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

Summary

Podcast Summary: How To Fail With Elizabeth Day

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

Original Air Date: May 6, 2026
Host: Elizabeth Day

Episode Overview

This episode of How To Fail features Aline Brosh McKenna—screenwriter, director, showrunner, and the creative mind behind iconic films like The Devil Wears Prada, 27 Dresses, and Morning Glory, as well as co-creator of Crazy Ex-Girlfriend. Elizabeth Day leads a rich conversation celebrating Brosh McKenna’s unique approach to storytelling, her deep understanding of female experience, and—true to the podcast’s theme—her formative failures. Aline shares her three chosen “failures,” how they ultimately led to her greatest successes, and the lessons she hopes creatives, particularly women, can learn from her career journey.

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Key Discussion Points and Insights

Early Inspirations & Shaping a Writer's Voice

[04:20-07:31]

• Origins of 27 Dresses:
  • Inspired by her best friend who was a serial bridesmaid, Aline explores people-pleasing in women. She notes how male executives saw the trait as weakness, but she views it as strength.
    “I think that ability that women have to understand intuitively what needs to be done in a moment is a strength.” (Aline, 04:55)
• Upbringing and Perspective:
  • Raised in an outspoken, immigrant family, Aline wasn’t socialized into female "smallification.” This outsider lens allowed her to critically observe American gender norms.
    “I wasn’t taught to sort of smallify myself by my mother. And that’s maybe one of her greatest gifts.” (Aline, 07:14)

Writing Strong Female Characters & Permission to Be Bold

[07:31-09:13]

• Writing as Empowerment:
  • Both Elizabeth and Aline discuss how writing bold or “bombastic” characters allows for self-empowerment and wish fulfillment. "No one gives you more permission to speak your mind than Miranda Priestly." (Aline, 08:12)
• Balancing Kindness and Assertiveness:
  • Aline values the “typically female” acts of kindness in the workplace, but also relishes writing forthright characters like Miranda Priestly and Harrison Ford’s anchorman in Morning Glory.

The Devil Wears Prada's Enduring Appeal and the Sequel

[09:13-13:34]

• Reflecting on Success at 38:
  • Aline felt “ancient” at the release of Prada, but now sees that as self-critical.
    “Now, of course, I look at 38 year olds, and they seem like little babies to me.” (Aline, 09:51)
• Change and Relevance:
  • The sequel explores how industries like fashion and publishing have radically transformed, making the characters’ journeys newly resonant.
• Sequel Insights:
  • Aline confirms that Miranda’s forgetfulness of Andy is true to real life workplace dynamics: “The idea of the first movie was always that your boss is really interesting to you and you are not as interesting to them.” (Aline, 12:44)

Failure #1: Not Talented Enough to Be an Actor or Singer

[13:34-18:28]

• Importance of Aptitude Recognition:
  • Early failures on stage and in auditions taught Aline about the necessity of aligning aptitude with ambition. "I think sometimes when people get into trouble, it's because they hold on to dreams that are not related to their aptitudes.” (Aline, 17:43)
• Transition to Directing:
  • Realized that her joy lay in storytelling and directing rather than performing.
• Sustained Wonder for Actors:
  • Never lost her awe for actors’ craft, especially when writing for talents like Meryl Streep, Rachel Bloom, and Harrison Ford.

The Creative Process: Collaboration, Preparation & Iconic Scenes

[20:31-25:26]

• Actors' Work Styles:
  • Adapts her approach to suit each actor’s process—some want deep discussion, others none at all. “I don't have rules ever as a director or producer... I love sort of finding the artist where they are.” (Aline, 21:00)
• Memorable Set Anecdotes:
  • Running in new jokes for Emily Blunt; high praise for Stanley Tucci’s collaborative spirit.
• Birth of the “Cerulean” Speech:
  • Written at a Starbucks, built line by line with feedback from Meryl. Aline shares the scrappy, iterative nature of crafting such a now-legendary moment.
    “The minute we cast Meryl, I thought, oh, this could be awesome.” (Aline, 27:59)

