Speaker 00

  And so I always felt like the first movie was tinged with Andy's perception of her, who she was, but also Andy's perception of her. And similarly, in this movie, there's the reality, but it's tinged with Andy's perception of who this woman is now, now that she's a woman in her 40s. It was sort of like I discovered an old dollhouse and I got to go back there and, and set that all up again.

• 14:28Elizabeth Day?

  Well, what a privilege and a joy it will be for us all to watch it. Let's start with your failures. Your first failure is not being talented enough, these are your words, to be an actor or a singer.

• 14:39Speaker 00

  Well, I have video evidence of this, sadly. When I was a kid, I was good at school, but I had trouble finding my people. And I didn't have a ton of friends. And I was quite shy, which no one who knows me now can believe, but I was quite shy. So for some reason, I decided that because I was shy, that I should go out for the play and that that would help me with my shyness. And so I auditioned for a play in fifth grade. And so I did this play, I had one line, but I really loved the people. And I felt like, even though I wasn't really getting very big parts, I loved being around the people and

• 15:21Speaker 00

  the process. And I felt like, oh, these are my people. And then I moved to a smaller school. You know, as Darwin would dictate, there were fewer people there. So I got better parts. And when I was in ninth grade, I got a lead. And so I really, I had to sing a lot in front of people. And I just did it. And I really loved being in a play, being part of it. I'm friends with a lot of performers. And when you turn the light on, people who are really performers, they, they come to life. That's where they belong. And I never quite felt that. But I felt like this zone of show people is where I should be. So I kept trying. And I kept auditioning. Because I was in this really small high school, they kind of let me sing and perform on the regular. So I, I sang at my graduation, which was

• 16:06Speaker 00

  hilarious, with my friend, John. And many years later, I said to John, you know, I really don't sing in tune very well. And he said, now you're, now, after you've sang in public so many times. And I would have loved to, if I had a magic wand, that would be the thing I would know how to do is to like, be a great singer. So I went to college. And the way they do it at Harvard is that you audition for all the student plays are student run. There's no faculty. And you audition for all the plays in the first week, common casting. And there's about 50 plays. They're all student runs. They're all over the campus. So those seem like good odds. So I went and I auditioned for, you auditioned for all the plays at the same time. And then I went there the day that all the cast lists

• 16:49Speaker 00

  were posted. And there was, you know, 50 cast lists, which is a good amount. And there was another kid who was a freshman. And I watched him, his name appear on this. And like, I think he got like, seven leads. And I didn't get a single part in any play, which is kind of hard to do. Like, I shot the moon of bad acting. And so I really had to lick my wounds. Again, I just felt this pull towards. Theater people and people who wanted to sell stories and creative people. And so I ran the light board. And I was a stage manager and I did stuff like that. And then I had applied and forgotten, I applied to direct a play and forgot that I had applied.

• 17:30Speaker 00

  And I got a letter one day saying, you have $500 to put on a play in the freshman union. So I did that and I really found I really enjoyed marshaling a group. And so that's what I did in college is I directed a lot of plays. And wrote a little bit for the newspaper, but I never, you know, I think. I never have lost the sense of wonder that I have around actors and performers. I did Crazy Ex Girlfriend with Bloom, who was my, Rachel Bloom was my creative partner. And I knew what she was capable of. So writing for someone who I knew what she could do and what she would crush, you know? And then that's, that was, that's been true.

• 18:13Speaker 00

  I mean, just imagine writing lines for Harrison Ford, you know, just.

• 18:17Elizabeth Day?

  Yeah, well, Meryl Streep.

• 18:18Speaker 00

  And then, and then imagine writing, you know, lines for Meryl Streep. And knowing that you're going back to writing for these four people who are, you know, in the 20 years since have only become more esteemed, you know? So I've never lost the sense of being tickled by great acting and singing. Although there's not a lot of singing in these movies. Because I was never able to do it. I did a cameo on Crazy Ex Girlfriend with Rachel and I had. We came, I played the prosecutor and I came out and I said my line and she just doubled over laughing. And I said, what's wrong? She goes, that was so bad.

