WHAT WENT WRONG - The Devil Wears Prada (with Jameela Jamil)

Episode Date: April 27, 2026

When director David Frankel signed on to adapt the novel The Devil Wears Prada into a movie, he didn’t realize he’d be up against the real Miranda Priestly herself: Anna Wintour. This week Chris, Lizzie, and very special guest Jameela Jamil discover how it took 5 tries to find the right screenwriter, why Anne Hathaway was the 9th choice to play Andy Sachs, and how fear of retribution from Anna Wintour almost shut the whole thing down. Find out why Meryl Streep went method with her role, how Emily Blunt totally transformed her character, and why a scandal brewing in Anne Hathaway’s personal life bled over onto set. Hosted on Acast. See acast.com/privacy for more information.

Hello, dear listeners, and welcome back to another episode of What Went Wrong, your favorite podcast, Full Stop, that just so happens to be about movies, and how it's nearly impossible to make them, let alone a good one, let alone, the movie that Damien Chiselle saw and said, Not My Tempo. We're talking about the original Whiplash, The Devil Wears Prada, one of my favorite e-watches. As always, I'm Chris Winterbauer, joined by Lizzie Bassett. And Lizzie, who else do we have here today?

We have an unbelievably special guest for this episode. I am so excited to talk to her about this. We have actor, writer, advocate, music producer, what can't she do? And host of the podcast Wrong Turns, which I really, really love. It's Jamila Jamil. Thank you so much for being here and welcome. Hello, thank you for having me. I love films, so I'm always excited to talk about them.

Well, I think this one is a particularly good fit for several reasons that I can't wait to dive into, but I also just want to say, I really love your podcast so much. You're a very generous host, which I feel like is a rare thing, and you're so funny, but you also just like really clearly make the guests so comfortable, and it's very lovely. So go listen to Wrong Turns with Jamila Jamil if you have not yet. Oh, thank you. And if anyone wants to come see me live in L.A., I'm doing my first ever Netflix as a joke festival, which is very intimidating as a non-comedian to enter a full-on comedian's festival.

but I will have with me, Lamon Morris, the Winston from the New Girl, and I will have Leisa Trager and Chris Fleming, the man of the moment as my guest. Oh my God! So I'm very excited,

so the tickets are available now, but anyway, if anyone wants to come see it live, it's so much crazy alive, even than in the room. That sounds wonderful. All right, well, so let's just dive right in. How we usually start this is,

I will ask both of you, and I'll start with you, Jamila, if that's all right. Had you ever seen, the Delaware's Prada before. And what was your experience on watching it more recently, let's say? I have loved that movie since it first came out. I went and saw it in a cinema and loved it so much that I waited till the next showing

to watch it all over again because it was such a feast for my little eyes. You know, I think I was much younger. What year did it come out? 2006. Yeah, 2006, right. So I was, I think, barely 20. and I just started working in the fashion industry, so I was really just like soaking it all up.

And then it became, even though it is deeply problematic in many ways, it became a sort of comfort rewatch, and I will watch it on any flight if it's available, and I watch it when I'm sick. It's a go-to. I watched it twice over the course of the pandemic. I love showing it to other people. So I think I've seen it probably upwards of 25 times.

Which is ridiculous. I think it's probably the movie I've watched the most in the world, apart from maybe the Truman Show. Oh, wow. Interesting. Good picks. Chris, what about you? 2006, I was also getting started in the fashion industry.

But I saw it in 2006, and I was a Anne-Hathaway fan because I secretly loved The Princess Diaries. I have two sisters, and we saw that in theaters. And it was great then, and it remains great now. Like you said, it's a time capsule of 2006. Certain lines, you go, oh, oh, oh, wow. You know, and I watched the September issue, the documentary about Anna Wintour and the making of the 2007, I think, September issue. Well, is it about Anna Wintor?

No, it's really about Grace Cottington. Yeah, who's far more interesting. She is. But it's such, like you said, it's a warm blanket movie. It's so snappy and breezy. With the exception, I would say, of any time we go back to her boyfriend and friends, the movie kind of grinds to a halt. But any time that Merrill Streep, Stanley Tucci, Anne Hathaway. Simon Baker is written as such an asshole, but he's so.

charming that you kind of just want her to leave Adrian Grenier and just take the Yarlsburg and go. And let's go with this creepy older dude. But again, it's like weird peak girl boss feminism in some ways. It's like Lindy West's new memoir just came out and there are all these articles about the death of millennial feminism. So I thought it was interesting that we're covering this movie right now. But I stand by The Devil Wars Prada. It is a great rewatch. And it's a very fun movie. And we'll talk about all the problematic parts in a bit. Yeah, I agree. So same as everybody here. I saw this in theaters. I was, I think, 16 years old when this came out. And watching it again for the podcast, I did not realize how much this shaped my psyche as a teenager. And we're going to get into this.

You know, we keep referencing there are problematic parts of this. The way that the movie deals with Andy's weight is something that... Psychotic. And illegal, it feels almost. I know. And it's something I wrestle with every time I watch this movie. But then in researching it, I don't know. It's more complicated than I realized. It's very true to the time. Like I was working in the industry. That's what it was like. It would be disingenuous for them to have said or written anything else. And we were, we were still in the throes of size zero. Yes. So. Yes. That line of like, you know, wake up six, it's literally burned in my head. Like I remember thinking like, oh, you know, six isn't good enough. I'm a size eight. Like it's, you know, it, well, then, not anymore. I've had a baby. But, you know,

It's like, I didn't understand how much this movie had shaped my perception of what a female body is supposed to look like for better and for worse. That being said, I love this movie. I think that this is an incredible adaptation as we're going to get into. I'm almost done with the book that it's based on. And they really do a bang up job of making this such a tight, funny movie. I love all of the performances. I'm with you, Chris. I think kind of through no fault of his own. I'm not crazy about Adrian Grenier. in this movie. I've always been team Simon Baker. It's just not the most interesting part. He's the villain! Yeah. He's the fucking villain.

And I think that's the craziest thing to me. I think one of the reasons I rewatch it now as an adult is because I'm so happy for my lens to have shifted to understand A, that Andy is not fat at the start of the movie. No, my God. She's not better at the end of the movie, because that is what I believed when I was 19 or 20 when I first watched it. Yeah.

And then I have understood that Meryl Streep's character, whilst being a villain of sorts is not the villain. It's clearly fucking Adrian Grenier. And I remember being such a young pick-me asshole that I was like, I can't believe she's not hanging out with her gorgeous boyfriend. And now when I re-watch it, I'm like, he's a fucking cunt who doesn't support her friends and fuck her friends.

I agree with you, fuck her friends. Who have no empathy for her whatsoever, that moment where they're throwing her phone all around. I would be so mad. I would torch them all. I would set fire to that fucking table over that moment. I agree. But he is so self-absorbed, and the idea that she's going to now move, like, quit her job, whether or not her job was toxic, quit her life and her trajectory to move to whatever fucking fucking town he's fucking moving to where he's going to still make her grilled cheese sandwiches.

Which look burned, by the way. It's propaganda. Like, ultimately, all of Hollywood in that era was propaganda about the crumbs that women should tolerate. I agree. I think that the changes that they made to that character for the movie are interesting because he is. very different in the book. Oh, interesting. He is not a villain in the book at all. He's like kind of a saint. And actually, Andy's a bit more of an asshole, which I almost liked a little bit better, but we'll get into all the differences between the book and the movie. Let's go ahead and

dive in. So we always start with the details. The Delaware's Prada is directed by David Frankel. It was produced by Wendy Finerman, who came up in our Forrest Gump episode. She's a badass, especially when it comes to adapting literature. Screenplay by Eileen Brosh-McKennanah, based on the best-selling novel by Lauren Weisberger. And of course, it stars Merrill Streep, Anne Hathaway, Stanley Tucci, Simon Baker, Emily Blunt, and Adrian Grunier. It was released June 30th, 2006, and as always, the IMDB logline is, with an aspiration to become a journalist, Andy, a smart but sensible young graduate travels to New York. She starts working as an assistant to one of the city's biggest high-fashioned magazine editors, The Cynical Miranda Priestley.

Smart but sensible. That's an interesting logline IMDP. She's not too smart. They want to make it clear. She's not too smart for her own good. She's sensible. She's sensible. Is that their nice way of saying she starts as a size six? All right. So let's begin with the real Andy Sachs, which is Lauren Weisberger. Because spoiler alert, if anyone doesn't know, this is a very, very thinly veiled portrayal of Lauren's own time at Vogue. So it's a Roman Aclef. That's what it's called. Roman a clef, yes, that's the term. Yeah. So she grew up in Allentown, Pennsylvania, the daughter of a teacher and a mortgage broker. She was also a real smarty pants who graduated with an English-lit degree from Cornell University. And as many recent college grads are wont to do, she went backpacked around Europe, the Middle East, Southeast Asia, at which point she found herself in need of a job. So she moved to Manhattan, pulled together. What I kept seeing referenced as an impressive cover letter, though I could not find it myself to confirm this. And it caught the eye of HR at Conday Now. and then Bing Bang Boom, she was hired as an assistant to the one and only editor-in-chief of Vogue magazine. Who is? Anybody?