The Realities of Writing as a Woman & Comedy’s Value

[29:46-38:17]

• Failure #2: Couldn’t Crack Magazine Writing:
  • Recounts hitting a wall trying to enter elite New York magazine circles, ultimately finding her best fit in screenwriting when encouraged by a teacher.
    “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.’” (Aline, 31:56)
• Comedy and Recognition:
  • Elizabeth calls out the industry’s lack of recognition for female comedies (Prada wasn’t Oscar-nominated, but Borat was). Aline is unfazed by awards, taking more pride in the material and process than external validation.
    “The only thing I ever worked on that I thought, give us the awards, was when I worked with…Well, I knew Meryl was gonna get nominated.” (Aline, 37:33)

Failure #3: Nine Unmade TV Pilots

[39:54-46:05]

• Learning from “Feather-in-Your-Cap” Flops:
  • Working with writer Jeff Kahn, she sold and shot several pilots in her 20s, none of which made it to air. Gained invaluable insights into television production, teamwork, and coping with disappointment.
    “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.” (Aline, 42:38)
• Process Over Outcome:
  • Learned that making long-running TV requires an unsustainable work-life balance for her, leading her to focus on writing movies—work that fit her life and skill set.

Asking for What You Want & The Power of Entitlement

[46:05-51:52]

• Directing as Self-Permission:
  • Regrets not directing sooner, describes the challenge of asking for opportunity as a woman, and the encouragement received from industry figures like David Frankel and a bracing one-off with Nora Ephron.
    Nora Ephron’s advice: “If you want to complain about it, then don’t do it, but just if you want to do it, go do it.” (Aline, 48:29)
• Message to Women:
  • Stresses the importance of resilience and the need to “ask” and withstand rejection, especially for women being socialized to please. “I wish I had entitlement pills. And I would love to hand them out to young women…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...is so key and so critical.” (Aline, 50:45)

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Notable Quotes & Memorable Moments (with Timestamps)

• “It doesn’t take a genius to figure this out. The minute we cast Meryl, I thought, oh, this could be awesome.”
  —Aline Brosh McKenna [00:00] / [27:59]
• “I wasn’t taught to smallify myself by my mother…and that's maybe one of her greatest gifts.”
  —Aline Brosh McKenna [07:14]
• “No one gives you more permission to speak your mind than Miranda Priestly.”
  —Aline Brosh McKenna [08:12]
• “The idea of the first movie was always that your boss is really interesting to you and you are not as interesting to them.”
  —Aline Brosh McKenna [12:44]
• “I think sometimes when people get into trouble, it's because they hold on to dreams that are not related to their aptitudes.”
  —Aline Brosh McKenna [17:43]
• “I sent him an email and I said, you know, if I'm ever too brassy or too opinionated, just let me know…He said, whatever you got, keep it. Turned up to 11.”
  —Aline Brosh McKenna [48:01]
• “Nora Ephron…looked at me and said, 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.”
  —Aline Brosh McKenna [48:29]
• “Learning to be amused by failure, learning to walk into walls, learning to withstand a no, or any kind of rejection is so key and so critical.”
  —Aline Brosh McKenna [51:23]

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Episode Structure & Timestamps

• Intro & Guest Background: [01:45–04:03]
• On 27 Dresses, People-Pleasing & Upbringing: [04:20–09:13]
• The Devil Wears Prada Legacy & Sequel: [09:13–13:34]
• Failure #1: Performing Arts Shortcomings: [13:34–18:28]
• Actors’ Processes & Iconic Scenes: [20:31–25:26]
• The Cerulean Monologue Backstory: [25:26–29:46]
• Failure #2: Magazine Writing Obstacles: [29:46–35:21]
• Comedy Credentials / Awards Recognition: [35:21–38:17]
• Failure #3: Unmade TV Pilots & Lessons: [39:54–46:05]
• Directing, Mentors, and Asking for the Job: [46:05–51:52]
• Closing Reflections: [51:52–52:13]

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Key Takeaways

• Failures are often signals for true aptitudes and resilient growth.
• The best creative work can be forged in imperfect conditions—scrappiness can equal greatness.
• Women need to be encouraged to ask, to claim space, and to withstand rejection without apology.
• Behind every iconic scene is a collaborative process, adaptability, and tenacity.
• Success comes not from avoiding failure, but from leveraging it as insight and motivation.

