The fearless artist and activist, widely recognized for her boundary-pushing work, died just days before returning to the stage.
Jill Sobule, the pioneering singer-songwriter who rose to prominence in the 1990s, died in a house fire early Thursday morning. She was 66.
Her death occurred just ahead of a planned 2025 Colorado tour, with performances scheduled for May 2 in Denver and May 3 in Basalt. Sobule had planned to take the stage Thursday night at Swallow Hill Music’s Tuft Theater in Denver.
That venue will now host an informal gathering in her memory, led by Ron Bostwick of 105.5 The Colorado Sound. Her family and close collaborators are organizing a formal memorial service for later this summer.
Sobule is survived by her brother and sister-in-law, James and Mary Ellen Sobule; her nephews, Ian Matthew and Robert, and Robert’s wife, Irina. She also leaves behind numerous cousins and countless friends.
Ken Hertz, Sobule’s longtime attorney, reflected on their deep personal bond, noting that she was more than a client. He shared memories of her being present for family milestones and even living with them during the pandemic. “She was family to us,” he said.
“Jill Sobule was a force of nature and human rights advocate whose music is woven into our culture. I was having so much fun working with her. I lost a client & a friend today. I hope her music, memory, & legacy continue to live on and inspire others,” said her manager, John Porter.
Her booking agent, Craig Grossman, remarked, “I was fortunate enough to get to know Jill beyond a professional relationship. No one made me laugh more. Her spirit and energy shall be greatly missed within the music community and beyond.”
In the final days of her life, Sobule remained candid and humorous online. In a Facebook post shared at 1:25 a.m. on April 30, she revealed that she was struggling with sciatica while on tour and asked followers for recommendations for doctors and physical therapists in Los Angeles, where she planned to stay for a few weeks.
Despite the discomfort, she kept her tone light, ending the post with a cartoon.
Earlier that same morning, she reflected on her very first professional performance — a small set at a Holiday Inn in Denver decades ago. She recalled the nerves, the modest audience, and the sting of a harsh review from a local music critic. That memory returned after Westword, the outlet behind the original review, reached out for a new interview.
Sobule admitted feeling initial dread, but noted that the recent conversation was “delightful,” adding, “I finally made it.”
In the April 28 Westword profile, she also spoke warmly about returning to Denver, where she grew up. She described visiting her childhood neighborhood of Hilltop and performing an acoustic set of “F*ck 7th Grade” inside her former home.
Former classmates, including some she once called out in song, attended the show. “But it was so great. We’re all friends now,” she said. “It made me realize that everybody was just as miserable as I was.”
She also shared her continued love for the Denver Nuggets, calling herself a lifelong fan and recounting how she once paused a concert to get game score updates from the audience during the team’s 2023 championship run. “I have priorities,” she quipped.
More recently, she debuted a satirical political song while opening for The Fixx in March. She acknowledged it was not radio-friendly, but joked that its message got across clearly. The song gained traction with fans and was sometimes performed casually at her merch booth after shows.
That same sharp wit and willingness to tackle controversial subjects had been part of Sobule’s music from the beginning. She gained national attention in 1995 with her single “I Kissed a Girl,” the first openly gay-themed song to reach the Billboard Top 20. But her influence extended well beyond that cultural milestone.
Over a career spanning three decades and 12 albums, she used sharp humor and candid lyricism to explore themes such as the death penalty, anorexia, reproductive rights, intolerance, and political polarization.
Her work often balanced vulnerability with satire, establishing her as a singular voice in alternative music. She also built strong ties to activists and public figures, earning admiration from both grassroots communities and cultural icons.
Sobule’s most recent creative endeavor was the autobiographical musical “F*ck 7th Grade,” a New York Times Critic’s Pick and Drama Desk-nominated production. It premiered at New York City’s Wild Project Theater in 2022 and returned for multiple runs through 2024.
To honor both her recent and early work, her team will release the original cast recording of “F*ck 7th Grade” on June 6, 2025. That same day, they will also issue a 30th anniversary red vinyl reissue of her 1995 self-titled album, which features both “I Kissed a Girl” and “Supermodel,” the latter widely recognized from the film “Clueless.”
Long before crowdfunding became mainstream, Sobule found innovative ways to connect directly with fans to fund and distribute her work. A regular speaker and performer at TED conferences, she reshaped the artist-audience relationship in the digital age.
Looking back on her career, Sobule was open about the personal detours that shaped her creative output. In a 2018 interview with Billboard, she explained that nearly ten years passed because she kept putting things off. She also went through some difficult personal events, like the death of a parent, a breakup, and moving to a new place.
“I was my own procrastinatrix, is what I call it,” she said, meaning she blamed herself for the delay. But that time away from music helped her reconnect with why she started making it in the first place.
The result was her album Nostalgia Kills. She described it as “a book of short stories,” a collection of songs that reflect on her past. It was produced by Ben Lee and recorded in his Los Angeles home studio, with guest musicians like John Doe, Petra Haden, and Roger Joseph Manning Jr.
Even though the album looks back on her life, Sobule made it clear she didn’t want to get stuck in the past. As she put it, “Nostalgia kills. You’ve got to keep moving or die.”
