I’ve always prided myself on being the kind of music consumer who purchased music on impulse. When I stumbled across “Things Here Are Different,” Jill Sobule’s 1990 MCA Records debut album on vinyl in a favorite Chicago record store, I bought it without knowing anything about her. This was at a time when we didn’t have our phones in our pockets to search for information about the artist on the internet. The LP stayed in my collection until, as vinyl was falling out of fashion, I replaced it with a CD a few years later.

Early in my career as an entertainment journalist, I received a promo copy of Jill’s eponymous 1995 Atlantic Records album. That year, Atlantic Records was one of the labels at the forefront of signing and heavily promoting queer artists, including Melissa Ferrick and Extra Fancy, and its roster included the self-titled album by Jill. It was a smart move, as the single “I Kissed A Girl” became a hit on radio and its accompanying video (featuring Fabio!) was in heavy rotation on MTV (when they still played videos).

Unfortunately for Jill, she was a victim of record label missteps. When 1997’s wonderful “Happy Town” failed to repeat the success, Atlantic dumped her. That was Atlantic’s loss, because her next album, the superb “Pink Pearl” contained “Heroes” and “Mexican Wrestler,” two of her most beloved songs. Sadly, Beyond Music, the label that released that album ceased to exist after just a few years. To her credit, the savvy Jill had also started independently releasing music (2004’s “The Folk Years”). That was a smart move because her next major-label release, the brilliant “Underdog Victorious” on Artemis Records, met a similar fate when that label folded.

With her 2009 album “California Years,” Jill launched her own indie label, Pinko Records, on which she would release two more outstanding full-length discs, 2014’s “Dottie’s Charms” (on which she collaborated with some of her favorite writers, including David Hadju, Rick Moody, Mary Jo Salter, and Jonathan Lethem), and 2018’s stunning “Nostalgia Kills.” Jill’s cover of the late Warren Zevon’s “Don’t Let Us Get Sick” on “Nostalgia Kills” was particularly poignant as she had toured with him as an opening act.

Jill was a road warrior, constantly on tour, and her live shows were something to behold. My first interview with Jill took place at the Double Door in Chicago in early August of 1995, when she was the opening act for legendary punk band X. She had thrown her back out the previous day and was diagnosed with a herniated disc. To be comfortable, she was lying down on a fabulous-‘50s sofa. “I feel like I’m at my shrink’s,” she said to me, “Do you want me to talk about my mother?”

That sense of humor, which permeated and enriched her music, was one of many reasons to love Jill. I was privileged to interview her for seven of her albums. Everything you would want to know about her was right there in her honest lyrics, in which she balanced her distinctive brand of humor with serious subject matter. Drawing on her life experiences in songs such as “Bitter,” “Underachiever,” “One of These Days,” “Freshman,” “Jetpack,” “Nothing To Prove,” “Forbidden Thoughts of Youth,” “Island of Lost Things,” “Where Do I Begin,” “Almost Great,” and “Big Shoes,” made her songs as personal as they were universal, elicited genuine affection and concern from her devoted fans.

While she was a consummate songwriter, Jill also felt equally comfortable covering songs made famous by others, including “Just A Little Lovin’” (on the 2000 Dusty Springfield tribute album “Forever Dusty”) and “Stoned Soul Picnic” (from the 1997 Laura Nyro tribute album “Time and Love”). Jill also didn’t shy away from political subject matter in her music with “Resistance Song,” “Soldiers of Christ,” “Attic,” “Heroes,” “Under the Disco Ball,” and the incredible “America Back” as prime examples.

Here’s something else worth mentioning about Jill. She was known for collaboration skills. As a songwriter, she maintained a multi-year creative partnership with Robin Eaton (“I Kissed A Girl” and many others), as well as Richard Barone, the gay frontman of the renowned band The Bongos. Jill’s history with Barone includes performing together at a queer Octoberfest event in Chicago in 1996. Writer and comedian Julie Sweeney, of “SNL” and “Work in Progress” fame was another Chicago collaborator with Sobule (Sweeney lives in a Chicago suburb), where they frequently performed their delightful “The Jill and Julia Show.” John Doe, of the aforementioned band X, also collaborated with Jill in the studio (“Tomorrow Is Breaking” from “Nostalgia Kills”), as well as in live performances.

On a very personal note, in 2019, when I was in the process of arranging a reading at the fabulous NYC gay bookstore Bureau of General Services – Queer Division, I reached out to Jill and asked her if she would like to be on the bill with me. We alternated performing; I would read a couple of poems, and Jill would sing a couple of songs. She even set one of my poems to music, on the spot.

Jill had an abundance of talent, and when she turned her attention to musical theater, it paid off in a big way. Her stage musical “F*ck 7th Grade,” a theatrical piece that seemed like the next logical step in her career, had its premiere at Pittsburgh’s City Theatre in the fall of 2020, during the height of the pandemic. The unique staging (an outdoor drive-in stage at which audience members watched from their cars) was truly inspired. “F*ck 7th Grade” went on to become a New York Times Critic’s pick, as well as earning a Drama Desk nomination.

In honor of the 30th anniversary of Jill’s eponymous 1995 album, reissue label Rhino Records is re-releasing it on red vinyl. Jill and I had been emailing each other to arrange a time for an interview. We even had a date on the books for the third week of May.

When she died in a house fire in Minnesota on May 1 at age 66, Jill received mentions on network and cable news shows. She was showered with attention from major news outlets, including obits in the New York Times and Rolling Stone (but not Pitchfork, who couldn’t be bothered to review her music when she was alive). Is it wrong to think that if she’d gotten this much attention when she was alive she could have been as big as Taylor Swift? I don’t think so.