Sobule made her debut in 1990 with the Todd Rundgren-produced Things Here Are Different. Unfortunately, nobody bought it and Sobule briefly left music to work for a wedding photographer. A few years later, she was picked up by Atlantic Records for the release of her self-titled second album, which featured the hits "I Kissed A Girl" and "Supermodel," the latter of which was famously used in the Brittney Murphey film Clueless. Her follow up, Happy Town, earned rave reviews, but didn't repeat the commercial success of her previous album and she was dropped from the label.
Despite her 15 Minutes of Fame passing rather quickly, Sobule has kept busy ever since, recording and releasing music independently, joining Lloyd Cole's backing band, done some acting and contributed songs to the Nickcom Unfabulous and the Off-Broadway production Prozak and Platypus.
"I kissed a trope!"
- Broken Pedestal: The concept of "Heroes" is about how so many artistic and social ground-breakers were imperfect in increasingly problematic ways.
- Concept Album: Dottie's Charms was inspired by a charm bracelet Jill had been given which her friend had found in a thrift store. She made up stories about who the previous owner had been and collaborated with a different writers for each song based on a different charm. She later joked that the only thing she knew for certain about Dottie was "she had shitty kids who sold her charm bracelet."
- Cool Old Lady: The titular Claire in "Claire," a former WWII fighter pilot who may or may not have had an affair with Eleanore Roosevelt and is now a senile old lady. The narrator sings about how she wishes she could find out how many of Claire's stories were true.
- Cover Version: She's done several, including "All The Young Dudes" by Mott the Hoople, "Merry Christmas From The Family" by Robert Earl Keen, "Christmastime Is Here" from A Charlie Brown Christmas, "Never My Love" by The Association and "This Land Is Your Land" by Woody Guthrie.
- Downer Ending: "Lucy At The Gym." After a perceived several months of nonstop working out and starving herself to get a perfect body, the titular Lucy stops showing up at the gym and the narrator concludes that she literally worked herself to death. Also counts as Write What You Know, as Sobule struggled with anorexia for many years.
- Gag Nose: Downplayed. Her substantial nose is easily one of her most visually recognizable assets, but doesn't get called attention to much.
- Girl on Girl Is Hot: "I Kissed A Girl," a spoof on the "Lesbian chic" trend of the '90s.
- Intergenerational Friendship: She was good friends with Warren Zevon in his later years. The two of them bonded over having their only big hits be fluke novelty songs.
- Lonely Piano Piece: "Lonely Eighty Eight" is this trope to it's logical extreme: it's a lonely piano piece about pianos and being lonely.
- Masked Luchador: "Mexican Wrestler":"Sometimes I wish I was a wrestler
A Mexican wrestler in a red vinyl mask
I would pick you up and body slam you
And possibly cause you physical harm"
- Naughty by Night: The appropriately-titled "Karen By Night."
- Protest Song: "When They Say We Want Our America Back" and "Givin' it To The Dems."
- Sampling: "Cinnamon Park" is based around a loop of the hook from "Saturday In The Park" by Chicago.
- Self-Titled Album: Her second one and the first of two she recorded for Atlantic.
- Take That!
- As mentioned above, "I Kissed A Girl" is meant to call out the perceived chicness of lesbianism in the '90s.
- "When They Say We Want Our America Back" is a scathing attack on latent white supremacy.
- "Givin' It To The Dems" is a scathing attack on how conservatives are more obsessed with pissing off liberals, to the point of being Too Dumb to Live, than doing anything of benefit to themselves or their country.