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For more on Aline Brosh McKenna, revisit her films and look out for the much-anticipated Devil Wears Prada sequel. For those chasing creative dreams (and weathering failure), her journey is a beacon.

Transcript

[Aline Brosh McKenna]

It doesn't take a genius to figure this out. The minute we cast Meryl, I thought, oh, this could be awesome. 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.

[Elizabeth Day]

Welcome to how to Fail, the podcast that believes that sometimes the message is in the mess. Before we get into conversation, please do remember to, like, subscribe and follow so that you never miss a single episode. In 1987, a newborn baby is abandoned in a remote spot. Nobody goes down that lane. Why would you think anyone would have picked me up from there? For decades, Jess has searched for answers. Why didn't that person want me? But as she gets closer to the truth, things spiral out of her control.

[Aline Brosh McKenna]

I think I'll always be angry. Could it have ended differently?

[Elizabeth Day]

From Tortoise Investigators and the observer, this is foundling. Lies always come out, don't they? Skeletons are always going to come out eventually. Listen Wherever you get your podcasts, it's

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[Elizabeth Day]

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 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 Hegel singing drunkenly to ELTON John in 27 dresses. Or it's Stanny Tucci 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. 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, 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 show ran 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.

[Aline Brosh McKenna]

2.

[Elizabeth 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. Being funny, Brosh 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. Aline, Rosh McKenna, welcome to how to Fail.

[Aline Brosh McKenna]

Thank you. Everybody. Always like quells after your introductions and I feel all tingly.

[Elizabeth Day]

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

[Aline Brosh McKenna]

Thank you.

[Elizabeth Day]

Thank you for all of the work that you put out into the world. Thank you. It really has meant so much to so many of us and I know we're gonna talk about the Devil Wears Prada, obviously, but 27 dresses was such a great movie.

[Aline Brosh McKenna]

Thank you. I wrote that it was inspired by my best friend, had been in about 12 or 13 Wed 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. But I think that ability that women have to sort of shape shift and understand intuitively what needs to be done in a moment 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?

[Elizabeth Day]

So interesting. Have you had your people pleasing years?

[Aline Brosh McKenna]

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 and 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 grande dame, 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 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 great. And they always encouraged both my brother and I to be very outspoken. And so I'm fascinated anthropologically with the sort of apologies and the abnegation 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 when I work with younger female writers and I'll hear them saying, well, this is probably terrible and we don't want to do this, not this, but this is not what we want to do. But maybe. And I had a crazy idea and a bad idea and their legs are cinched together much like ours are to sort of occupy the least amount of space on a chair. And then boys are really encouraged to splay in every way imaginable. And I wasn't taught to sort of smallify myself by my mother. And that's maybe one of her greatest

[Elizabeth Day]

gifts, that idea of women littering their ideas, their emails, their communication with mitigating words. 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. And I realized that if this bombastic, unscrupulous billionaire man, then it was within me to lean into that. And so I set myself this challenge of acting 5% more like that character. Have you found that writing characters has helped you develop well, I mean, no

[Aline Brosh McKenna]

one gives you more permission to speak your mind than Miranda Priestly. So that was. I always love 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 characters, Miranda Priestley. And then I wrote a movie called Morning Glory with Harrison Ford playing a 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.

[Elizabeth 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 woman.

[Aline Brosh McKenna]

Well, I thought I was ancient. I mean, I felt very ashamed that my first hit. 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 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 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 just changing all around you and obviously happening in the movie business, but kind of everywhere, you know. Cause 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. Managing a downturn so, you know, it's as fun a movie as you can make about managing downturns, I think. And was that the pitch? Yeah.

[Elizabeth 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 where you're like, am I funny anymore?