Anna Wintor. Anna Wintor, thank you. Yes. Okay. So, Jamila, as certainly the most fashionable person here, could you maybe explain the impact of Anna Wintor or just like a tiny little bit about who she is? Anna Winter is the editor of American Vogue, but also kind of the leader of Vogue at large globally. Ultimately, I think she has the final say on who. gets hired to be editors of other arms of the publication. She decided who our supermodels were. She was instrumental in all of the designers who are big designers, you know, who've entered

the lexicon of iconic designers, were handpicked by her. She cherry-picked the faces and the tailors and the colours of multiple generations of women. And I think also was committed so heavily to the size zero that I would hold her partially responsive. for the eating disorder culture of 30 years of women. I agree. She was the editor-in-chief of Vogue from 1988 to 2025. But you know what I will say, just quickly, which is problematic of me, is that one thing I've always felt is that how dare all these editors

not physically live up to the terrifying standards they are putting out into the world? She does. And she... She does. Yeah. She is one person who's somehow smaller than all of her own models. So she does walk the walk, not just talk the talk like everyone else. I don't know if that makes it better, but it's comforting to me.

Fair enough. She did finally step back at the age of 75, but she stepped into a new role as the chief content officer for Condé Nast and Global Editorial Director. So I don't know if we can really call that stepping back. But anyway, it quickly became clear that Lauren, who wanted to be a writer, wasn't going to be doing a whole lot of writing. at this job. She was faxing, filing, getting coffee. Now, to be fair, these are all the things that assistants do. We've all done them. I will say in my reading, there's a bit of entitlement in terms of what you think you should be doing at your literal first job out of college, but whatever. But according to another former assistant to Anna Wintor, this is how her assistance duties

actually broke down. So she generally had two or three assistants at any time. And Amy Odell's Anna the biography explained their responsibilities like this. The first assistant managed the other two assistants, and they handled Anna Wintour's schedule. They were her primary point of contact, and this is the only one who got weekends off. The other two assistants, the second assistant, they would deal with caretakers, i.e. nannies, chefs at Wintor's Manhattan and Long Island homes. They would coordinate film screenings, and of course, look after her dogs. And then the third assistant would run errands. They pick up theater tickets. They helped during fashion week. They ordered Anna's clothes directly from designers. Assistant to the regional manager.

as it would be known in the office. Yes, exactly. Now, according to Anna, the biography, every new assistant was given a 21-page instruction manual on how to handle most of their tasks. Workday started at 7 a.m. and often ran at least 12 hours. And former assistant Meredith Aspland revealed her starting salary was $25,000, while another one of Anna's first ever assistants shared that she lost eight pounds in her first two weeks. Both of those things, by the way, do make it into the book. Now, another former assistant revealed the detail we get in both the book and the movie that Wintour would sometimes address her using the other assistant's name. And another one was, of course, told, you must not leave your desk. The desk must not be unmanned at any time.

That woman did say this did not come directly from Anna Wintor. It was more sort of lore that, like, you cannot leave the desk unmanned. I do want to note, this is an unauthorized biography that was made without Anna Wintor's participation, obviously. And Gwyneth Paltrow, who also had an unauthorized biography written by the same author, did say she totally missed everything, the truth of who I am, what my impact is. So, I suppose take all of this with a grain of salt, except that it's pretty much confirmed by her former assistants. Now, Vogue's managing editor at the time, Lori Jones, gave a different reason for why Lauren didn't get to do any writing in her time at Vogue. She said Lauren was, quote, a lovely girl, but not a great writer, poor thing.

So mean. That is such expert fashion shade. It's pretty good. To couch it in kindness is horrific. Yeah. If anybody calls me a poor thing, I'm done. Just take me out. It's an amazing shit sandwich, yeah.

Yeah. So in 2000, after only 10 months on the job, Lauren did The Unthinkable. And she asked Richard Story, who was an editor at Vogue, to take her with him as he was leaving for Departures magazine. He agreed, and she went with him. Now, she did do quite a bit of writing at Departures, but it seems that Story thought she could use some writing lessons. Everybody's like, you're not very good at this. Oh, no. She's like, I already went to Cornell.

He's like, you should go back. Do it again. She went and took a creative writing class at night, and as part of her homework, she began writing about her former job at Vogue, and more specifically, her very high-profile boss. Now, her teacher read this and apparently just saw dollar signs blinking in their eyes because they shared the writing with literary agent Deborah Schneider, whose response to the, at this point, 15 to 20 page just series of anecdotal stories was, if she wants to sell this book, I can sell it this afternoon. And Deborah was correct. She sold the Devil Wars Prada one week later in May of 2002 for a reported $250,000. Wow. Did they have the name already? Because one thing I want to mention,

the name is so good. This is one of the best titles. Of all time. Yeah. It's an amazing title. I think they did. Everybody knows the title. And it's a great poster, too, we should mention. Oh, yeah. Just that iconic shoe on it. But anyway, it's an amazing title. The cover of the book is great, too.

All the marketing around this is really excellent. Yeah. By the way, a little fun fact when Anna Wintour was informed about the book and the fact that the quote-unquote villain, Miranda Priestley, was not so loosely based on her. She reportedly said, I cannot remember who that girl is. Yeah, it's the madman. That's the brand. I don't think about you at all. Honestly, I believe her.

So very shortly after the news of this deal broke, producer Wendy Feinerman, who again, this is the woman who would not give up on Forrest Gump, optioned the film. Now, she had a three-year first look deal with Fox 2000 at this point that began in 1999, so Fox 2000 is where the Devil Wars Prada landed. And when Carla Hacken, then executive VP at Fox 2000, first read Weisberger's manuscript, she said, quote, I thought Miranda Priestley was one of the greatest villains ever. I remember we went aggressively in and scooped it up. But here's the thing. They did not have a finished novel. They had about a hundred pages of a manuscript that were essentially just a setup. According to Feynerman, quote, it was set obviously in the world of fashion and we all knew what it was and we all knew the background of the book. We had to wait five or six months to get the other half of the book. We had no idea what happened with the story, but the setup was so great. So Fox 2000 is like, we're just going to start working on the story anyway, even though they had no idea where the book was going to go because they were like, doesn't really matter. But

In April of 2003, the Devil Wars Prada hit bookshelves and it absolutely blew up. It spent half the year on the New York Times bestsellers list. And I can confirm every teenage girl was reading it, including myself, even though I honestly didn't understand like 90% of what was in it. All the products, the bang and oliphson phones. I didn't know what any of this shit was. Jamila, was this on your radar when the book came out or not until the movie? Not at all. No, no, no.

When I was at school around this time, I was so head in textbooks that I didn't have time to read. anything that wasn't on my curriculum. Oh, good for you. But then I watched the movie and then watched it 25 times and never revisited any of those clever books. Never read a book again. Left school with very few qualifications and fulfilled zero of my potential.

And now if anyone's seen my substack, the grammar would tell you that I've never been to school a day of my life. I refuse to believe that. Well, all you'd have to do is take a creative writing night course, like Lauren. Sure, sure, and I'll write a best seller. Yeah, well.

So despite the book's massive cultural impact, there was one person whose feathers were reportedly not at all ruffled. Any guesses? Who just didn't care at all about this book? Anna Wintour. That's right. Anna Wintour. Of course. Snow Queen Ice Dragon herself. Did she fuck? I've always thought that was horseshit. Like, I think that it rattled her terribly. But she's from a... 100%. You know, there's a very old-school British concept of never complain, never explain, is the kind of royal families. You know, it's a very like British aristocratic position to take so that you never ever have to clarify or not clarify anything. And it's both a very frustrating way to live, but it's also a much more peaceful

way to live because things move on in ambiguity. And there's that expression of like, it's better to be considered a fool than to open your mouth and remove all doubt, which is an extraordinary expression that I love so much. Not the way I live my life, unfortunately. Yeah, I was going to say from three podcasters. No, no, no, no. All I do is remove, I've been removing all doubt for 17 years straight, you know. So that's sort of my, it's my exact brand, I would say, is just removing all doubt at all times. But I think it must have rattled her really badly. But also, Meryl Streep turned her into an icon. And if I may add to that, as I've gotten older, you know, my biggest fear when I was younger is that people would think that I'm

difficult and scary because of the color of my skin and because of how outspoken I am, in spite of the fact that I'm actually a softie, I'm considered intimidating and scary to certain people. And as I've gotten older, I've realized that, oh, that is the sweet spot in life is to be a woman who other people fear because people just leave you the fuck alone. Yeah, good point. And actually, it's more dangerous for them to realize that you're just made of like, I'm like a lint ball. You know, I'm just like putty in the middle. Don't tell them. No, I know.

It's too late. But it's fine. This community can know. But everyone else on the internet, I prefer that they think I'm crazy and scary. And I can see why. There's a power to it. There was a part of her that's like, oh, I sort of win if everyone thinks I'm absolutely terrifying. And so possibly that's also why she never tried to navigate any of this to seem untrue.

Yes. And also, look, she's an incredibly successful woman, and that's something we're going to get into. I think the movie does do a very good job of is it makes her far more complicated than she is on the page in the book. And I do think that that's a good thing at the end of the day. According to William Norwich, who is a former Vogue editor and also a New York Post gossip columnist, he said that she just didn't really see herself as a cultural phenomenon and told friends, I'm so bored by me. What a good statement. Now, since the book was pretty much immediately a runaway hit, Fox is like, all right, we got to find a screenwriter, get this thing going. So first up was Peter Hedges. At this point, best known for writing What's Eating Gilbert Grape and About a Boy. Wow. Yeah, I mean, Gilbert Grape, not an amazing comp. About a Boy, though, I think actually a pretty good comp. for this. And he delivered what everyone seemed to agree was a pretty solid first draft, but he actually

quit the project very quickly because he found it way too overwhelming and did not want to be involved in it. Perhaps he was busy raising future film star Lucas Hedges. I didn't realize that that was his dad until I started researching this, but it is, and they look identical. Next up was Howard Michael Gould, who was mostly a sitcom writer, and then Paul Rudnick, who had written Adams Family Values. A lot of guys that we're getting through here. We're not done with the men. Okay. Rodnick was only available for two weeks. He did a pass just on Miranda Priestley's dialogue.

