I was scrolling my Insta on May 1st when I saw my favorite human and Go-Go, Jane Weidlin post in grief that it did not feel real. What didn’t feel real? Jill Sobule passed at age 66. I felt the breath escape my lungs and a wave of emotion hit. She’s one of those icons I had a brief moment in life with that was sublime.
As a singer-songwriter she spent three decades using music as a mirror for society’s hopes and flaws. Best known to many for her cheeky song (that has nothing to do with Katy Perry) “I Kissed a Girl,” Jill built a career rich with wit, candor, and social commentary that went far beyond that one moment of pop fame.
As dedicated fans and fellow artists mourn her I wanted to take a moment to celebrate a pioneering voice that was as fearless as she was heartfelt. I need my readers to know how amazing and important she was. And to her core fans and her dear friends, I know this will be surface on some levels, but I need you to know that I approached this with tenderness, respect, and care. How the hell do you talk about someone this amazing and not write a 300 page biography? You can’t. You do your best.
A Trailblazer in Socially Conscious Pop and Folk-Rock
Jill Sobule was a trailblazer who re-shaped socially conscious music. Her 1995 breakout “I Kissed a Girl” wasn’t just a catchy tune, it was a groundbreaking same-sex anthem that broke into the Billboard Top 20. That did not happen in 1995. Being openly LGBTQIA+ was a career killer.
It was widely regarded as the first openly lesbian pop song to achieve that milestone. In an era when such themes were unheard of in mainstream music, Jill’s wry, tongue-in-cheek storytelling about a woman’s unexpected experience struck a chord. “I Kissed a Girl” opened doors for future LGBTQIA+ pop stars to be more open about their identity in song. She often said she was proud of the impact it had: “Not because of sales and not for it being on MTV but because of what it did for people. That feels like a success.”
But her influence ran deeper than any chart position. That same year, she also scored the satirical hit “Supermodel,” a fuck you to beauty standards that was featured in the film Clueless. As a child model that one hit me in a dark place that needed to be hit.
Together, those songs showcased Jill’s signature approach: folk-pop melodies paired with sharp social commentary and sly humor.
Throughout the 1990s and 2000s, she released album after album at a breathless pace covering topics many pop artists wouldn’t… or couldn’t… touch! Anorexia, capital punishment, reproductive rights, Christian nationalism, and so much more. She had this beautiful gift for wrapping serious subject matter in disarming satire, engaging listeners who might not otherwise confront these issues.
Jill also pioneered new paths for independent musicians. When major labels dropped her, Sobule took matters into her own hands and became an early adopter of crowdfunding in music. In 2008, long before Kickstarter and crowdfunding was commonplace, she appealed directly to her fans to finance her album California Years. She raised nearly $90,000 and proved that an authentic artist could survive and thrive with the support of a loyal community.
This bad ass move that did not need corporate men in suits. Alongside her next crowd-funded album Nostalgia Kills, Jill became a beacon that breathed new life into DIY musicians navigating a changing industry. An industry creatives and fans forged and suits fuck up.
As she put it, she loved taking a swing at “the old paradigm” of the music business. Sobule’s independent spirit inspired countless younger singer-songwriters to forge their own paths outside the broken system that the music industry has become.
In recent years she turned her own teenage experiences into an off-Broadway autobiographical musical! “F*ck 7th Grade.” It landed in 2022 to critical praise, the show explored the confusion, humor, and hurt of adolescence. Including Jill’s memories of being a tomboy with secret crushes on her female friends. It was yet another example of how she used storytelling to shine a light on identity and growth. She was taking the stage to remind new generations that feeling like a misfit can be the start of finding your true self. As one reviewer noted, her songwriting always lent a “unique LGBTQ+ lens to the coming-of-age story” that few artists of her time voiced so openly.
Mourning a Voice of Candor and Wit
News of Jill Sobule’s death has prompted an outpouring of tributes from fellow musicians, friends, and fans at a level of intimacy and grief I have never seen in the wake of an artist’s passing. All testifying to her deep contributions and the void she leaves behind.
“Jill Sobule was a force of nature whose music is woven into our culture,” wrote her longtime manager John Porter, who called her passing both a professional and personal loss: “I lost a client and a friend today. I hope her music, memory and legacy continue to live on and inspire others.” His words were echoed by many who worked with her.
Her booking agent, Craig Grossman, lauded not only her talent but her generosity and humor, saying “she was such a force of nature… very, very funny. If you saw her live, you became a friend – she was very, very accessible.” Grossman recalled how she could even turn controversy into comedy onstage. During a recent tour with the 1980s band The Fixx, Jill debuted a song titled “You Better not F*ck in Texas.” It is a pointed protest against draconian anti-abortion laws.
Provocative, bold, and warm-hearted: that was Jill.
