Remembering singer-songwriter Jill Sobule, who performed on Zoom for Streetsblog Chicago’s COVID-era fundraising celebration

On Thursday, I heard the tragic news that groundbreaking singer-songwriter Jill Sobule had passed away at age 66, in a house fire early that morning while she was visiting the Twin Cities. Among many other great folk and pop tunes, she was known for her 1995 hits “I Kissed a Girl,” the first LGBTQ-themed recording to make the Billboard Top 20, and “Supermodel,” which appeared on the soundtrack for the movie “Clueless.” She had been booked to perform in her hometown of Denver on Friday evening, but instead the venue hosted an impromptu memorial.

“Jill Sobule was a force of nature and human rights advocate whose music is woven into our culture,” her manager John Porter said in a statement. “I was having so much fun working with her. I lost a client and a friend today. I hope her music, memory, and legacy continue to live on and inspire others.”

Some Streetsblog Chicago readers may remember that on April 10, 2021, as the COVID-19 pandemic was starting to wind down, Jill played several tunes at our annual fundraising victory celebration, held on Zoom that year. Also appearing at the online party were fellow songsmith and former Windy City resident Meisha Herron, and then-Chicago City Council member / current Chicago Park District chief Carlos Ramirez-Rosa.

So why did Jill Sobule appear at an event hosted by the Chicago region’s sustainable transportation news and advocacy website? I’d been a longtime admirer of her music and had seen her perform live. We became acquainted on Twitter after I quoted her song “Heroes,” about flawed historical figures, in a Chicago Reader article. She graciously accepted my invitation to play at our online event.

As you can see from the video below, she was totally charming and hilarious, and her singing and guitar playing sounded great on Zoom. She even engaged in some stage banter with me.

Here are some highlights from the video:

• 10:35: Carlos Ramirez-Rosa discusses walk/bike/transit and housing issues on Chicago’s Near Northwest Side.

• 26:50: Meisha Herron performs. (Sorry for the poor audio quality – I hadn’t mastered the art of staging Zoom concerts.)

• 39:50: I introduce Jill.

• 41:05: Jill plays a brand new song called “I Don’t Want My Life to Begin,” about the downsides of coming out of COVID lockdown.

• 44:30: She performs her song “Heroes.”

• 47:30: Jill performs her song “I Kissed A Girl.” She notes that it came out 13 years before Katy Perry’s bicurious hit of the same name, and discusses how controversial its release was back then.

• 52:40: She plays “Mexican Wrestler.”

• 59:50: Jill plays “Thank Misery.”

• 104:00: She performs an acoustic snippet of her electric song “Supermodel” for an encore.

I requested “Mexican Wrestler,” a plaintive ballad and, ironically for a sustainable transportation event, her response included a funny anecdote about COVID-era car culture.

“You picked a kind of sad but funny song,” she said. “People ask for this song more than any other song that I play. And it’s also a part of… in May, I was supposed to be doing a show that I wrote with a wonderful playwright [Liza Birkenmeier] called “F*CK7thGRADE.” And it was postponed, but we did three nights at a makeshift drive-in in Pittsburgh, playing to cars, and this song is in there. I couldn’t tell what the cars were feeling when they heard this song. It was very Stephen King-ish. You don’t see anyone. You just see these cars, and they’re honking after a song. But it was kind of great.”

I’d like to offer my condolences to Jill Sobule’s family, friends, and fans. May her memory and songbook be a blessing.

Learn more about Jill’s life at her website.

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