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?
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👋 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
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