The artists and friends who knew her best are struggling to imagine a world without her light. Comedian Margaret Cho, a close friend who once directed one of Sobule’s music videos, expressed disbelief at the news that wrecked me to read. “This is not real to me… I am in shock and cannot process this,” Cho wrote, capturing the heartbreak many felt.
Actress and writer Sarah Thyre, who collaborated with Jill on a podcast project, reflected on how reliably and passionately Jill gave of herself: “Jill Sobule was an amazing, generous artist who lent her time and talent to abortion rights and other progressive causes. She ALWAYS showed up and showed out,” Thyre wrote on Instagram. Beyond her activism, it was Jill’s personality that endeared her to so many. “Above all, she was just lovely and playful and earnest and talented,” Thyre added, before noting the significance of Sobule’s biggest hit: “Her song ‘I Kissed a Girl’ blew the doors open for queer folk.”
Meanwhile, Sobule’s recent tourmates in The Fixx posted their own homage, mourning the loss of a comrade taken far too soon. “We are absolutely devastated and shocked to hear the news of Jill Sobule’s untimely passing… she was so full of life and talent. Our hearts are broken. We will always miss her,” the band wrote.
Fans in her hometown of Denver gathered at what was to have been a concert venue for her show, turning it into an beautiful and raw impromptu memorial where her songs played on in tribute.
I promise you, I have barely scraped the surface of the dedications to her and her legacy. From social media remembrances to candlelight gatherings, the message is clear: Jill Sobule touched countless lives with her music and spirit, and her loss is being felt around the world.
Why Her Voice Mattered: On Gender, Identity, and Cultural Wit
Jill Sobule’s death isn’t just the loss of a beloved singer-songwriter; it’s a broader cultural loss of a voice that fucking mattered. In the 1990s, pop music didn’t foreground the experiences of young women grappling with identity, or celebrate queer desire. Jill did both. At a time when the music industry was still uneasy in their cowardice about open LGBTQIA+ themes she chose to sing her truth, and the truth of countless others. She carved out a space for conversations about gender and identity in pop culture well ahead of the curve.
Jill penned tunes over the years about everything from the death penalty to environmental collapse, always colored with empathy and insight. She spoke up about her own struggles too! She had songs that spoke to depression and anorexia in her youth. Her entire catalog feels like an ongoing conversation about the human condition, seen through a uniquely queer feminist and humorous lens with one clear message for others. You are not alone!
Authenticity, Fragile Icons, and Generational Resilience
In reflecting on Jill Sobule’s legacy, I can’t help but wonder how much of her inspiration is in my book, Hearts of Glass: Living in the Real World. I wanted to write not just a coming-of-age tale, but I wanted to examine the search for authenticity, fragility, and the resilience that defines youth and life in the margins.
Jill’s life embodies each of these ideas. Authenticity was her guiding star. She refused to fit into the music industry’s prefabricated boxes, choosing instead to write the songs she needed to write and to engage with her fans on her own honest terms. It’s the same kind of authenticity that drives so much of what I try to do. I have always been drawn to artists who refuse to settle or look away in a world full of compromise. Jill Sobule never looked away.
At the same time, her sudden death underscores the fragility of life. For many Gen Xers and older Millennials, she was an icon. To lose her so unexpectedly is to be reminded that even our cultural heroes are mortal, and the nostalgic ideals we treasure can be heartbreakingly vulnerable. A heart of glass can shatter. Yet, in shattering, it reflects light. The flood of memories and tributes we’ve seen for Jill Sobule shows how an artist’s influence, though delicate, can shine on brightly through others.
Finally, there is generational resilience that fights generational trauma. Jill Sobule’s generation has weathered immense changes, from the analog simplicity of the ’80s and ’90s to the hyper-connected complexity of today. Artists like Sobule taught us how to adapt without losing ourselves. When the system failed her, as it has so many, she adapted by reaching out directly to her community.
In the wake of marginalization we need examples that adapt, endure, and find ways to thrive in the cracks of a broken world. Jill Sobule did exactly that. She found ways to keep making music and meaning in the cracks of a broken music industry. That resilience is something survivors learn well. We take the bittersweet, the tragic, and the absurd and keep moving forward with hope intact despite the horrors of life with goddesses like her guiding us..
As we say goodbye to Jill Sobule, I hope we carry forward the authenticity and courage she exemplified in these dire times. Her legacy is a mosaic of catchy tunes and bold truths, each song a small act of rebellion against apathy or conformity. Yes, our hearts are broken by her loss. But it is my hope that we’ll mend those cracks with humor, with honesty, and with the music she left us. In celebrating Jill Sobule’s life, we can reaffirm what she always stood for: being true to oneself, speaking out for what’s right, and finding connection through the stories we share.
That, in the end, may be her greatest gift to all of us. A reminder that living in the real world is easier when we do it with open hearts, a fearless voice, and a few great songs to get us through it all.
Stay totally awesome!
Stay True to you!
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