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

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

Author: Elizabeth Day and Sony Music Entertainment May 6, 2026 Duration: 51:21
How To Fail With Elizabeth Day
SocietySociety & CultureCulture
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

There's a quiet revolution happening in how we think about success, and How To Fail With Elizabeth Day is right at the heart of it. This isn't about schadenfreude or wallowing in misfortune. Instead, Elizabeth Day has created a space where the most interesting conversations begin with a simple, radical premise: our lowest moments are often our greatest teachers. Each episode, a guest-from celebrated artists and thinkers to everyday people with extraordinary stories-sits down to examine three significant failures from their own life. The magic lies in the excavation, as Elizabeth guides the discussion toward the unexpected wisdom and resilience that emerged from those setbacks. You'll hear the raw honesty in their voices, the laughter that comes with hindsight, and the profound clarity that failure can uniquely provide. This podcast, presented by Elizabeth Day and Sony Music Entertainment, digs into the messy, human stuff of life that connects us all, transforming shared vulnerability into a source of collective strength. It’s a reminder that the path to any meaningful achievement is rarely a straight line, but a series of instructive detours. The show actively invites listeners to reflect on their own stories, fostering a genuine community around the idea that we can all succeed better by understanding where we've previously stumbled. Tune in for conversations that are as comforting as they are challenging, and which might just change your perspective on what it means to live a well-lived life.
Author: Language: English Episodes: 50

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How To Fail With Elizabeth Day
Podcast Episodes
ON FAMILY DYNAMICS… With Bella Freud and Danny Dyer [not-audio_url] [/not-audio_url]

Duration: 21:48
Families are fascinating: how those first bonds shape our understanding of love, security and ourselves. In this episode, we revisit episodes with Bella Freud and Danny Dyer, who each open up about the simultaneous beaut…
Mo Gilligan - Fatherhood Is A Gift I Didn’t Know I Needed [not-audio_url] [/not-audio_url]

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Mo Gilligan started out working in retail (think Jo Malone and Levi’s) but quit in 2018 when his online comedy videos went viral. The leap paid off - sell-out tours across the UK, a late-night entertainment show on Chann…
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Duration: 28:20
We’re taught that love should happen early, and if it doesn’t, something’s gone wrong. But what if that’s not true? In this episode, we hear from past How to Fail guests who found love later, or in their own time. Luke E…
Shabaz Ali - ‘I’ll be a diversity quota as long as I get paid’ [not-audio_url] [/not-audio_url]

Duration: 49:02
A few years ago, Shabaz Ali was a chemistry teacher in Blackburn. Today, he’s one of the internet’s most beloved creators, best known as Shabaz Says, with millions of fans and a knack for skewering the most outrageous (a…
ON FINDING HOPE IN ADVERSITY… With Sir Chris Hoy and Michael Rosen [not-audio_url] [/not-audio_url]

Duration: 19:44
This week we’re revisiting two deeply moving conversations that explore what it means to find hope in the face of profound adversity. First, we hear from the 11-time world champion and a six-time Olympic champion, Sir Ch…
ON THE IMPACT OF EARLY FAME… With Shania Twain and Charlotte Church [not-audio_url] [/not-audio_url]

Duration: 32:09
Fame isn’t always limousines, five star hotels, champagne and private jets. I find this topic totally fascinating and these two past How to Fail guests give us a glimpse behind the curtain as to what becoming famous at a…
Martin Freeman - ‘We should be saying no to our kids’ [not-audio_url] [/not-audio_url]

Duration: 53:44
Martin Freeman is one of the most sought-after actors of his generation. Whether it’s Tim in The Office, John - the mild-mannered porn actor in Love Actually, Watson in Sherlock, Bilbo in The Hobbit, the stressed parent…
ON PANIC ATTACKS… With Jamie Laing and Fearne Cotton [not-audio_url] [/not-audio_url]

Duration: 16:51
Panic attacks are wide-spread in today’s society, and yet remain something we rarely talk about openly. So it’s vital that we normalise an experience so many of us share - because talking about it is often the first step…

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