[Aline Brosh McKenna]

To get the band back together? So it started with me over the years. Cause 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 Meryl 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 Meryl and Stan, and we were able to sort of talk about, you know, what was relevant and where these folks were, and it felt like it made sense.

[Elizabeth Day]

You probably can't tell us anything, but can you tell us anything about where the Devil Wears Prada Patu meets all of these legendary characters?

[Aline Brosh McKenna]

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. Does she have dementia? And I'm exactly the same age that Miranda Priestley 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 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 your boss is really interesting to you and you are not as interesting to them.

[Elizabeth Day]

Yes.

[Aline Brosh McKenna]

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 and set that all up again.

[Elizabeth 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.

[Aline Brosh McKenna]

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 in 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 I. 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 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 sang at my graduation, which was 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 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 audition for all the plays at the same time. And then I went there the day that all the cast lists were posted, and there was, you know, 50 cast lists, which is a good amount. And there was another kid who was in, 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 Lightboard 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. 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 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 been true. I mean, just imagine writing lines for Harrison Ford, you know, just, yeah, well, Meryl Streep. 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? And she goes, that was so bad. 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.

[Elizabeth Day]

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[Aline Brosh McKenna]

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[Elizabeth 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 almost. Is there another thing that links Meryl Streep, Harrison Ford, Rachel Bloom, Stanley Tucci that you can now see? Oh, that's. That's how they prepare. That's what makes them different.

[Aline Brosh McKenna]

You know, they're. 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, We Bought a Zoo. That movie is called you'd Place or mine. It's a Netflix movie 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 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, exhausted, wants to send me a six page email after a run through, great. 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.

[Elizabeth Day]

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

[Aline Brosh McKenna]

I just was remembering that like Reese has a different. I would go to Rhys and 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. And she also likes to do a scene in the moment right as you're about to do it, and then talk to me. And so that was interesting. Cause 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 Rhys 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 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 doing it. And I mean, I could go on and on about. I'm so fascinated, pleased about how brilliant they are, 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. Cause 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.

[Elizabeth Day]

Does that just mean you're throwing it at the.

[Aline Brosh McKenna]

I'll just come in and say, what about this? 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 Andy, you deign to work here. And I remember I said to Stanley, do you want me to make any adjustments or change anything for you? And he said, no, I'm good. And that was, like, 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 go through every scene. And then in both Prada movies, Annie is in almost every scene and has to carry 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 so much work for one person. It's so much through the scrim of her perception.

[Elizabeth Day]

Before we get onto 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 much many of us and is so beautifully done. Can you tell us about how that came about?

[Aline Brosh McKenna]

Meryl had looked at 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. And then 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 it was on the 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. So, for instance, I said I'd written in the section about blue. I sent a list to him that said lapis, azure, cerulean. And she picked cerulean. She said, great. 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, knowing how movies are and 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 knowing that it was going. Pinging for Meryl back to me and getting her feedback. And then I sent it back and said, you know, here's this big chunk. I don't know, you can cut it down. You 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 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? Maybe could you improve this or you could improve 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 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 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 it was fun and great, and I loved writing the script and I loved working with David. But, you know, 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 started 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.

[Elizabeth 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 your second failure is. Is your failure to be a magazine writer after you graduated college. So tell us about this.

[Aline Brosh McKenna]

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 magna cum laude. Magna cum laude indeed. And not summa, though, importantly.

[Elizabeth Day]

Oh, is that above?

[Aline Brosh McKenna]

Summa's above. And my father was furious because one of the girls I went to second grade with was summa, 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 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. 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 at 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. 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. 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. 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 fruitless it was. No one liked our ideas, no one wanted to meet us, no one wanted to invite us to a party. And then when I started screenwriting, it was like, oh, I gave the script. Oh, I'd like to be your agent. You're gonna get a blind deal at Universal. I started to just squinge some doors open so I felt like I had been Andy. And in the beginning of the movie where she sort of offered like, oh. Cause I also tried to temp. That was Also a disaster. Oh, my God, disaster. But when I got the book, I thought, oh, I understand her. I think we all go from being Andy's to Miranda's over time. Get much more crankier when we get the wrong coffee order.