• 18:59Speaker 00

  And I think sometimes when people get into trouble, it's because they hold on to dreams that are not related to their aptitudes. And I think your aptitudes and your dreams are in a conversation with each other and with the world. And I think because most people enjoy doing well, finding something that you're good at is also part of finding out what you're not good at.

• 19:22Elizabeth Day?

  Yes, that's so well put.

• 19:28Elizabeth Day?

  When you work with these legendary actors, I mean, you mentioned a few of them there. I know you've already said that what you notice is that they come alive under the spotlight.

• 19:38Speaker 00

  Yeah.

• 19:39Elizabeth Day?

  Is there another thing that links Meryl Streep, Harrison Ford,

• 19:43Speaker 00

  Right.

• 19:43Elizabeth Day?

  Rachel Bloom, Stanley Tucci, that you can now see, oh, that's, that's how they prepare. That's what makes them different.

• 19:51Speaker 00

  You know, everyone's very different in terms of process. And one of the things that I learned from working with actors is I also made a movie. I directed Reese Witherspoon and Ashton Kutcher in a movie. And

• 20:06Elizabeth Day?

  We Bought a Zoo.

• 20:07Speaker 00

  That, that movie is called Your Place or Mine. It's a Netflix movie.

• 20:12Elizabeth Day?

  Sorry.

• 20:12Speaker 00

  And it's a romantic comedy, but I did also work on We Bought a Zoo. What I learned is that everyone is really different. And what, one of the things I enjoy is meeting an actor's process where it is. Some people like to rehearse, some people don't like to rehearse. Some people like to talk about the material a lot, some don't. Some like to know exactly what they're doing and some don't. And I actually love that. I love sort of finding the person, the artist where they are. And I don't have rules ever as a director or producer or anything, which is like, this is how we do. Apart from some larger things of like, we don't run and we don't yell. I don't have set precepts about how we need to work. So if an actor wants to talk exhaust, wants to send me a six page email after a run through, great.

• 20:57Speaker 00

  And if they don't want to talk, great. And every actor you just mentioned is completely different. The movie with Harrison had Rachel McAdams and Diane Keaton in it, all very different actors.

• 21:07Elizabeth Day?

  So were Reese and Ashton different? Is that why you mentioned them in this context?

• 21:11Speaker 00

  I just was remembering that like Reese has a different, I would go to Reese and I would say, I would say something about the character and she would say, am I saying that or am I thinking that? And I would say, you're thinking that. And she was like, okay, cool. You know, like she was.

• 21:28Speaker 00

  And she also likes to do a scene in the moment, right as you're about to do it, and then, and then talk to me. And so that was interesting because it makes it more alive for her. Like, she's extremely prepared, and then you come and you do it. And then we would look at each other and be like, oh, we'll go this way. In fact, when we were making this movie, we shot some of it in New York. And I remember we went out on the pier, and Reese did the scene. And then she turned to me and she goes, I don't think that works. And I was like, I know, I don't think that works either. And I took a piece of paper, and I put it on my knee, and I wrote a new scene, and I handed it to her, and we looked at it, and then we did that. And then with Rachel, you know, Rachel was so, is so flexible

• 22:11Speaker 00

  that you can sort of say to her, like, do this line and hold your arm out at this angle. And she's like, thank God, it's doing it. And, I mean, I could go on and on about

• 22:19Elizabeth Day?

  I'm so fascinated by you doing that.

• 22:21Speaker 00

  How brilliant they all, how brilliant all of these folks are. I mean, Emily and I, I love to run a joke into Emily Blunt. That's my favorite thing to do is she'll do a take, because, because when you're on set, and the actors have done a joke a couple times, and you feel like you have it, then it's really fun. My favorite thing to do is run in a new joke.

• 22:41Elizabeth Day?

  Does that just mean you're throwing it in from the side?