And then came Don Roos. And yeah, what's the theme amongst these four writers? They're just like, I don't know what's not working. Let's just try some more dudes. Let's hire more men, men, men, men. Yeah, that is so bizarre to me. Like, this is a story where almost every major character is a woman. You've exclusively hired men to write the screenplay.

And probably men, you know, who like me find, There's a great quote in September issue, Anna Wintour says, there's something about fashion that can make people very nervous. I'm guessing all of these men were made very nervous by fashion, you know, as I am. And, yeah, it doesn't seem like the right fit. That's spot on because apparently they had turned this into basically like a Zoolander-esque skewering of the fashion world, which to your point, I think that's what you do if you don't, A, care about it and be like understand. Right.

Right. So in fairness to these folks, there were a few big problems. with adapting the book first. It's basically just a series of anecdotes. Like, there really is not a strong narrative through line pushing you towards a climax at all in this. I've been rereading it. I'm not totally done with it, but like, it's a bit strange. It's, the structure is weird. It almost kind of loops back on itself over and over again. It's just sort of these, like, series of vignettes of her life with her boss. And then it'll, like, start in one place and then kind of jump back to explain, like, how she got to this kind of, you know, the worst part of her day.

just over and over and over again. And it really doesn't have like any kind of driving narrative to it. So that is a pretty big challenge for this movie. There also is not a strong third act at all. According to Elizabeth Gabler, then president of Fox 2000, quote, getting that third act narrative was one of the biggest challenges of my job ever. We had all these plot points that were carryovers from the book. So there were external reasons for Andy to make a decision whether she wanted to keep her job because Miranda's threat was, if you leave, you don't have your job anymore. Servicing those subplots was crippling, and it was liberating to finally say,

let's not make it about that. Let's make it about her decision, which I think is a very smart change they make for the movie. So obviously, they had a lot to fix in order to make it a successful movie and nobody had really nailed it yet. And meanwhile, the studio was hunting for a director. And they really wanted someone with a ton

of very broad, like, sitcom-style comedy experience, which I think gives you a clue as to what those early iterations of the screenplay might have been like. This did make David Frankel a pretty weird fit. He'd only directed one feature at that point and was much better known for his work directing episodes of Band of Brothers, Sex in the City, and Entourage. Although to me, someone who's directed Sex in the City and Entourage. Sex in the City is a perfect fit. Exactly. It is a perfect fit. Also explains how Adrian Grenier got into this film. Yes, it does indeed. You know, I don't think his career's ever really recovered

because of how much we all started to hate him on like the second or third. I know. And he's just an actor. I think it's unfair. Like, we forever saw him as this motherfucker from that film. And I don't think he ever got it back. No, between this and entourage, which he's actually, he does a good job in both. It's fantastic.

I don't think anyone made it out of entourage alive if you look at that cast. Yeah, yeah, true. Yeah, you're right. I guess they didn't. But it turns out Wendy Feinerman had had her eye on David Frankel for a pretty long time. And even though he didn't really have a ton of experience with what, broad comedy or fashion, he was intrigued and he agreed to a call with Finerman. And he's like, well, I should probably read the book and I guess read the script before this call. So he did that

and then promptly went into a panic spiral saying, quote, four very talented writers had been working for a couple of years adapting it. Having read the book, there were moments of more honesty and emotion in some of the scenes which their movie turned into campy satire. So I bailed on the call with Wendy and abandoned the meeting. And then he said this. Miranda was a witch and Andy's motivation was to get her revenge. There was a lot of conflict that ended with Miranda being humiliated. I felt that wasn't satisfying. My view was that we should be grateful for excellence. Why do the excellent people have to be nice? I love that. I think that is such a smart take. That's very interesting. Yeah. So 10 days later, his agent called him up and was like, hey, did you

like the script? And he's like, no, I absolutely did not. And his agent kindly explained to him, okay, this is what directors do, find a germ, a nugget of something that appeals to you the first time through and then your job is to shape it into the movie that you love. And he's like, oh, okay. So he goes ahead, meets with Wendy, and then uses the entire meeting to tell her everything he didn't like about the script and how he would fix it. He said he wanted to celebrate Miranda, just as much as expose her, and turn this into a real coming of age story for Andy. It's about learning to be great at something. This worked, and with some help from Wendy, Frankl sold Fox on his vision for the film, and he was hired. But this was basically an entirely different movie than what

they had on paper. So they decided to find another screenwriter to start completely from scratch. And this time, they had a novel thought. Any guesses what was different about this screenwriter? A woman, perhaps? A woman! It's a lady. We did it, Joe. So in Thanksgiving of 2004, the relatively unknown Aline Brosh McKenna was hired, and she immediately clicked with Frankel's vision for the film. And it was very personal for her. According to McKenna who'd grown up in New Jersey, quote, Nigel's speech about how it's a beacon of hope that he read under the covers with flashlight, I wrote that as an homage to all of us for whom those fashion magazines were a peek into this world. There was no internet, so it was really hard to access that sense of what it meant to trot around the globe.

Fashion magazines were very important for widening your horizons. I agree. As a little kid in Richmond, Virginia, I love reading fashion magazines. It really was so different before the internet was around. But producers were very eager to get the show on the road, and so she turned in her first draft in one month. Chris, you're a screenwriter. What's the fastest you've ever turned in a draft? I technically had to do one a little faster than that, and I would never recommend it.

Okay, wow. Humble brag. No, she did more changes, obviously. I did a, it was like a light polish on something in a couple weeks. Okay. Considering what she did, that's crazy. She rewrote the whole thing. Yeah, like normally eight to ten weeks would be much more normal. That would still be quick.

Wow, okay. Something interesting that McKenna did was she made a point not to research Anna Wintour and instead chose to treat the Miranda Priestley in the book, as just that, Miranda Priestley. This is so smart, also because the book is so detailed. Like, it is basically just a transcription of everything that happened in that office down to the letter. A couple of interesting things that did get lost in the book-to-screen adaptation that I do

want to call out, though. Andy Sachs is very explicitly Jewish in the book. As is Miranda Priestley, there is a whole big reveal about Miranda's background that she grew up in a very poor Orthodox Jewish family in London. I do think it's interesting that they, erase basically any ethnicity from the movie in several roles. This is one of those cases. Nigel is the other.

Is Anna Wintour Jewish? No. Yeah, because wasn't her dad, the editor of the London Evening Standard? Yes. Yeah. Interesting. I think that's probably why in order to... Yeah.

Oh, that's a good point, to tie it more closely to her. Yeah. Although she's not British. Merrill Streep is not British in the movie, which I do think is interesting. Yeah, but she's got that same accent. In Atlantic. Yeah. Yes, I agree.

Yeah, that's true. Because Wintour doesn't sound always fully British to me either. No. Like when I listen to her. Yeah. They sound like Wasby New Yorkers. Mm-hmm. Yes, true.

A couple other little tiny details. She's from Connecticut in the book. She went to Brown, not Northwestern. Her boyfriend is Alex, not Nate. He's very different. He is a school teacher for underprivileged children, although I will say the book handles that in a very ham-fisted early aughts way in terms of who the underprivileged children are.

And he is sort of unendingly supportive of her. She is a lot less likable. Like the quibbles that he has with her in the book are extremely reasonable. and she really does treat him like shit. So it is interesting to me that they flip that. She also has a much stronger personality in the book, which I kind of didn't mind. Now, while the movie may have softened Andy's edges,

it did harden those of the people around her. McKenna said she pulled insult inspiration from Don Rickles to come up with some of Miranda and Emily's lines. And she actually did speak to one insider at Vogue who read the script and said everyone was way too nice. So she did a pass punching up all of the insults. And also changed Nigel, who is a composite kind of of two characters in the book, but ends up being essentially a whitewashing of the real André Leon Talley. That's who I was wondering in the September issue. That's kind of who I thought it might be.

It's absolutely him. They turn him from a sort of warm, friendly mentor into a, quote, mean mentor, the mentor who tells Andy what she's really doing wrong. It's an important thing in your 20s to recognize when you're failing. I know, but Stanley Toucci's delivery of it is just still so warm. He just can't be mean in anything. I know. who I feel like if they were going to do more of an Andre Leon Talley, I just thought of Titus Burgess immediately. Oh, yeah. Oh, my God, yes. He would be so good in that role. Yeah. Yeah, so good. He would be great. If they ever did a more true-to-life version, maybe. They do a Broadway version of Devil Wars Prada. They better hire him. And let him sing. Absolutely. So you may have noticed that I said she spoke to one

insider, and that's because it proved very difficult to get anyone from the fashion industry to talk to her about this movie. Yeah. Because Anna Wintor, scared the shit out of everyone. There were rumors that she had waged a campaign against Robert Altman's film Predaporte back in the 90s and that she'd been speed-dialing designers to tell them not to participate in The Devil Wars Prada. Of course, Vogue denied this. They were like, no, obviously not. No, no calls were made. There'll be no retribution if anyone wants to participate. Now, all right, I want to go back to the insults, and I want to talk about one particular insult that McKenna added to the film, which is, take a chance, hire the smart, fat girl. Fat girl. Yeah. I will never not laugh at this line.

