Julia Stiles on Fame, Feminism & Finding Her Voice Behind the Camera

If you grew up in the '90s, Julia Stiles was more than just a movie star—she was part of your personal coming-of-age story. Her sharp, unforgettable performance as Kat in 10 Things I Hate About You flipped the rom-com blonde stereotype on its head. Roles in Save The Last Dance and Mona Lisa Smile spoke directly to a generation of budding feminists, cementing her place in Hollywood’s cultural memory. But Julia never played by the usual rules. At the height of her fame, she enrolled at Columbia University to study English—balancing life as a student while appearing in the first of four Jason Bourne films. Now, she's behind the camera for the first time. Her feature film Wish You Were Here—which she directed, co-wrote, and produced—is deeply personal. As a mother of three, Julia says her parenting shaped how she leads on set. Wish You Were Here is available now to rent or own on digital platforms. This isn’t just a debut—it’s a bold new chapter. 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 Subscribe to unlock more episodes: https://howtofail.supportingcast.fm/#... Get in touch: https://howtofailpod.com How to Fail is a Sony Music Entertainment & Elizabeth Day production. Find more great shows from Sony: https://sonymusic.com/podcasts To advertise: podcastadsales@sonymusic.com Ad Choices: https://podcastchoices.com/adchoices Use code howtofail for 15% off your first Saily data plan: https://saily.com/howtofail #JuliaStiles #HowToFail #ElizabethDay #10ThingsIHateAboutYou #SaveTheLastDance #WishYouWereHere #DirectorialDebut #Grief #PodcastInterview #SonyMusicPodcasts #FailingWithFriends #WomenInFilm #BookToFilm #PodcastClips