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

How To Fail With Elizabeth Day

Sony Music

Society & Culture

4.7 • 9.6K Ratings

🗓️ 6 May 2026

⏱️ 56 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	It doesn't take a genius to figure this out.
0:01.4	The minute we cast Merrill, I thought, oh, this could be awesome.
0:05.3	At the end of the class, he said, I've never said this to anyone in seven years, but you need to move to L.A. and be a screenwriter. This is what you were meant to do. Here's when I knew it was not going to work. We shot it, and the executive comes up to me, and she goes, You know, whatever happens with this, this thing is a real feather in your cap.
0:22.6	And I thought, oh, we're doomed. comes up to me and she goes, you know, whatever happens with this, this thing is a real feather
0:21.2	in your cap. And I thought, oh, we're doomed. Welcome to How to Fail, the podcast that believes that
0:27.6	sometimes the message is in the mess. Before we get into this conversation, please do remember to
0:33.6	like, subscribe and follow so that you never miss a single episode.
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