Episode 74: Jill Sobule

Over the course of her nearly forty-year career, singer-songwriter Jill Sobule has earned a singular spot in the American songbook. Best known for her breakout 1995 singles “Supermodel” (from the “Clueless” soundtrack) and “I Kissed a Girl” (which came out more than 10 years before the Katy Perry hit of the same name), her quirky, heartfelt, cheer-filled songs are difficult to categorize: she sings about the death penalty, anorexia, shoplifting, the French Resistance, LGBTQ issues and Mexican wrestling. 

In another decade, Jon Pareles, the chief pop music critic of The New York Times, wrote that she stands “among the stellar New York singer-songwriters of the last decade”—high praise that has surely applied in all subsequent decades.     

Jill’s songs are enchanting, disarmingly funny and achingly poignant, and many of them are featured in her Drama Desk-nominated autobiographical musical "F*ck 7^th Grade," which premiered at the Wild Project in NYC in 2022 and returns for a limited engagement in November 2024. 

“We didn’t have to create a story around these songs,” she says of the show, which she really, really hopes isn’t dismissed as just another jukebox musical featuring songs from an artist’s back catalogue. “These songs are my story. I just wrote a few more to fill out the narrative.”

Jill joins us on the podcast to discuss her rich and varied career as one of the music industry’s most uniquely collaborative artists. She’s performed with musicians such as Neil Young, Billy Bragg, Steve Earle, Cyndi Lauper, and Warren Zevon, and once released a concept album of original music with lyrics written by some of her favorite writers, including Jonathan Lethem, Rick Moody, Mary Jo Salter, Vendela Vida, and David Hajdu. She regularly tours with comedian/actress/author Julia Sweeney in their two-woman “Jill & Julia” show.

Two highlights from the very many cool, pinch me-type moments that have stamped Jill Sobule’s remarkable career: she inducted Neil Diamond into the Songwriter’s Hall of Fame, and she appeared as herself on an episode of “The Simpsons.”  So, you know, there’s that. 

Learn more about Jill Sobule:

• Website
• Patreon
• Instagram
• Threads
• Facebook
• Twitter

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