[Elizabeth Day]

Everything that you say, I am relating to extremely deeply for reasons that 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. To see people as they are from the position of observer. But also the other part of your gift is the ability to draw humor from that.

[Aline Brosh McKenna]

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 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 onto the phrase I'll catch you later at some point. And that's what would happen, is my parents would latch onto a phrase of 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, Eileen, I will catch you later. And all of my friends said that. But you get very tuned to rhythms of speech when you are in a house where people are searching for words,

[Elizabeth Day]

searching to fit in, searching for the key to the code. Before we get onto your final failure, 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 at least, that you were not nominated for an Oscar for Devil Wears Prada. But Borat was.

[Aline Brosh McKenna]

Well, I was dumb. I didn't get any help. I was very afraid, and I did not know what I will say that the baftas were the same night as the Writers Guild Awards. And I was like, gee, do I go to the baftas and mingle with these, the most fabulous people that I've worshiped 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 Baptist, because I had friends in the improv group, because I know people out here who really do comedy comedy. 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 standup. 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 the bad version is, like, drama with jokes. I don't fetishize comedy cred the way a lot of comedy people do. And that started in college at the Lampoon. So I wrote a funny column for the. 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.

[Elizabeth Day]

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

[Aline Brosh McKenna]

No, I don't. 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 gonna 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, thwapped him off the. I was like, oh, my God, there's Miranda Priestley. And I. After that take, I said to him, I mean, she's gonna get nominated. I. I knew that.

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[Elizabeth Day]

Ever wondered why some trends are just suddenly everywhere? Newsflash. Nothing. Nothing gets popular by accident. I'm Brittany Luce, and on the It's Been a Minute podcast, I take the things you and I are both obsessing over and show you the invisible forces behind the scenes that make us love it or hate it. Be smarter about what you're consuming. Listen to the It's Been a Minute podcast today. Your final failure is Co writing nine TV pilots in the 90s and never getting any on the air.

[Aline Brosh McKenna]

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 Kahn, 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. 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 rode 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. We wrote one, it got shot, but it was the 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 plant has been off. It's very boring. I can but 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 L. That's interesting. They cut up carrots for lunch. 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 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 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 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 that third pilot, it. And I knew that one wasn't going to 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 going to come here out of it. Like we're never going to. They're never going to 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, but learning

[Elizabeth Day]

how

[Aline Brosh McKenna]

to comport yourself, what that process was, how to deal with the disappointments, how to deal with executives and people kind. I remember, you know, so this is 20, age 25 to 30. So I was, when 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 remember that the producer of one of the pilots came over to me and he said, 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, your best material's gonna win and you're gonna fight for your material. And then, of course, we all know that Hollywood's not like that, but, you know, 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 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. 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 in the night, that's how they lived. They slept under their desks. They worked 24 7, making 25 episodes of a television show in 1994. Five, six, which is when I was doing it. Unbelievable work stress and hours. And I'd just gotten married and I was gonna have a baby, and I was like, I can't do that. 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 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? And the Ilene who has not had a chance to take a shower or sleep more than five hours is no good.

[Elizabeth 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 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 through 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. Yeah, I regret a few things in my life he 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 socioeconomic hierarchy or because their parents put all their finger painting up on the fridge. And so they ask, and you gotta ask. It's so brilliant, that piece.

[Aline Brosh McKenna]

Thank you.

[Elizabeth Day]

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

[Aline Brosh McKenna]

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 I did not know him, so I'd never met him. And 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 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 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? And so my agent called her and said, this writer's 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 tasting 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. And she looked at me and she said, 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. 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 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 yeah, sometimes you need someone to say, just go and do it. And honestly, anything that I thought was 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 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, especially to young women.

[Elizabeth Day]

What an empowering and brilliant 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 McKenna Finishing School. I cannot thank you enough for coming

[Aline Brosh McKenna]

on how to Fail. Thank you, thank you. I appreciate it.

[Elizabeth 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 podcast podcasts. Please tell all your friends this is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.

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