Obviously, it is absurd because Anne Hathaway is gorgeous and not even remotely fat. But I do feel as though that is a nod to how insane it is. I don't think they mean it. I feel the way that they cut immediately to Anne Hathaway's face being like, what in the fuck are you saying? I think that was a really important moment of stepping outside of the industry being like this shit is bullshit. That's just what I took from it.

That's exactly right. And the screenwriter said this herself. She said, one of the things that's very palpable about, fashion is that it's very hard to be overweight. It's a world where being thin is prized, partly because of the sample sizes floating around. I thought that her describing Andy as a fat person says a lot about the values of that world. Where any place else, Andy would be considered incredibly skinny. It's also pretty different from I was thinking of love actually. Oh my God. The woman who works in the prime minister's office and where everyone just relentlessly describes her.

Talks about her huge thighs. Her huge thighs and huge butt. And she's gorgeous. Yeah, that one is crazy. Candidly, like her physique would be quite prized, right? And now, culturally, like... Well, maybe two years ago, but yeah. Yeah, sure. Okay, I'm a little behind the time. So, cut me some slack. 24, let's fucking go, Martin McConction.

But 2026, we're right back to the Devil Wears Prada. It's actually perfect timing for the second one to be coming out, as we have circled right back around culturally to the Azenpic era supersized. Oh, yeah, that's true. Zero vibes. Yeah. We're going to talk a little bit more about that as it pertains to the Devil Wars Prada, too, at the end of this. The reason I'm calling out this moment is because I agree with you, Jamila.

This one works for me. This one felt like it was for us. That was the one jibe that felt that it was for us to show how insane this is. I agree. But here's my main problem with the way that the movie handles this. Is that Anne Hathaway, by her own admission, did have to lose quite a bit of weight for the role. So much so that they had to add a prosthetic butt pad to her during this whole size six setup that, of course, they would later remove. when she's championed for getting down to a size four.

Well, I was going to say she arcs toward a four, which is... That's what bothers me. It undercuts everything. It does. I don't know why they did that, because it's not celebrated in the same way in the book at all. I think that was a mistake. I get what they're trying to do,

and I believe that they thought that they were saying something different than the way that I think it actually comes across. No, I think it was a combination of both. I think that one moment that we were celebrating showed situational awareness, and I do agree that to an extent they're just telling it how it really was in the fashion industry. But I also think that it was hyper-normalized

to see weight loss as part of a transformation in a woman that we would glorify. You know, it wasn't weird back then. You know, that line, I'm just one stomach flew away from my goal weight that Emily Blunt says, I think when they're going up the stairs. I literally haven't seen this film in a year, but this is how many times I've seen this fucking movie.

But as she's saying that, like that sentence alone entered the lexicon where until COVID, for the 20 years that film had been out almost, or like 16 years that film had been out. Anytime I got sick, my girlfriends wanted to come over to try and get what I had because they'd be jealous that I was going to lose weight and they wanted to lose weight because it felt like fat camp, you know, free fat camp is to get really sick. Yeah. Tell them just put their kid in daycare.

You'll be vomiting. Exactly. But that's what 20-year-olds were like after that moment. Like that moment normalized like thin, at all costs. And it cemented into our generation that thinness equals success,

thinness equals acceptance. Thinness means you get to dress better. It was like she could have dressed amazingly in all of those same outfits at the size fucking six or eight or ten or whatever. And she would have looked amazing. Yeah. But it was a subliminal message dropped in.

And that was the values of the time. That was the values of Hollywood for sure. I agree. They would have unbelievably thin women and she would eat a tub of ice cream in the movie. And the men would be joking about what a fat pig she was, you know. It was an insane time. So I don't want to say that we just misinterpreted it. No, no, no. I think you're right. I think that this movie, this is my one,

honestly, one quibble with this movie is it does quite a bit of have your cake and eat it too, or don't eat it, I suppose, with this. And, you know, Anne Hathaway said in an interview around the time this came out that she and Emily Blunt would like clutch at each other and cry because they were so hungry because they had lost so much weight during this. By the way, that article has been scrubbed, but I found it. Well done. Wayback Machine. Let's go. Way Back Machine.

Yes, I pulled a lot from the Way Back Machine for this because much of it had been scrubbed. So also, Anne Hathaway famously took her butt pad home and had it framed with Andy's ass written underneath it, which is kind of funny, but also makes me a little sad. Devastair. So since we're talking about our stars, let's go ahead and dive into casting. And it seems that they did start with Miranda, so we will too. Merrill Streep is like kind of the reason this movie got made. The film was not even officially greenlit until Tom Rothman secured Meryl Streep for the role in 2005.

And the early 2000s were a pretty fun and interesting time for Meryl. She had kind of started to take some steps away from her more serious roles. It had brought her an Oscar nomination for her part in Spike Jones's adaptation, which I love so much. She does deliver one of my favorite lines in the entire movie. Chris, do you remember? Which one? That's what she screams at the end. You've ruined my life, you fat fuck!

Yeah. Incredible. I just want to be a baby again. I want to be a baby. She's so good. She'd also appeared in Lemony Snicket's series of unfortunate events. And she was kind of just looking for more fun roles. And it really was not about making money.

She was just like, she's like, I've done the serious stuff. I'm out to have some fun now. I also feel like she was an unbelievably beautiful woman who was always disowned by the fashion industry. She was always someone who no one took any interest in what she wore, no one took any interest in how beautiful. Which is crazy. theme throughout her youthful interviews of how unattractive she was, you know, made to feel by people because she had that beautiful long nose. And she was told, you know, you need to look more like an all-American girl to be successful. You'll never be. She was so discouraged at the start of her career.

And then throughout her career, she was a bit like Emma Thompson, another gorgeous woman who was just treated as if you're like, oh, you're not really in with the in crowd. She was one of the least celebrated superstar women. And so I imagine this is also quite a fun little fuck you to an industry that largely shunned her even though she added so much value and worth to any of the bullshit they were doing. I agree.

And also I think about her in like Kramer versus Kramer and she is just stunning. The most beautiful. Stunning. We need to cover that. That was a tough. She did not have a good time working with Dustin Hoffman on that movie. No, that slap, Jesus Christ.

Yeah. Dustin Hoffman, we'll get there. Now, according to Entertainment Weekly, Michelle Pfeiffer, Glenn Close, and Catherine Zeta Jones were all considered for the role. I could see Glenn Close and Michelle Pfeiffer. I don't really see Catherine Zeta Jones the same way. Too young. That's ridiculous. Yeah, that's true. That's true. She had just done like intolerable cruelty. She would have been way too young.

Oh, yeah, yeah, yeah. I don't think she looks right at all for that. But Carla Hacken and Wendy Feinerman were both on the Merrill or Bust train from the beginning. However, not everyone shared their confidence. Finerman revealed that Streep was almost passed over because of doubts as to whether or not she could be funny. That's crazy to me. She just did adaptation, which truly she made me laugh out loud

so many times in that. It is a different type of humor, but I wouldn't necessarily look at Close and Fyfer any differently, is my point. Exactly. Fyfer, maybe, because of, like, Batman. Yeah.

Okay, that's fair. Maybe it still wasn't like comedy comedy. This is sitcom comedy, you know, that they were looking for. And I think it's maybe not just that they don't know if she can do it. It's also that they imagine that if people see that it's a Merrill Street movie,

they'll imagine it's a very serious Oscar-worthy, gravitas-laden film. That's true. But of course, it does end up getting her an Oscar nomination. But she got along great with David Frankel, who said, quote, when I met Merrill, we talked about, what would you sacrifice to be excellent? She also wanted to make a movie that at least mocked the tyranny of the Thin. Now, I want to say, I very much get the impression that Merrill was more on the side of mocking

this than kind of anyone else making the movie. She was very angry. Behind the scene, she was always trying to encourage Anne Hathrow. way to eat to not lose weight. Yes. Yeah. She vocally was like, you don't need to be doing this. But of course, she did because they were telling her to more on that in a few minutes. Well, Lizzie, it does remind me of the Grace Coddington moment in the September issue when she was looking at the photo of the cameraman. And they said they were going to basically Photoshop out his belly. Yeah. And she's like, I don't want you to do that. I want you to look like a person. Like people should look like people. Not everybody needs

to look like models. It was a very interesting moment behind the scenes. She's fascinating. I really, I could have watched three more hours of Grace Coddington. If you all haven't watched the September issue, it is streaming on Prime right now, and I highly recommend it. It's a nice little companion piece, the Deppel Wars Prada, and they do something very smart, which by the end of it, it really is more about Grace Coddington and a little bit Andre Leontali, although not as much about him, but then it is about Anna Wintour.

And I think that's because they realize that they're both more interesting than Anna Wintour. Wintour is pretty flat. She's pretty inaccessible. Yeah, she does not let you in. Merrill did have a few conditions that had to be met before she would officially sign on. She insisted on a business of fashion scene. This became the Cerulian sweater scene. She wanted it to be taken seriously and explain how it impacts daily life. By the way, a little fun fact on that cerulean sweater monologue.