• 22:43Speaker 00

  I'll just come in and say, what about this? You know, like, maybe you say this this time, as long as the director, as long as David feels like he has it. And so, that's absolutely with Emily, often I'll run out and give her a joke, and then the problem will be, she'll say to me, I just don't know if I can get it out without laughing. And that's just the best, is seeing her, like, do the line, and then just bust out laughing after they say cut. On the first movie, I remember Stanley was about to do the scene where he tells to, Andy, you deign to work here. And I remember I said to Stanley, do you want me to make any adjustments, or, you know, change anything for you? And he said, no, I'm good. And that was like,

• 23:21Speaker 00

  As meaningful a collaboration to me, knowing, okay, that's where the target zone is for him, as it is when an actor sometimes wants to come over and really like go through every scene. And then in both Prada movies, Annie is in almost every scene and has to carry, you know, the entire soup to nuts story. I mean, literally soup to nuts. And so I always have worked really closely with Annie about the complete arc of that character because it's, it's so much work for one person. It's so much through the scrim of her perception.

• 23:57Elizabeth Day?

  Before we get on to your second failure, your collaborative approach with actors led to one of the great speeches of all time in movie history. The speech about cerulean that Meryl delivers as Miranda Priestly, which goes to the heart of so much of what fashion represents to so many of us and is so beautifully done. Can you tell us about how that came about?

• 24:23Speaker 00

  Meryl had looked at those, that those few lines had been in the script for a long time. And I would say maybe like five or six days before we shot it, David said, Meryl wants to talk about that scene and she feels like it could be more and it could be built into a speech. And I started working on it and I started making it longer and longer. And then, um, and then I, there was a day where, so I had little kids when we were making the first one. They're grown men now, but they were little kids and I, it was on a weekend day. So I went to the Starbucks and I was sitting there and I was emailing the speech to David, who was emailing it to Meryl and then getting notes from Meryl and then conveying them to me.

• 25:06Speaker 00

  So for instance, I said, had written the, in the section about blue, I sent a list to him that said, um, lapis, azure, cerulean. And she picked cerulean. She said, great, you know? And it, and as we worked on it, it got larger and larger and larger. It wasn't really meant to be so much of an aria. But I thought, you know, knowing how movies are and this, you almost, you do this often, which is like, okay, well, it's going to be, I'm going to write this thing that had been three or four lines will now be a page and a half. And so I kept building on it and it was really thrilling, you know, knowing that it was going pinging for Meryl back to me and getting her feedback. And then I've

• 25:49Speaker 00

  sent it back and said, you know, here's this big chunk. I don't know, you can cut it down. You do use whatever you want or and they shot all of it and it's all in the movie. On that first movie, I was so eager that when I I tried to be on set as much as I could. And then when I wasn't there, I would wake up in LA, I would wake up at their rehearsal time. And then David would call me after the rehearsal and say, what about this line? Or maybe could you improve this or you could prove that? So I sleep clutching my phone and then get up for the rehearsal and then write a bunch of alts and send them to him. For example, the gird your loins line that Stanley has, I think I sent David eight things for that. But I'm the gird your loins, I believe Stanley came up with. I'm pretty

• 26:34Speaker 00

  99% sure Stanley came up with it. And I was trying to beat it. And I was, you know, sending in stuff, stuff to David. I wish I still had those emails. And then at night, I would read the scene for the next day and send him alternate lines and suggestions. I was obsessed, like And you had two young children. And I had two young children. And by the time the first movie wrapped, I had pneumonia, my husband had pneumonia, my son had pneumonia, our babysitter had pneumonia. I kind of ran myself into the ground. And but I was, I had, I mean, it doesn't take a genius to figure this out. The minute we cast Meryl, I thought, oh, this could be awesome. I mean, I thought

• 27:19Speaker 00

  it was fun and great. And I loved writing the script and I loved working with David. But, you know, I this, the second we cast Meryl, I remember I was so astonished when David told me that I sat down on the Sidewalk in Larchmont and start crying because I was like, oh, there's a big wave coming and I gotta stay on this wave. And so I just worked around the clock to make sure that I was, you know, putting in. So that's why it was like Saturday morning, run to the Starbucks and sit there as long as you can, sending in alts. And I sent in alts for a lot of stuff.

