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May 21, 2025 55 mins
For many of us who grew up in the the 90s, Julia Stiles was an integral part of our coming of age. Her portrayal of the clever, acerbic Kat in 10 Things I Hate About You was a radical reinvention of the blonde teenage female rom-com lead. Her roles in Save The Last Dance and Mona Lisa Smile spoke to our adolescent feminist awakenings and catapulted Stiles to stardom. And, just like the heroines she played, Stiles chose to do things a bit differently. At the height of her teenage fame, she went to study English at Columbia University, continuing to act throughout her degree, most notably in the first of four Jason Bourne films. Her latest project is her directorial debut - the feature film, Wish You Were Here, which Stiles also produced and co-wrote. As a mother of three, Stiles said that her parenting informed her ability to direct. Wish You Were Here is available now to rent or own on digital platforms. ✨ IN THIS EPISODE: 00:00 Intro 02:08 Directorial Debut: Wish You Were Here 03:40 Balancing Comedy and Drama 08:48 Friendship and Fame 13:39 College Life and Career Choices 21:58 Dancing Through Life 26:03 Landing the Role in Save the Last Dance 26:35 Reflecting on the Audition Scene 27:07 Challenges and Triumphs of Filming 27:50 Looking Back as a Mother and Director 29:48 Directing and Casting Jennifer Gray 31:22 Dancing with the Stars and TikTok Memes 35:56 Body Image and Self-Acceptance 45:30 Meeting Taylor Swift and Final Thoughts Grief, how to stop caring what everyone thinks and discussing the most difficult times in their lives - Elizabeth and Julia answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have something to share of your own? I'd love to hear from you! Click here to get in touch: howtofailpod.com 🌎 Get an exclusive 15% discount on your first Saily data plans! Use code [howtofail] at checkout. Download Saily app or go to to https://saily.com/howtofail ⛵ Production & Post Production Coordinator: Eric Ryan Mix Engineer: Josh Gibbs Studio Engineer: Sam Bair Producer: Hannah Talbot Executive Producer: Carly Maile 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
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