It's completely made up. Most of the detail was just invented by McKenna because it sounded real. And then the second thing that she required was the scene where Miranda appears completely makeup and fashion-free in the hotel room where she tells Andy about her divorce. She said, we have to see Miranda without her, quote, protective glaze. These are such smart additions, like kind of essential additions, I think, to this movie.

Two of my favorite parts of the film. Yeah, two of the most iconic parts of the movie. She's such a producer, isn't she? Mm-hmm. She's so smart. She also required a lot more money than they initially offered, to which I say, good for you, Merrill. She said, quote,

the offer was to my mind, if not insulting, not perhaps reflective of my actual value to the project. 100%. There was my goodbye moment, and then they doubled the offer. I was 55, and I had just learned at a very late date how to deal on my own behalf. She made somewhere between $4 and $5 million for the role. Good for you. She is the movie. She makes the movie. She does. Yeah, 100% she is the movie. This may be hard to fathom, but Adrian Grenier was one of the biggest stars in the cast at this time. He was peak entourage fame, and so when he was cast as Nate, that was another big boon to the movie. Simon Baker, on the other hand, he's a few years away from the mentalist at this point, and so he actually was not a big name at all. He'd had some small but recognizable roles across American and Australian film and TV. By no means, was he a star?

I love Simon Baker, and I'm totally with you. Every time I watch this, I'm like, my God, leave him. Go with Christian. Good Lord. I hate Christian. I'm so surprised. You do, you do, really. Yeah.

Why? I hate the way he's written. I just find him very charming. I want to get her like a good vibrator and get her away from both of these men. I found him dripping with sleaze. Oh, he is. Yes, he is. But, like, I guess, am I totally off base?

Maybe that's your thing. I feel, like, for me, that's, like, I think I hate smooth people. So I think that's probably, I just don't trust anyone who isn't, like, fallible and awkward. That's fair. So I think that's probably just my personal taste where I was, like, neither of these men suit this woman at all. And he just, like, seemed like he has a date rape drug, you know, in his pocket. But that's just my personal feeling. Sorry.

Sorry. I could see it. I guess maybe it's my love of Simon Baker in general that is bleeding through because I find him very charming. But I will say upon this rewatch, I didn't find anything that Christian did particularly bad. I don't know. He's fine. What does he do that so bad? He's, I mean...

I feel like he's dangling the professional connections, like, you know, to try to get the sex from her. Yeah, he's definitely got a casting couch. Yes, totally. He knows she's got a boyfriend. He knows she's like inappropriately young for him. He's an incredibly sleazy character. Okay, I'm wrong. I'll crawl back into my hole.

No, no, no. Here's where I agree. He's an incredibly sleazy character. I still find Simon Baker very charming. He is. And I think he does a great American accent. Oh, yeah. Also go see Land of the Dead.

He's very good as the lead of that movie. Totally. No disrespect to the actor, but it's just like he's inappropriately older than her. Super inappropriate. She's clearly an awe of him. It's a total abuse of power and experience. My 16-year-old brain was like, that's the good one. I know, but what were our options back then?

Do you know what I mean? That's what I'm saying. I just find Adrian Grenmay is so unattractive, poor man. You know, it was that or Paul Blart Mall Cop. You know, we were told it's one of these two, or Paul Blart Mallcup. Like, we weren't given any, like, middle ground of someone. It's either Seth Rogen and knocked up or this is the villain. Exactly.

And all the men who were kind and good and emotionally intelligent were put in a sweater vest and marketed as the weak beta, soy cuck, that the woman always passes over for the bad boy in the leather jacket. We didn't have those words yet, though. No. That is true. Soyboy is my favorite manosphere term. It makes me laugh every time I hear it.

It's so ridiculous. But back then, you know, those were the, you know, we were given stereotype options of men who are mentally and emotionally unavailable and manipulative. And we were told to go after him and save him and fix him. And we were never told to go with someone nice who cared about us and our dreams. No, no. And I feel as though this just was a continuation of that.

Absolutely. Fucking horseshit. But anyway, I'll do well. So the part of Emily was particularly difficult to cast, and Frankel saw over 100 actresses for the part. None of them were right. Now, Emily Blunt had mostly acted in TV movies at this point, but she was on the Fox lot at the time because she was deep in callbacks for Aragon. Oh. But, yeah, it turns out in one of the meetings she took on the lot, a casting associate asked her to read for the Devil Wars Prada.

And she was running late. She's trying to make a flight. She had on sweatpants, so she's just like, whatever. And she read the sides very flustered, very fast in a British accent. sent. Frankl saw this tape and he was like, that's my Emily. I love her. I want her exactly like this. But he actually had to wait for Aragon to pass on her because that's the part she wanted and that was the higher profile film. They finally did pass on her and he called her house in England, got her mother who informed him that she was out getting very plastered with her sister, sad to have lost the

Aragon role and told him to call her cell phone. And he did and he reached her in the bathroom of a dive bar in London where he said, listen, I would love to cast you off the tape, but the studio wants to see you one more time. So can you do what you did, but dress the part more? And so she did one more screen test, and she got the part. And it is worth mentioning, the character Emily in the book is potentially the most different from book to screen, and that has everything to do with Emily Blunt, because she and McKenna literally went in and rewrote that character. They added all of those funny lines, the Britishisms. And Blunt said she took some info from people in the real world, saying, quote, I saw a mother speaking to her child in a supermarket when we were shooting that film.

It's a line that gets quoted back to me now. She yelled at her kid and she kind of opened and closed her hand and she goes, yeah, I'm hearing this and I want to hear this. I went and put it in the movie. Poor kid. She stole the film. A hundred percent. She steals this movie.

Stole the movie. I think she's why I rewatch it. She's so funny. Obviously Anne Hathaway's a delight. But I watched the movie for Emily Blunt for just those little, just bite-sized moments of her utter unapologetic villain vibes. And just the way she eats that chocolate pot in the hospital because she hasn't eaten in so long

that this disgusting hospital prison food like tastes so amazing to her. And she's like licking the lid or whatever. I just thought she humanised such a nightmareish role so brilliantly. I remember just thinking, who the fuck is that? And she's why I watched it again that day in the cinema. That was it for me.

was just like, me and John Krasinski both were just like, that's it, I'm in love with her. That's my woman. I'm going to watch her and support her and everything she does forever. But she made that fucking movie. I agree with you. She makes me laugh out loud more than anybody else in this movie. Yeah. All right. Now, before we get to our final piece of the puzzle, I want to talk about the casting of Nigel because there's a little bit of scandal around it. So before Stanley Tucci was attached, the production did a round of auditions, but not with

actors. They auditioned several real-life fashion industry people. including Simon Dunin, the former creative director of Barney's New York. And here's how Dunin said his audition went. Quote, after I delivered my lines, Mr. Frankel asked me about various people at Vogue, including Miss Winter. When I told him that the editor-in-chief was straightforward, highly professional, an incredible mother and extremely well-liked by her staff, in sharp contrast to Miss Weisberger's implied portrait, he glazed over.

Soon, Dunin realized that celebrity stylists Robert Verdi and Philip Block had also been asked to audition. But mere days after Dunin had read for Frankl, Stanley Tucci was announced as playing Nigel. So here's what Duhin said publicly about this. Quote, this whole charade I theorized was nothing more than a carefully orchestrated piece of unpaid research. Yeah, try to get them on camera talking about Anna Wintour. Yeah, he said, We gaze had been dragged in to swish it up on film, no less, for the deletation of some precast overpaid straight actor. This Cespian would then fashion his characterization from our mincings.

You know what that's happened to me before? Really? When I was doing an audition for a movie that I think was with Jennifer Garner, a few years ago, the casting director, asked me all these private questions about Kristen Bell and clearly, like, had it in for Kristen Bell and was like, do you think she would have been more successful? Had she been prettier?

And I was like, I think she's very good looking, and she's also really fucking successful. She's a household name around the world. I think she's fine. I think she's doing fine. She's doing great, and she looks great. And she asked me all these private questions about, like Kristen's marriage to Dax.

What? And I was like, oh, shit, you have a problem personally with Kristen Bell. And because I'm in a show where I spend all day with her, you've only brought me in to try and get shit from me about Kristen, which I would never do. And it was in between two scenes. And so in the next scene, I have to die, which is already humiliating to pretend to be shot in like Mime up against a wall.

And I'd never done a death scene before because it was like my second ever audition. And the good place was my first ever audition. This was like my second ever audition. And I was having to do drama, which I didn't know how to do. And she was so angry with me because I wouldn't give her a single nugget about Kristen Bell that then she like was just like read the sides like, yeah. And then bang, you've been shot. Yeah.

Okay. Thank you. And didn't even look at me. And just I left the room and I never heard anything back. And I was like, you motherfucker. These fuckers, this industry. That's bizarre. What are you doing with that information?

It's just like your own personal... Does she have a Kristen Bell voodoo doll? I had no idea, but she was obsessed, and I didn't give her anything. And I didn't get the job. But, like, fuck, working with someone like that. So tell me, what's Kristen really like? Well, if it makes you feel any better, my daughter may or may not be, at least partially named after Eleanor Sheldrob. Oh, perfect.

The good place. Great. Aw. Well, so Stanley Tucci came out, and he was like, no. He said, I don't know why someone would write this. such a piece. They really did not know what they wanted to do with this part. I think he's imagining a much more Machiavellian scenario than actually exists. All I know is someone called me, and I realized this was a great part. Initially, I thought, oh, okay, I believe Stanley Tucci,

but the more I started thinking about it, I kind of believe Simon Dune. Who's to say, it's totally, look, both options are totally possible, but I think Simon's one is more plausible given the nature of Hollywood. I agree. Well, is there a version where Tucci's unaware of it? Yes. Frankl has used the information, right? You see what I'm saying, to inform the way he's going to direct him. Well, Tucci is also the salt of the earth. Like, I couldn't watch a movie where he played a paedophile or a rapist or something because I was like, the lovely bones.