• 27:50Elizabeth Day?

  I think it's so wonderful that people get to hear this, the kind of scrappiness of the obsession, the fact that you wrote in a very unprecious way. You just had to grab the time, go to Starbucks, put some ideas down. And I think it's so refreshing to hear that as well, because I feel that so many people have a dream to write or create in some way, but they fear that the conditions have to be perfect first. And there's so much fetishization of routine now, that idea of sort of getting up and having your morning pages and your matcha. And I think it's so great to hear that actually some of the best ever movie dialogue came out of you in that way. And I find it interesting that

• 28:34Elizabeth Day?

  your second failure is your failure to be a magazine writer.

• 28:39Speaker 00

  Oh, my God.

• 28:40Elizabeth Day?

  After you graduated college. So tell us about this.

• 28:43Speaker 00

  Absolutely. Like, and it's the formative, it's the thing that got me the job because I told David about it when I first met him. Okay, so I graduated from college, my roommate.

• 28:52Elizabeth Day?

  Magna cum laude.

• 28:54Speaker 00

  Magna cum laude, indeed. And not Suma, though, importantly.

• 28:58Elizabeth Day?

  Oh, is that above?

• 28:59Speaker 00

  Suma's above. And my father was a furious, because one of the girls I went to second grade with was Suma, and he was real mad. So I graduated, my roommate was writing for the Harvard Lampoon. I wasn't, I was writing for the paper and directing plays. Having graduated from Harvard and written for three months, we wrote a book proposal and sold it right away. Felt like we were on a good run. So all I wanted to do was be a New York Magazine writer. I just, I grew up reading, obsessively reading New York Magazine. That was my number one. I wasn't as much of a New Yorker reader, but I always had a subscription to the New York Times, even in college, and I always read New York Magazine. And I just

• 29:43Speaker 00

  thought that was going to be the coolest thing ever. So my roommate and co-writer, we started trying to get magazine jobs together because we'd written this book, which seemed good.

• 29:56Speaker 00

  We could not get arrested anywhere. We wrote proposal after proposal. We sent proposals to every magazine. It seemed to me like a completely closed world. And, you know, having been the child of immigrants, my parents really didn't know what was up. I mean, my mother tried to hand out sliced red and green peppers on Halloween. She really, they just didn't know what was up. Like, when I went to Harvard, I thought, I didn't realize other people there would know other people. I thought they were all like me, just, you know, special weird little carrots pulled out of the ground. And then I got there and I was like, oh, this lady across the hall knows 50 people here because, you know, she's in this world.

• 30:38Speaker 00

  So I have often had the experience of feeling like I'm entering a closed world and I don't know what to do. And magazine writing seemed like it was also founded on parties and relationships and connections. And I had no idea how to do that. I didn't know what parties to go to. I didn't know who to be friends with. And I had had success in my life by like, there's an application. You fill it out and you get the thing. You know, you want to write a book. We wrote some chapters. We sent it in. We got a book. But magazine publishing was not like that. And so I, my roommate then got a TV writing job and she left to go to LA.

