Mr Viral
On May 1, 2025, the singer-songwriter world lost one of its most irrepressible and beloved free spirits when Jill Sobule died in a house fire while on tour in Minnesota.
Sobule, 66, was best known, in her own words, as a “two-hit wonder”: for “I Kissed a Girl,” from 1995, the first overtly gay-themed song to reach the Top 20 (13 years before Katy Perry’s song of the same title); and “Supermodel,” featured in the Clueless movie soundtrack. But those were just a tiny taste of Sobule’s catalog of superb folk-pop-rock songs—packed with offbeat storylines, mischievous humor, and killer hooks. Along the way in her 35-year career, she was also a pioneer in the music industry she sometimes satirized, as one of the early independent artists to crowdfund an album release.
Growing up in Denver, Sobule had diverse inspirations, from the Beatles to Sly Stone to John Prine. When I interviewed her for Acoustic Guitar in 1997, just after she released Happy Town, she described her songs as rooted in storytelling. “I write like I’m writing a story,” she said. “I always start with verses, where a lot of people begin with, ‘OK, I’ve got a really good hook, and let’s figure out how we can use this hook.’ [For me] the chorus is usually the last thing. It’s more narrative.”
Sobule’s songs introduced all sorts of vivid characters, such as the seemingly conservative shoe store manager who turns into a leather-clad biker after hours in “Karen by Night,” the overlooked dreamer struggling through school days in “Underachiever,” or the aspiring actor posing as a superhero for tips on the streets of Hollywood in “Spiderman.” No one wrote more authentically and movingly about the misfits and outcasts of adolescence than Sobule. She ultimately turned a body of songs about middle school into an autobiographical musical, F*ck 7th Grade, that premiered in New York City in 2022. (Listen to a sampling of her songs in this playlist.)
Along with her songwriting gifts, Sobule was an inventive and distinctive guitarist. On her folkier acoustic side, she employed what she called “weirdo chords” in her songs, performing primarily with a Vagabond travel guitar—luthier Kevin Smith created a signature model in her honor. She initially discovered this diminutive instrument in the ’90s while recovering from back surgery but grew attached to its unique attributes. “I’ll be doing these songwriters’ shows where you’ve got a guy with a Martin from the ’40s and all these other nice guitars, and here I am with my little $400 Vagabond guitar through the Demeter [preamp], and people are going, ‘How do you get that sound?’” she told me. “It’s really worked well for me. Plus, I like it not looking like a guitar. It looks like some kind of lute.”
On electric guitar—often a Gretsch—Sobule played raucous, exuberant solos on “I Kissed a Girl” and many other songs. “I have no clue what I’m doing, so I go for noise,” she said. “And I can’t have a guitar without a whammy bar. It’s my own style and I don’t know where it came from, but it came late in life when I hadn’t played electric in ages.”
Sobule brought the same playful, experimental spirit to the business of music. In 2009, having been through the wringer in the record industry, she enlisted her devoted fan base and raised more than $85,000 to fund California Years, produced by Don Was and released on her own Pinko Records label. Her website Jill’s Next Record offered a range of donation levels, from Unpolished Rock to Weapons-Grade Plutonium, with perks like downloads, house concerts, and custom theme songs. For the Gold level, donors were named in the closing track, and Gold Doubloons, she noted, was “exactly like the Gold level, but you give me more money.” The founders of the not-yet-launched site Kickstarter took note, contacting Sobule to pick her brain about her witty and personal approach to fundraising.
Throughout her career, Sobule maintained an unusually close relationship and correspondence with her audience. In 2009, for an AG article about California Years, she told me, “I wanted this to be as close a connection as possible and have people participate, because I put people who follow me up on a pedestal in a way—God, they’re the ones who have kept me afloat and not having a real job—and I actually think they’re really smart.” She even asked supporters to give feedback on the mixes and help pick the final track list.
Well before the news came of Sobule’s sudden passing, two releases were planned for June 6: an original cast album of F*ck 7th Grade and a 30th anniversary reissue of her breakthrough self-titled album. One single from the cast album has dropped: a new take on her early song “Underdog Victorious,” which tells the story of Bobby Trucks, “a fat little boy living in a shitty little town.” She sings, “Every recess the dodgeball flew/ And knocked poor Bobby down.” Then comes the quintessential Sobule twist.
Four o’clock when he got home
Upstairs in his room
He’d close the door
Tie on his cape
Put on his skin-tight suit
And he’d sing
Underdog victorious
He was simply glorious
Someday he’d die notorious
Underdog victorious
At the time of her death, Sobule was about to return to her hometown of Denver to perform songs from F*ck 7th Grade, and she had a packed tour schedule around the country through the year. Several upcoming concert dates are being turned into tribute events called Jillith Fairs, with her many admirers and collaborators gathering to celebrate her songs and spirit.
While Sobule never matched the commercial peak of her ’90s hits, she continued for another three decades to achieve the ultimate artistic success: unapologetically being herself—and encouraging others to do the same. That legacy and gift, no doubt, will live on.