He's going to make me fucking like, he's going to make me, yeah, he's going to make me sympathize. It's rough. Because he's just so lovely that it's so impossible to hate him that I was like, I can't watch anything where he's actually a villain. Otherwise, I'll sympathize with a villain. So I have to avoid whenever he takes a dark turn because it'll do something weird to me. I'm just, I ride at dawn for Stanley Tucci. Of course.

We all do. My secret pitch for that movie is they should have flipped the casting between Stanley Tucci and Mark Wahlberg. Oh, God. I don't want to see Mark Wahlberg play a murdering pedophile either. That's scary for different reasons. But yes. So it is interesting, though, because Tucci was apparently cast a couple of weeks into shooting, and he actually accepted the role a few days before they started filming him. So it does seem like maybe they had a hard time filling this role. Perhaps they were casting a wide net. They went to, you know, real people in the fashion industry. Who knows? He's also straight playing gay. Yes, yes. I think that was Simon's point about him being able to watch them on camera, which is a valid point. All right, step aside half a haters. It's time to talk about Andy Sacks.

So Anne Hathaway was not the first choice to play Andy, nor was she the second, third, fourth, fifth, sixth, seventh, or eighth. She was the ninth choice for this role. Any guesses who the studio's top choice was? Huge star at the time coming in hot off of Mean Girls, The Notebook. Oh. Oh, no way. Rachel McAdams? Rachel McAdams. Who would be in an Aileen Brosh-McKennas script morning glory a few years later.

Yeah. They were desperate for her. So she was actually filming the Family Stone on the Fox lot at the time, and they offered her... Love the Family Stone. It's great. It's great. It's an incredible Christmas movie. They offered her this role three times, and she kept saying no.

She did not want to do more commercial work at this point. And Frankel said, you know, at the time, it would be easy to perceive the movie as kind of a simplistic Cinderella tale, and she wanted to do more sophisticated work than that. Also, like, we don't know where the script was at this point. It's quite possible she was reading earlier iterations. By the way, it's not a great showcase of acting talent that film. That's not to discredit Anne Hathaway, who I think is a phenomenon of our generation. Well, that's the least interesting part in the whole movie. There's no real acting chops other than, like, a bit of frustration or a bit of tension about, you know, like a bit of stress. Really, it's a fluff role where you are playing the exposition

lead and everyone else gets to be colorful and the storyline happens everywhere apart from really you. Yeah. You're the audience's point of entry into a very weird world. Which is hard. That's also a hard job. It's totally a hard job. It does it incredibly well, but it's not a fun job. Yeah, it's not a job that, like, I think any actor would be like, oh, this is going to make a real impact. However, the commercial success of that movie made Anne Hathaway a Bonafide, A-List superstar, faster than Rachel McAdams. Well, no, I guess the notebook was the biggest film in the world. So I guess, I guess, guess maybe she also didn't need it as much as Anne Hathaway needed it. She graduated Anna Hathaway into like, I'm an adult making real blockbuster movies.

Totally. So other actresses considered before Anne were Kirsten Dunst, Scarlett Johansson, Natalie Portman, and Kate Hudson. And Kate Hudson has openly said that she regrets not taking the role. She apparently really only turned it down because of a scheduling conflict. Kate would have been phenomenal. She would have been great. Any of those would have been great.

Yeah. I mean, a lot of them are just like, no, they're great, but they're just like, they're very. They're very serious and very grounded. Like, this role required a levity that Anne Hathaway is a master at whilst also being able to be, like, Le Miserables, like, deep, traumatized, wrecked. And McAdams can do that too.

Like, Rachel McAdams could be so funny. Yeah, mean girls was so hilarious. Yeah. There's one in that list, I think, could absolutely do this, and it's Kirsten Dunst because of Drop Dead Gorgeous alone. For sure. And Dick, she's so funny. She's so funny. I think she could have done this.

Yeah. But I agree with you on the other ones, for sure. So finally, the casting director moved all the way down to the bottom of her list to Anne Hathaway. At this point, best known for playing princesses and teen-centric movies like Ella Enchanted and The Princess Diaries. And Fox was like, no thank you. They wanted a dramatic actress. They didn't see her as that.

They saw her as a teen. Hadn't she done Brokeback Mountain? It had not come out yet. Oh. That's going to pop up in just a second. But Anne Hathaway was determined. According to Elizabeth Gabler, she said, quote, I remember Anne sitting on my sofa in my office and explaining why she wanted to do this, why she had to play the role, and giving script notes about the third act.

When I look back on it, it wasn't exactly what we ended up doing, but her sensibilities were completely aligned with what we did end up doing. Annie never gave up. She never stopped campaigning, calling. She came into Carla Hacken's office and wrote in her Zen Garden, hire me. You have to admire it. Yeah, that's nuts. That's so intense, but also she was such a key. Like, now I could never imagine anyone else playing that role. No. She is correct that it was made for her. Yeah. And even as much as I like, I'm. I'm a Kate Hudson stand for life. I love her. But Anne Hathaway brought something of vulnerability

that was so fucking magical to that movie. I think also there is something about Anne Hathaway's looks, even though she's absolutely stunning and obviously does not look like a real person in any way, shape, or form. But there is something that I think reads to Hollywood as more accessible about Anne Hathaway than someone like Kate Hudson, I think. That's also it is that like the transformation of like the hairdo and the new makeup and stuff and the nicer clothes was dramatic on her. Yes. Obviously when you zoom in on that face and the blue cerulean blue sweater, she's still gorgeous. But you're right. It was a more like, holy shit moment.

Yeah. So the filmmaking team is like, all right, great. We found our Andy. And they actually started negotiating her deal when the studio said, not so fast. They were not on board. And it was Meryl Streep who got her over the line. because Merrill saw her performance in Brokeback Mountain, which she is great in. And Streep personally called then chairman and CEO of Fox Tom Rothman and said, she's great, you're dumb, go ahead and hire her. And I'm paraphrasing, but that was that got her cast. Now, meanwhile, production designer Jess Gonshore was having a hell of a time. He had only one feature credit to his name at this point, which was Capote, and that had not come out yet, when the Devil Worse Prada was kicking off production.

and he had to figure out how to recreate Anna Wintour's office. Now, according to an article around the time of the film's release, he had absolutely no way of seeing it in person, so he just had to go off of one photo he'd found online, except many years later, David Frankel told a very different story. He said the only real contact they had with Vogue for this movie was when Gonshore snuck into the offices and managed to stick his head in Anna Wintor's office long enough to get every detail of it.

And folks, I would like to show you a side by side. Lizzie, it reminds me of how they designed the bomber in Dr. Strangelove, the way you described that, where they, like, got the one photo from the magazine, and they recreated it perfectly. Oh, holy shit, lull. Yeah. Down to the hexagon mirror. I know. I know.

It's amazing. Isn't that incredible? Wow. Yeah. Well, it's funny how the movie did it better. The movies is, like, slightly more aesthetically pleasing. You know what I mean? Yeah.

And according to Frankel, Anna redecorated as soon as the film came out. I assume because she saw her exact office on the movie. Well, I also assume her second assistant did. Oh, yeah, yeah, yeah. She didn't do it, surely. Now, Gondchor was also struggling to find any locations for the film, which they planned to shoot in New York City. It's a movie set in New York City. Doesn't seem like this should be too hard. Any ideas why this might have been a problem? Because they had no budget. Well, not no budget, but they had a low budget. Well, that's not exactly it, but let's talk about that for a second. Yeah, I was reading

Meryl Streep talking about the first movie saying, like, we had huge budget constraints. And she said that that was typical. That's true. They had about $35 million, which was quite low for this. Which, considering how flashy and beautiful this film was and had to be to sell it as genuinely evocative of the fashion industry, she said that they had huge budget constraints. I did any movie that was designed for a female audience, which is so ridiculous, given that women are still 80% of the consumer market. And we are the ones who go out and support.

And buy shit. Yeah, maybe not female superhero movies, but other shit, like women go out and they buy. and they support. And really, it's only after films like Barbie, you know, breaking a billion that they've realized the studios that, okay, women and girls are actually, were always the target movie audience. And so she said that they had a much healthier budget for the sequel of the Devil Wears Prada. Well, good. They earned it. But yeah, you're 100% right. They had about $35 million for this. And again, we know four or five million of that went to Merrill Streep right away. So that is not a big budget at all. We're going to get into some of the

issues the budget did cause, but the location's a little bit of a different problem. It turns out no one wanted to let them use their spaces because they were all so scared of Anna Wintour. Interesting. So if you think about what they're filming and where they're filming, the Metropolitan Museum, absolutely no, because of the Metball. They said no way. Bryant Park, nope, they do Fashion Week, not doing that. The Museum of Modern Art is like, uh, fuck right off. We're not doing that. She didn't care. She was breezy. She didn't care. She didn't care, Jamila. Yeah. She's bored. She's bored by it all. She's not. You know she's calling these people in her crypt at night. She's not her second assistant. Like, I think it's a mob-style situation.