• 31:23Speaker 00

  And I thought, well, take a screenwriting class. I'll start with the thing I love the most because I always really loved movies. I'll start with the thing I love the most and then I'll kind of bump down into whatever form of writing finds me. And the teacher really, right away, was like, oh, you have some promise here. And at the end of the class, he said, I've never said this to anyone in seven years, but you need to move to LA and be a screenwriter. This is what you were meant to do. And it was one of those conversations with the world. It was like, well, I guess there's something here. Now, you know, I came out to LA and then banged my head on lots of doors, but it was not, the magazine thing was like, there's no way I can describe how

• 32:06Speaker 00

  fruitless it was. Like, no one liked our ideas. No one wanted to meet us. No one wanted to invite us to a party. And, and then when I started screenwriting, it was like, oh, I, I gave the script, oh, I'd like to be your agent. Um, you know, uh, uh, you're gonna get a blind deal at Universal. Like, I started to just, you know, squinge some doors open. So I felt like I had been Andy. Um, and in the beginning of the movie where she sort of offered like, oh, because I also tried to temp. That was also a disaster. Oh, my God, disaster. But, but when I got the book, I thought, oh, I, I understand her. I think we all go from being Andys to Mirandas over time. Get much more crankier when we get the wrong coffee order.

• 32:51Elizabeth Day?

  Everything that you say, I am relating to extremely deeply for reasons that I, there's not enough time to go into, but I hope I can have another conversation with you another time, maybe over Martini, about the similarities that I am experiencing hearing you talk. But I think that outsidership is what gives you your great gift of being able to see people as they are from the position of observer, but also the other part of your gift is the a bit of he to draw humor from that.

• 33:23Speaker 00

  Yeah, you also, you develop, I think, a lot of, definitely a lot of the people who founded Hollywood were either immigrants or the children of immigrants. It tunes your ears to slang and, and things like that, because, you know, everything you have is learned, because my parents didn't, didn't know the current lingo. And I always was hilarious when my mother, my mother latched on to the phrase, I'll catch you later, at some point. And that's what would happen is my parents would latch on to a, a phrase, a slang, and then use it for the rest of their lives. So my mother said, I'll catch you later, from like 1980, for the rest of her life. And when I lived with the roommates and my mother would call and she would say, okay, Aline, I will catch you later. And all of my friends

• 34:08Speaker 00

  said that. Um, but you get very tuned to rhythms of speech when you are in a, in a house where people are searching for words.

• 34:18Elizabeth Day?

  Searching to fit in, searching for the key to the code. Before we get on to your final failure, I wanted to, I wanted to ask you about comedy specifically, and being a female writer of so much great comedy. Do you think it is taken seriously enough? Because I found it shocking, Helene, that you were not nominated for an Oscar for Devil Wears Prada, but Borat was.

• 34:44Speaker 00

  Well, I was dumb. I didn't get any help. I was very afraid and I, I did not know what I, I will say that the BAFTAs were the same night as the Writers Guild Awards and I was like, gee, do I, do I go to the BAFTAs and mingle with these, like, the most fabulous people that I've worshipped for so long? Or do I go to the basement of the Beverly Hilton with my fellow writers, God bless, who I've spent a lot of time with on various picket lines? I know exactly what that shape is. And so had to go be with my folks in the basement, freezing cold basement of a hotel. Don't regret it, but would have liked to have been at the BAFTAs. Because I had friends in the improv group, because I know people out here who really do comedy comedy,

• 35:27Speaker 00

  like, you know, friends who worked on The Office or worked on Friends or worked on, I don't, I understand that I write comedy and I write funny lines, but I don't think of myself as being in the comedy world in the way that like, Bloom is a stand-up, Bloom is an improviser, Bloom knows all the people at UCB, and I've met a lot of comedians through her and I know a lot of comedians. But I think of what I do as, as the, the bad version is like drama with jokes. I don't fetishize comedy cred.

• 35:59Elizabeth Day?

  Yes.

• 35:59Speaker 00

  The way a lot of comedy people do. And that started in college at The Lampoon. So I wrote a funny column for the paper and I directed comedies, but I wasn't writing sort of highbrow comedy, which is what The Lampoon was, which is like this really like brain, heady comedy. The things that I have always found funny are things that come from emotion and heart and soul and embarrassment and like really immediate human experiences.

• 36:26Elizabeth Day?

  But do you think you should have won more awards? Because I do.

