How To Fail With Elizabeth Day - Aline Brosh McKenna - The Rom Com Queen Who Wrote The Devil Wears Prada
Episode Date: May 6, 2026Aline 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 Th...e 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 podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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It doesn't take a genius to figure this out.
The minute we cast Merrill, 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 L.A. 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.
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
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From Tortors Investigates and the Observer, this is foundling.
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This is a commercial message brought to you by Gofundme. 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 Hagle singing drunkenly to Elton John in 27 dresses.
Or it's Stanley 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 L.A.
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 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 2.
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.
Thank you.
Everybody always like quails after your introductions and I feel all tingly.
Oh, well, it is such an honor to meet you.
Thank you.
Thank you for all of the work that you 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 west bridal,
obviously, but 27 dresses was such a great movie.
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. Wow. But I think
that that ability that women have to sort of shape-shift and understand into the fact that,
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? So interesting. Have you had your people pleasing
years? You know, it's funny. That's the one that is the least like me in 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'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, it was a strange sitcom. But I wasn't socialized in girls
having to please others. My mother was a grand dom, 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. It 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 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 rassy. 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 don't want to do this, not this, but, you know,
this is this is not what we want to do, but, but maybe and I had a crazy idea and a bad idea.
And their legs are cinch 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 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 I could imagine this bombastic, unscrupulous billionaire man,
then it was within me to lean into that.
Right.
And so I set myself this challenge of acting 5% more like that character.
Have you found that writing characters has helped you develop as a person?
Well, I mean, no one gives you more permission to speak your mind than Miranda Priestley.
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-care merit, 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.
The Devil Wears Prada, I refuse to believe it's 20 years.
since that movie came out.
But apparently it is.
Yeah.
That's what the chronology of time tells me.
You were 38 when that movie came out.
Yeah.
So 20 years on now, I'm just really interested in how different you feel as a...
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 first big,
first big successful thing. And I kept thinking, my God, 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
t'was 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, having in,
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 downturns, I think. And was that the pitch? Yeah. 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
when you're asking what you're like, am I funny anymore? 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 we're 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, and Merrill and
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.
You probably can't tell us anything, but can you tell us anything about where the devil wears part of two meets all of these legendary characters?
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 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, 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
your boss is really interesting to you and you are not.
is interesting to them. Yes. 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 set that all up again. Well, what a privilege?
and 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. 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 in 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 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 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 is 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 or 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
audition 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.
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 marshalling 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 is 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's been true.
I mean, just imagine writing lines for Harrison Ford, you know, just.
Yeah, well, right.
Street. And then imagine writing, you know, lines for Merrill Street 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 a,
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.
Oh, please.
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.
Yes, that's so well put.
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I'm Craig Melvin. Cheers. Cheers. Cheers. I've always been a glass, half-full kind of guy. And now,
I'm talking to some people who look at the world that way too. Some really fascinating folks who share their defining moments.
their triumphs, their challenges.
Their stories are funny and quite candid.
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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.
Yeah.
Is there another thing that links Meryl Street?
Harrison Ford, Rachel Bloom, Stanley Tucci, that you can now see, oh, that's how they
prepare. That's what makes them different. 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 Coochard in a movie. And we bought a zoo. That movie is called Your Place or Mine.
It's a Netflix movie.
a romantic comedy, but I did also work on Weebaught 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 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.
So were Reese and Ashton different?
Is that why you mention them in this context?
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,
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 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 to her and we looked at it and then we did that. And then with Rachel, you know, Rachel was,
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, fine, got it, doing it.
And I mean, I could go on and on about 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 tick.
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.
Does that just mean you're throwing it in from the side?
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, nope, I'm good.
And that was like as meaningful of 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 so much work for one person.
It's so much through the scrim of her perception.
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 merrill 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
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 merrill 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 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 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 Merrill and then getting notes from Merrill and then conveying them to me. So for instance,
I said, had written in the section about blue, I sent a list to him that said,
Lapis, Azure, Cirulian.
And she picked Cerulian.
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, 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 Merrill back to me and getting her feedback.
And then I've 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, 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 L.A.
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 Girdier 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 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.
And he 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. But I was, I had, I mean,
it doesn't take a genius to figure this out. The minute we cast Merrill, 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, I, the second week cast Merrill, I remember I was so astonished
when David told me that I sat down on the sidewalk and Larchmont and start crying, because
I was like, oh, there's a big wave coming and I got to 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.
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 unpressuous 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 matcher.
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 your failure to be
a magazine writer after you graduated to college. So tell us about this. Absolutely. 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 come loudly. Indeed. And
not Summa though, importantly. Oh, is that above? 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
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
and Halloween.
She really 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 whole 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. In 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 L.A. And I thought, well, take a screenwriting class. I'll start with.
the thing I loved 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 L.A. 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 L.A. and then bang 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.
Like, 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 know, you're going to 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.
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 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.
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 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.
Yeah, you also, you develop, I think, a lot of,
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, Aline,
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.
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, Helene,
that you were not nominated for an Oscar for Devil Wears Prada,
but Borat was.
Well, I was dumb.
I didn't get any help.
I was very afraid and I did not know what I.
I will say that the BFTAs were the same night as the Writers Guild Awards.
And I was like, gee, do I go to the Bafters 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 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 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 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 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-headed comedy.
The things that I have always found funny are things that.
that come from emotion and heart and soul and embarrassment
and like really immediate human experiences.
But do you think you should have won more awards?
Because I do.
No, 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 Merrill 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 going to get nominated. I knew that.
Your final failure is co-writing nine TV pilots in the 90s and never getting any on the air.
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 a planted spin-off of
another show. And it was the first time, so the first time I ever wrote anything that got shot was that
a plant had spinoff. It's very boring. I can, but 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.
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 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 that third pilot. 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 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 this is 20, age 25 to 30.
So 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 going to like,
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
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 are making those TV shows
and that's how they lived.
They slept under the desks.
They worked 24-7, making 25 episodes of a television show in 1994-5-6,
which is when I was doing it.
Unbelievable work 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.
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?
Yes.
And the elene who has not had a chance to take a shower or sleep more than five.
five hours is no good.
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
overfocus 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 required all of this knowledge to 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, 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 socioeconomic.
economic hierarchy or because their parents put all their finger painting up on the fridge.
And so they ask and you got to ask.
It's so brilliant that piece.
Thank you.
Where did you find the courage finally to ask and to show up as the powerhouse that you are now?
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 and 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 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?
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 Nor 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.
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 young women.
What an empowering and brilliant note to end on.
That idea of a wish also being fear.
Repackaging fear is 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 on How to Fail.
Thank you. I appreciate it.
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.
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