I know, but she's Tony and she's calling the fucking shot. That's my point. Exactly. She knows how to do it. There is a moment in the book where it's revealed that Andy has to call this chef and, like, scream at him as Miranda's directing her exactly what to say. and I 100% believe that that is probably what's happening here. For sure. Iconic Upper East Side Apartments, where they had hoped to shoot Miranda's home, had co-op boards that refused the film crew's entry into the buildings. Weeks went by without them being able to secure a single location

and actually got so bad that Frankel and the rest of the team wondered if this might be the thing that kills the movie. They could not get filming locations around New York. Finally, a friend of Wendy Finerman let them use their Upper East Side townhouse. This is why the layout in the movie, of that townhouse is so different from what's in the book. It's because it was the only thing that they could get. So they had to literally change that whole sequence about don't go upstairs, although I think it works better in the movie because of that. Yeah. And last but not least,

they finally found a location for the ball event, and it was the one place that according to Frankl Anna Wintour had no influence. It was the Museum of Natural History. That's the only one that said, go ahead with the dinosaurs. So when the cast met up for the first time, Merrill Street pulled Anne Hathaway aside and said, I want you to know, I think you're going to be great, and I'm so happy to work with you. And that's the last nice thing I'm going to say to you. And this was true. She went method with Miranda Priestley, keeping herself apart from the rest of the cast for pretty much all of the shoot. For the first table read, she arrived 10 minutes late on purpose, so everyone would have to wait for her entrance. But it was worth the wait. Anne Hathaway said, quote, I think we all had an idea of what

Miranda would sound like. It was a strident, bossy, barking voice. So when Merrill opened her mouth and basically whispered. Everybody in the room drew a collective gasp. It was so unexpected and brilliant. Although I will say, have you heard Anna Wintour talk? Because it is also an imperceptible whisper. Yeah, that's true power, is making people come to you. Well, Meryl Streep did say she didn't based Priestley on Wintor. She actually said she pulled a lot from Clint Eastwood. She said, quote, he never ever raises his voice. Everyone has to lean in to listen and he is automatically the most powerful person in the room. But he is not finding. that I stole from Mike Nichols. The way the cruelest cutting remark, if it is delivered with a tiny

self-amused curlicue of irony, is the most effective instruction, the most memorable correction, because everyone laughs, even the target. The walk, I'm afraid, is mine. Now, as McKenna was flying home from the table reed, she realized she was sitting very close to the supermodel, Giselle Bunchen, and their plane was delayed two hours. So at Frankel's request, she walked over to her, asked if she'd like to be in the movie, and Bunchen said, sure, but she said, I don't want to play myself, and I want to play a bitch. And so McKenna wrote the cameo for her right then and there. Love that one. I love it too. And she's fun. She did have to ask Vogue's permission to appear in the film, which she got. All right. So production kicked off with a little bit of luck.

New York City's tax incentives for filming had just taken effect that essentially gave the film a 5% tax credit. And that's about where their luck ended. When Anne Hathaway was first hired, the production team told her to gain 10 pounds because of, you know, where Andy starts in the movie. And Anne Hathaway's like, great. She ate pizza, ice cream and beer for a month. But then she got to her first costume fitting with legendary costume designer Patricia Field, who was like, why did you gain 10 pounds? You need to fit into couture. This is not going to work. So Hathaway had to immediately take off the weight she had just gained and then some in order to be able to fit into the dresses in the film, which is a nightmare. And just in case you aren't familiar, Patricia Field is the

iconic costume designer behind sex in the city and much, much more this woman is a genius. But she was also having a terrible time on this film. You pointed this out, Jamila, but there's at least a million dollars worth of clothing used in the movie, but they, of course, did not have the budget to buy that much stuff. They had about $100,000 for the costume budget. Yeah, no one was going to lend them because they were scared of Anna. That's the problem. A hundred thousand dollars is a tiny, for a movie this size. For a movie about fashion, it's crazy. That's insane. It's crazy. That does not make sense. I know. Yeah. That's what they gave them. And I think maybe they did that because the assumption was, oh, designers will lend their clothes to us for this. Right.

But Anna Wintour strikes again, yes. Nobody wanted to lend their clothes to the film for fear of retaliation. It actually took one designer going against the grain and agreeing to lend their clothes for the floodgates to open. Any guesses who that designer may have been? Mark Jacobs? No. Oscar De Laurenti? Is it the Chanel?

It's Prada. Oh, lull, la, la, la, of course, because the film has done so much for their brand. Should have known. Yeah, yeah. Yeah, it's in the title. Yep. Muccia Prada did say she found the book awful, but ended up enjoying the film. And with Prada officially on board, the other designers came running.

So, Jamila, I have to ask, what is your favorite outfit of this movie? It's the first one of the... The montage? No, not the montage. It's the first one of the... Oh, the Chanel boots? The first time, it's the Chanel boots with the amazing jacket. And her hair is, like, insanely cut and layered.

and those are all kind of like 15 denier tights. It's so good. It's the chicest thing I've ever seen in my entire life. If I ever get to look like that just one time that put together with the big bag, I audibly gasped in the cinema when I saw her. And how triggered Emily Blunt gets and is like, shut up to Giselle is absolutely ideal. It's great. So that for me is like my favorite outfit of the movie.

It's beautiful. What about you? I love the long leather trench that she has. She has an outfit that is like multiple pieces of like brown leather when she's in the montage. And I do really love that one. But I also, I love the Chanel boots. Those are probably my two favorites. And I have mixed feelings about the cap sleeves on her gown in Paris, but that's fine. It looks beautiful on her. I'm just angry because I can't wear caps sleeves. Chris, I'm sorry, we can't leave you out of this. What is your favorite outfit in the Devil Wars Prada? It's her Harry Potter outfit. When she comes in, it's sort of Harry Potter. chic outfit. It's the first one after a transformation. It's the Chanel boots. She comes in. She's got that oversized blazer that, again, looks like it's inside out or something because of the way that they've

done the stitching. And she has a patch on it that looks like a Hogwarts patch, a Gryffindor patch. Great. So women see Chanel boots. You see Harry Potter. That tells us a lot. No. I see magic. You see magic. Fair enough. Thank you. All right. So it honestly is kind of amazing that they got Patricia Field in the first place, given how connected she is to the fashion industry. But she was basically just like, whatever, guys, no one knows who Anna Wintour is. Like inside the fashion industry, yes, people know who she is. But she said, you know, how many people know the name Anna Wintor? It's not a slur to Anna Wintor. It's that fashion is a small segment. I want to tell a bigger story, not a story of Anna Wintor. Yeah, she's also the fucking sex in the city.

You know what I mean? Like she's already made her money. She doesn't have to worry about her career. Right. So, Meryl Streep, not having a great time because she's method. She's not talking to anybody. That really sucked for her. Anne Hathaway, however, was having a lot. a terrible time because of a bit of life-imitating art. I don't know if you guys remember this. She was dating and living with a con man. Rafaelo Foliari, an Italian con man. I'm sorry, I have to take a second to talk about this. He was running a con, which she did not know about, obviously, where he was saying that his New York firm was helping the Catholic Church unload unwanted real estate properties at a discounted rate to help the church recover financially

from the sexual abuse scandals coming to light at the time, which she was. Such a crazy pitch. But he like leaned into this. He was like, I am personally connected to the Vatican. He had an altar in his office. He had a nun as his receptionist. Absolutely wild, wild, wild. But he was terrible to her. And apparently he would get angry at her when she had to work late. David Frankel said she was really emotional on set, particularly when the shoots ran long. He always made it a problem for her. She did eventually leave him in 2008, 10 days before he was dragged out of his parents' apartment. by the FBI, and he served four years in prison. And just so you know, Donald Trump had something to say about it. He said, quote, Anne Hathaway hasn't remained very loyal to him, has she? So when he had plenty of

money, she liked him, but then after that, not as good, right? I don't think that was the problem for Anne Hathaway, a multimillionaire movie star. Anyway, the whole thing was very humiliating for her. She eventually had to hand over tons of jewelry he'd bought her and her personal diaries. But it sounds like she was living with an emotionally abusive con man boyfriend while also trying to stay desperately thin, working her ass off on a movie she'd fought incredibly hard for, aka having honestly a much worse time than Andy Sacks does in the movie. And in December of 2005, filming wrapped. Now, the film was scheduled to release the same weekend as Brian Singer Superman Returns, which to your point, Jamila, had a budget of over $200 million. But before it came out, Anna Wintour

was invited to a private screening at the Paris Theater in New York. She came with her daughter, And even though she frequently would leave plays that she was very bored by, she stayed until the very end. And apparently her daughter leaned over and said, Mom, they really got you. So the Devil Wars Prada released wide on June 30th, 2006, and it absolutely tore up the box office. It made $326 million worldwide. And by the way, Superman Returns made $391 million worldwide, which yes is more money. But as we know on this podcast, that means that one probably about broke even, because of marketing and the cost of the movie, while the Devil Wars Prada was absolutely minting money.

Of course, the film was not at all bad for Anna Winter. She became a household name, ended 2006 as one of Barbara Walters' most fascinating people. And the film received two Oscar nominations, one for Patricia Fields' costume design, and one for Merrill Streep. Critics praised the film and Merrill's performance, but it also was a real sea change for the fashion industry. The Devil Wars Prada, too, will of course hit theaters on May 1st, and we will be reviewing it as a bonus episode, so stick around for that, but it's already made some headlines. I don't know if you've seen this, Jamila, but Streep and Hathaway attended Milan Fashion Week while filming, and they were reportedly both pretty horrified by how thin the models on the runways looked.