• 36:30Speaker 00

  No, I, I don't, it's, I can't even explain to you how little I ever. That's wild to me. The only thing I ever worked on that I thought give us the awards was when I worked with, well, I knew Meryl was going to get nominated. The first day of Prada, we shot the scene where Andy comes to the top of the stairs and Miranda whirls around and looks at her. And it was so terrifying that I took my arm and I whipped it out and I hit David in the front of the chest like we were in a car wreck. That was my first instinct. I went like that and I like thwacked him off the, I was like, oh my God, there's Miranda Priestly. And I, after that take, I said to him, I mean, she's going to get nominated. I knew that.

• 37:14Elizabeth Day?

  There are so many things I wish I'd known when I started this podcast and my production company, Daylight. Like, why am I spending hours trying to make a website look good? Why am I designing everything from scratch? And why am I spending all my time just doing admin? What I really needed was one place that could do all of this for me. Enter Shopify. Shopify has beautiful, ready-made templates that make your website look polished without needing to become a graphic designer overnight. Its AI tools can help you get your site up and running quickly, and Shopify Checkout makes it really easy for customers to actually go from, ooh, I like that, to, yes, I'll have one. If Shopify

• 37:55Elizabeth Day?

  had existed when I started out, I could have saved myself a lot of time, stress, and some rogue design choices. If you're ready to hear the

• 38:05Elizabeth Day?

  of your first sale today, head over to Shopify.co.uk/fail to start your free trial today. That's right, start your free trial at Shopify.co.uk/fail. Your final failure

• 38:19Speaker 00

  Yes.

• 38:20Elizabeth Day?

  is co-writing nine TV pilots in the 90s

• 38:23Speaker 00

  Yes.

• 38:24Elizabeth Day?

  and never getting any on the air.

• 38:26Speaker 00

  None. So when I was 25, I was so miserable writing by myself, writing movies by myself, which is what I had been doing. And I met a TV writer, his name is Jeff Khan, who's a really brilliant guy. And he'd been writing on the Ben Stiller Show. And someone put us together to write a pilot together. The executive named Sasha Emerson was looking for a man and a woman to write something together. And we met and 10 minutes later, he called me and said, it's me. And we wrote together for five years. And we had a good amount of success selling these pilots and we shot three of them. But it got harder and harder and harder and harder.

• 39:10Speaker 00

  We wrote one. It got shot, but it was a planted spinoff of another show. And it was the first time. So the first time I ever wrote anything that got shot was that a planted spinoff. It's very boring. I can, but it was, it was, it was shot as an episode of another show. But I'd never been on a set before. And I had to pretend that I had. He's five years older than me, so I was 25, 26, and he was 30, 31, which I thought was ancient. Could not believe I was working with such an old person. But when I got there, like, I didn't know that they gave you lunch. I thought that lunch was the crafty table, which is like the snack table. So I was like, wow, so they eat like fruity pebbles for lunch? That's interesting. They eat cut up carrots for lunch?

• 39:55Speaker 00

  That's so interesting. I didn't realize that there was like later, they were going to give you hot food. That's how stupid and lost I was. And I obviously was not going to tell anyone that I didn't know what I was doing. Here's when I knew it was not going to work. We shot it and the executive comes up to me and she goes, you know, whatever happens with this, this thing is a real feather in your cap. And I thought, oh, we're doomed. We're so doomed. It's just like a thing someone only says to you when you're sort of like being flushed down the toilet. And then we did another pilot.