One song, “I Don’t Wanna Wake Up,” looked ahead instead of back. She said it came from a creative moment while experimenting with music and mindset.
Following the news of Sobule’s death, the entertainment and LGBTQ+ communities were met with another loss.
On April 24, 2025, Jiggly Caliente’s family shared an emotional statement announcing that she had suffered a serious health setback. According to the update, Caliente, born Bianca Castro, had been hospitalized due to a severe infection that ultimately led to the loss of most of her right leg.
At the time, her family explained that her recovery would be extensive and that she would not be appearing in the upcoming season of “RuPaul’s Drag Race Philippines” or participating in public events. They asked fans for privacy and encouraged them to send messages of hope and support as Caliente focused on healing.
Then, just three days later, on April 27, a second statement posted to her official Instagram page confirmed the heartbreaking news that Caliente had passed away. She died peacefully at 4:42 a.m., surrounded by her family and close friends.
The tribute honored her impact on entertainment and advocacy, describing her as a “luminous presence” known for her “infectious energy, fierce wit, and unwavering authenticity.”
The family emphasized that her legacy of love, courage, and light would continue through the countless lives she had touched, promising that her memory would be cherished forever.
Following Caliente’s passing, tributes came pouring in. “RuPaul’s Drag Race” team took to Instagram to share, “We are devastated by the passing of Jiggly Caliente, a cherished member of the Drag Race family.”
The post continued, “Her talent, truth, and impact will never be forgotten, and her legacy will continue to slay — always. We’re holding her family, friends, and fans close in our hearts during this difficult time.”
“Drag Race Philippines” wrote, “We are devastated to hear of the passing of Bianca Castro, aka Jiggly Caliente. Jiggly’s humor, love, and light touched so many in the Drag Race family and beyond. Her legacy will continue to uplift the communities she advocated for.”
“Our love and deepest condolences go out to her family and friends. Please give them the privacy and space to grieve this tremendous loss,” their post concluded.
Fellow Filipina-American “Drag Race” star Manila Luzon also honored Caliente’s legacy, stating in part on Instagram, “I’m really gunna [sic] miss all our long phone calls, your endless barrage of hilarious Reels in my DMs, your cooking, and especially ALL YOUR SHADE!!! 😂”
“Drag Race” judge Michelle Visage added, “My jiggles….The laughter was endless, our talks were special, your energy was contagious. You were and remain so very loved. This world has lost an angel and we want you to soar high…..I love you so much honey @jigglycalienteofficial.”
“Drag Race” season 5 and “All Stars” season winner Jinkx Monsoon’s Instagram tribute read, “Jiggly was so much person in one little body. She lived her life exactly how she wanted to — never taking a moment of it for granted.”
“She always reminded me to be grateful for every little gift our blessed lives give us. She never complained about touring — she loved this life. She accomplished so much in a relatively short time and we are all so proud of her,” Monsoon added.
“She hates it when I sing show tunes, but I got to sing her one last song: there’s no business like show business. […] I love you Jiggly,” the post concluded.
Before she became a trailblazer in drag and LGBTQ+ advocacy, Caliente grew up longing for a world where she could be herself. As a child, she turned towels and blankets into mermaid tails, imagining herself as the iconic Dyesebel.
From an early age, she sensed a disconnect between her outward life and inner truth, often thinking to herself, “This isn’t me.”
Caliente came out to her mother several times — first as bisexual, then as gay, and eventually as a drag queen. It was not until her mid-twenties that she fully expressed her identity, telling her mother, “Ma, I think babae ako talaga,” meaning, “Mom, I think I’m really a woman.” Fortunately, her mother understood and supported her.
Growing up, Caliente learned to stand her ground, developing a tough exterior shaped by personal experiences, including an incident where she defended herself against a bully — an early glimpse of the fierce spirit she would later bring to the stage.
Although she once dreamed of becoming a veterinarian or a comic book artist, studying illustration at the Fashion Institute of Technology, her creativity eventually found a new outlet — the art of drag.
Her journey into drag began in the early 2000s when she attended a local amateur competition at The Web in New York. After her playful critiques from the audience caught the host’s attention, she was invited to compete.
With basic makeup, a red sweater, JNCO jeans, and choreography to Janet Jackson’s “Doesn’t Really Matter,” Caliente delivered a winning performance that would spark the start of her career.
From there, her drive only grew. Inspired by icons like Jackson, Beyoncé, and the Pussycat Dolls, Caliente took the drag scene by storm, entering pageants and competitions across New York.
By 2007 and 2008, she dominated Barracuda’s Star Search, winning an impressive 32 weeks straight — a record-setting streak that cemented her status as a rising star.
Through drag, Caliente not only found fame but also a deeper understanding of her identity. “Drag was the awakening for my transness,” she once said, recognizing that the art form helped her embrace herself fully as a woman.
Caliente’s passing leaves a profound void, but her fearless spirit, groundbreaking artistry, and unwavering authenticity will continue to inspire generations. Her legacy endures in every life she touched and every barrier she helped break.