Streep revealed that Anne Hathaway headed straight for the producers and secured, quote, promises that the models in the show that we were putting together for our film would not be so skeletal. That's our go. Good for you, Anne Hathaway. Not good that that's a conversation that needs to be had, but I'm glad she did it. All right, let's end on a happy note. Anne Hathaway might not have found love on the set of the Devil Wars Prada, but Stanley Tucci did. So Stanley Tucci very sadly lost his beloved wife, Kate, a social worker who he'd been with since 1995 in 2009 following a battle with breast cancer. Yeah, but then Emily Blunt came to the rescue. So Tucci had met Emily Blunt's sister Felicity, a literary agent at the premiere of the

Devil Wars Prada, but a few years later they met again at Blunt's wedding to John Krasinski. They fell in love and married in 2012. Yes, there is a massive of 21-year age gap, something that made Stanley Tucci very nervous, but in the end, love won out, and they have been happily married ever since. All right, Jamila, this is how we end every episode. We like to ask, what went right? What went right with that film is it's an incredible time capsule of a very strange moment in history and in the industry. Yeah. I think it was cast perfectly. There's nobody I would have changed for any one of those roles. I think the casting director deserves an Oscar for that film. Merrill Streep set a new standard for female villains and also empathizing

with female villains. You know, we rarely empathize even with female heroes in film and she forced a through line that it was incredibly interesting about what it takes to make it to the top of an industry that is ultimately run by men, even if it presents as a female. That is a mask because the fashion industry is ultimately owned as of the studios, as of the music labels by men. And they use women kind of was like to go out and do their, you know, dogs body work whilst men sit in the shadows, making all the actual money from this. Dog's body.

Yeah. A British term I just learned. Indeed. So I think that the soundtrack was great. The fashion was phenomenal. It is a film that ultimately, I think, was trying to tell us that he was the real villain and telling us that he was a cunt.

And I think we all missed it because we were all drunk on patriarchy when we were young. And that her friends were dicks. and there was no charity offered to the boyfriend or to the friends. I don't know if that was subliminal or if I'm just being too charitable. No, I think you're right, especially when you think about David Frankel saying that this to him was about, what does it take to be excellent? Yeah, I think you're right. And I think it was an interesting journey of, for me, this is what I took from the movie.

And I think why I returned to the movie is that I really resonate with not being interested in the ruthlessness required for greatness. And I think that it makes her seem healthy and happy at the end when she steps away from that world. You know, there's a part of her that misses that adrenaline, you know, when she sees Miranda in the street. But ultimately, it was like, it's not worth selling your soul for. And as someone in this industry who's been offered so much in exchange for me to give a lot of myself and make sacrifices, I'm really glad that I didn't. And I've therefore lived a peaceful and happier life than all of my peers pretty much combined. as to how well mentally I feel because I didn't take those steps.

And so I love that it is a film that champions greatness whilst also championing peace and friendship and love and community. You know, I think it does a really good job at showing that both things have their merits. Yeah. And that ultimately picking herself and her sanity and not being a slave to this lunatic woman who doesn't look happy, it really makes the point that having all the money and all the power in the world does not make a happy person. And then we see that when we see Meryl stripped back and crying and her divorce, et cetera.

Beautifully said. All right, Chris, what went right for you? I think the obvious one is Meryl Streep, and maybe we'll leave that to you. But I think the less obvious one, because she was the ninth choice. And I love Emily Blunt in this movie and also just a little plug for your sister's sister, the indie film that I think kind of helped break her out a few years later, Lynn Shelton. And Hathaway is great in this movie. She is great.

And I think it's hard to be the straight man in movies like this. And I think she does a really nice job. She never tries to overpower any of the scenes. She kind of understands her role very well in this type of movie. And she can be very funny. She's very funny in Oceans 8. I didn't love that movie, but I thought she was great in it. She's one of the best parts of it.

Absolutely. And I think she was easy to hate on for a while because people felt like she had this drama camp kid energy to it. I hate that. She just works hard. I do too. I think she's a great actress. And she's also ageless, apparently, as we'll see.

She is doing whatever Tony Goldman's doing, as you mentioned before. But she's really excellent in this movie. And like Rachel McAdams, I think she has a lot of range. And she can do comedy and she can do drama and she can do science fiction and she can do superhero movies. And I was really impressed to hear how much she fought for this role, you know, coming off of something. I mean, she just on Brokeback Mountain. It could have been easy for her to say, like, I just deserve to have something handed to me, which she did. She, you know, that's an Oscar-winning film that she had just done, and she's excellent in it, as Merrill recognized. So I'll give mine to Anne Hathaway.

Perfect. I'm with you 100%. I have never subscribed to the Anne Hathaway hate. I think, honestly, it may have started a bit with that con man boyfriend because there was a bit of the like, well, how could you have not known? And if you look back at some of the articles from the time, there were people saying, well, you know, he was only doing this so he could have money to spend it on Anne Hathaway. And it's just like, fuck you. And then there's the Oscars with James Franco and then Les Mis. And from there, you get this idea that she's sort of a tryhard, to which I say, yeah, she tries. really hard. Is that a bad thing? No, it's not. She's an incredible actress. She works her ass off. I can't wait to see her in The Devil Wars Prada, too. I'm not going to give it to Meryl Streep. She's obviously incredible in this movie, as is Emily Blunt. All the actors are wonderful. I want to give it to Alien Brosh McKenna because having read the book, I think what she is able to do with this adaptation is so impressive. She makes something that is truly inactive. It's just a transcription, really. As Charlie Kaufman would say, Lizzie, in adaptation, it's that sprawling New Yorker shit. It literally is. I can't structure this. It's exactly what the book is, spot on. And she just does

such a good job. And she makes such a tight movie. It's a complicated movie. There's depth to all of these characters. It's funny. Hats off to you, Alien Brosh McKenna. This is a tour to force piece of screenwriting here. So that's who I will give it to. Jamila, thank you. so, so much for being here with us and taking the time to explore. What is truly one of my favorite movies? Yeah. Is there anything that you'd like to plug before you leave? Oh, well, I have a podcast called Wrong Turns with Jamila Jamil. It's very funny. Lots of your favorite comedians in the world come on and tell me terrifying tales that they should have taken to the grave, really, but chose to share with all of us. I will be doing Netflix as a Joke Festival in Los Angeles on May the 4th at 7 p.m. with

Chris Fleming and Lees O'Tregor and Lea Morese. And then I also write a substack called a low desire to please, which I named after my dog when he got his first training card. They said that he's very smart. He just has a low desire to please. And I was like, that is my dog. I birthed him out of my vagina because we must share the same DNA. That's me all the way through. So yeah, so those are the things. And then projects will come out later this year. Amazing. Thank you so much. Thank you for being here. You were so lovely, so generous with your time and everything that you shared. And I really love your podcast. It makes me happy. Thank you. Chris, if people would like to support this podcast, how can they do that? A few very simple ways.

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The Provost family. The O's sound like O's. That's all. Wow. That was cruel, Lizzie. I don't know why you said such. mean things about our most loyal patrons, but it will make them stronger. Excellence is what we demand.

Before we announce what's coming next week, may I offer Lizzie my favorite comp for the budgetary point that Jamila was making at the time? Sure. Talladega Knights, the Ballad of Ricky Bobby. Same year. I really like that movie. It's very silly, very funny. 73 million dollar budget, two times the budget of the Devil Wears Prada.

I would argue roughly equivalent in star power, although not as a is acclaimed dramatically, Will Ferrell is an enormous name, and John C. Riley's an amazing actor. But my point is, it takes place within a specialized world, NASCAR in this instance, very male world, versus more female world, the fashion world. And again, twice the budget, but made half as much at the box office as Devil Wars product. So anyway, that would be my comp. That $100,000 for the costume budget is nuts. And it's crazy. I mean, I get it. I think they thought everybody was just going to lend clothes, but yeah. I think that was probably, they did an initial pass at the budget and they're trying to figure out how to squeeze it into the 35 number that they

have. And they say, well, if we just slash the costume budget by 90% because we assume we can get these for free, then we can get the green light. It's like a weird math you do to try to get something to where it needs to be. By the way, make sure that you come back, not this Friday, but next Friday, because we will be covering the Devil Wears Prada 2 for all of our patrons and bonus subscribers. I'm so excited to watch it. I can't wait to talk about it with you, Chris. So make sure that you come back, not this Friday, but next Friday for that bonus episode. But in the meantime, Chris, what do we have coming up one week from today on Monday? So the Devil Wears Product 2 is going to tee us perfectly into sequel months, as Chris describes it. So for May the Force, not only could you

check out Jamila Jamil's Netflix as a joke performance, you can also tune in for our first sequel of the month, The Empire Strikes Back. We are diving into the dark second entries of a couple of trilogies that we have started on this podcast, and Empire Strikes Back will be the first. Great. All right. We'll see you then. Thanks for listening. Bye.

To support What Went Wrong and gain access to bonus episodes, subscribe on Patreon, Apple, or Spotify for $5 a month. Patreon subscriptions also come with an ad-free RSS feed. You can also visit our website, What Went Wrongpod.com for more info. What Went Wrong is a Sad Boom podcast, presented by Lizzie Bassett and Chris Winterbauer. Post-production and music by David Bowman. This episode was researched by Laura Woods and edited by Karen Krupsaw.