• 40:30Speaker 00

  That was a two-person comedy about a guy who was a kid who was raised with privilege and a kid who wasn't. And sort of they end up working in the same place. And it was, it was really interestingly, like, an examination of what it's like when you've sort of been carried around on a red pillow your whole life and when you haven't, and one who has a work ethic and who doesn't. Well, we could not get them to cast anybody. So then we cast the second lead, and then we ended up making it a one-person show. And then we did it as, it's called a presentation, not a pilot, so it's much lower budget. And we made this thing that's 11 minutes long that's complete nonsense. That was the second one. And then the third one was such a complete disaster, every minute, every step of shooting

• 41:13Speaker 00

  that third pilot. And I knew that one wasn't gonna go. And what I learned on that one, when things are going very badly, it's a very nice opportunity to be kind. It's a very nice opportunity to, like, shake everyone's hand, get to know everybody, have a good time. I knew really early on, this is nothing good's gonna come here out of it. Like, we're never gonna, they're never gonna let us make this the way we want to. I learned so much on those, shooting those, getting nowhere close to having them be a television show,

• 41:49Speaker 00

  but learning how to comport yourself, what that process was, how to deal with the disappointments, how to deal with executives and people. Kind of, I remember, you know, so I, this is 20, age 25 to 30. So I was, when I, I stopped writing the pilots when I was 30, partly because I was pregnant and I didn't want to keep writing TV. But I learned, I remember that the producer of one of the pilots came over to me and he said, "You're, you've just been so incredibly poised through this whole disaster." And I thought, "Oh, that's so interesting that, like, I think you think when you're a writer that you're just gonna, like..."

• 42:34Speaker 00

  Your best material is going to win and you're going to fight for your material. And then, of course, we all know that Hollywood's not like that. But you sort of feel like all the stories you hear are about the great material triumph. And at some point, I just realized, you know what? All you can really do is hope for like the best process you humanly can. And I, you know, I learned, again, as we all learn from our failures, the conversation that the world gave back to me on those shows was really to make a television show and to make it good in long term, you're going to have to work pretty much 24 hours a day.

• 43:13Speaker 00

  Because when we were shooting those pilots, I would come home, pee, brush my teeth, maybe take my pants off, lie down on the bed, get up, put my pants back on, brush my teeth, pee, and go back to work. I mean, you barely have time to shower. And the people who were making those TV shows, and that's how they lived. They slept under their desks. They worked 24/7, making 25 episodes of a television show in 1994, 56, which is when I was doing it. Unbelievable work, uh, stress and hours. And I just got married and I was going to have a baby and I was like, I can't do that.

• 43:56Speaker 00

  And I probably could have stayed there and I probably could have gotten on a staff. I really didn't like when I was on staff. I really didn't like that somebody was telling me when I could go home and when I would come back and when I could eat and it's not really a great vibe for me. But that was a conversation with the world where I thought, you know what? I'm 30 and I'm pregnant and, and I'm going to write movies because that's going to be more conducive to my life. So that's another part of the conversation that you have with the world is what am I good at? But also where will I thrive?

• 44:30Elizabeth Day?

  Yes.

• 44:30Speaker 00

  And the Aline, who has not had a chance to take a shower or sleep more than five hours is, is no good.

• 44:37Elizabeth Day?

  I also really appreciate what you say about the process there being the thing, in a way, that I think that is something that failure does teach us, that the journey and not the over-focus on the destination

• 44:50Speaker 00

  Yeah.

• 44:50Elizabeth Day?

  is where you learn the most. I'm aware that we're coming to the end, but there's a piece that you wrote, which is sort of connected to what happened after this, after you acquired all of this knowledge, this process of failure. And then you wrote these hit movies. But then you became a director and a showrunner. And you wrote this terrific piece that even if no one wants to become a director, listening to this, is so relatable for so many women in particular. And it's about having the power to ask.

• 45:22Speaker 00

  Yeah.

• 45:22Elizabeth Day?

  "I regret a few things in my life," you wrote, "but I should have directed sooner. When I think about how challenging it was for me, after a lot of success in the business, to stick my hand up, I think how hard it is when you feel like you're too young, or too female, or too quiet, or too non-white guy, or too lacking a college education or film degree, whatever is preventing others from seeing you as a director." You wrote a tweet about this. "In the tweet, when I say 'men ask,' I'm painting with a crude brush. A finer point on it would be to say, 'There are people who feel entitled to do the job of directing because of their background, or education, or position in the socio-economic hierarchy, or because their parents put all their finger painting

• 46:05Elizabeth Day?

  up on the fridge. And so they ask, and you gotta ask.'" It's so brilliant, that piece.

• 46:12Speaker 00

  Thank you.

• 46:12Elizabeth Day?

  Where did you find the courage, finally, to ask and to show up as the powerhouse that you are now?

• 46:20Speaker 00

  I do think it's a lifelong conversation with the world. My dad believed in me enormously. And then along the way, I had mentors who believed in me enormously. And I'm remiss in not talking about this sooner, but my working with David Frankel on the first movie was just a transformative... Anybody who works with David will tell you, he is the most collaborative, best listener. When we started working, because I'm quite opinionated, and we started, and I did not know him. So I'd never met him, and we were, we had been working together for like, two weeks. And I had talked to him, and I thought, oh, I've been very sassy in this meeting. And I've said, absolutely not, or it must be this, or whatever I said. And I sent him an email.

• 47:06Speaker 00

  And I said, you know, if I'm ever too brassy or too opinionated, just let me know and I can be adjusted at will. And he said, you strike me as someone who is adaptable, honest, hardworking, hilarious, intelligent, whatever he said, this long list of wonderful qualities. And he said, whatever you got, keep it turned up to 11. And many people had said to me, you should direct, but I, when I moved to CAA, they sort of said to me, what do you want? Like, is there anything about being at CAA that would interest you? And I said, I want to meet Nora Ephron. I never met her. And I said, can I meet Nora Ephron?

• 47:48Speaker 00

  And so my agent called her and said, this writer is going to be in New York. Will you sit down with her? And I went to meet Nora Ephron and she had picked up a bunch of gluten free pastries for us to taste. And over the course of our conversation, she was slicing them up and tasting them and saying, well, that's terrible. And that's also terrible. But I said to her, you know, I want to direct, but I don't know as a woman and my opinions and this. And I don't know that much about film technology and cameras and lenses, da, da, da. And she looked at me and she said, um, sounds to me like you just want a bunch of excuses not to direct. If you don't think you can direct, don't. But if you want to, just go and do it. And I thought, yeah, okay.

• 48:31Speaker 00

  And it was so bracing. She didn't baby me at all. She didn't even acknowledge that it was an anything. She said, you sound like you're, you know, it sounded like, and this is a thing people often do. I wasn't really expressing a fear. I was expressing a wish and I wasn't giving myself permission. And she said, so if you, if you want to complain about it, then don't do it. But just if you want to do it, go do it. And it was really, it's the only time I ever met her. She passed away maybe a year after that. And um, yeah, sometimes you need someone to say, just, just go and do it. And honestly, anything that I thought was.

• 49:13Speaker 00

  An impediment or an issue just wasn't. And I do wish, you know, I often say to young women, I wish I had entitlement pills. And I would love to hand them out to young women because just to circle back to our conversation about smallification, I do think we do still a very thorough job of telling women to apologize to the furniture. And I see boys come in to meet with me and they do occupy the whole, the entire piece of furniture and they tell me their hopes and dreams and they say, when can I be the boss? And, you know, it's a gross generalization, but it is really true that we just don't give women the language to do that. So I

• 49:54Speaker 00

  try to do that, you know, go raise your hand and ask for what you want. And you may not get it, but learning to withstand, learning to be amused by failure, which I'm highly amused by failure, learning to walk into walls, learning to withstand a no or any kind of rejection is so key and so critical. And I wish we would teach that more, especially to young women.

• 50:24Elizabeth Day?

  What an empowering and brilliant note to end on, that idea of a wish also being fear, like repackaging fear as a dream, a signal towards your dream. And that bracing advice that she gave you and the bracing advice that you're passing on, I very much enjoyed my hour at the Brosh McCann of finishing school. I cannot thank you enough for coming on How to Fail.

• 50:46Speaker 00

  Thank you. I appreciate it.

• 50:51Elizabeth Day?

  Please do follow How to Fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.