Every three or four years or so, singer Jill Sobule rewatches Clueless, always at the urging of a friend. "I’m like, 'I don’t want to watch it,'" she tells Refinery29 over the phone from California where the resident New Yorker has been trapped since the coronavirus pandemic started. "But then I’m always excited to watch it."
Twenty-five years after Clueless hit theaters, Sobule, like many others, can't seem to quit the satirical adaptation of Jane Austen's Emma that turns the titular character into a privileged Beverly Hills teen whose "main thrill in life," according to her bestie Dionne (Stacey Dash), is giving makeovers. However, knowing Sobule is the woman behind "Supermodel," the song which soundtracks the now legendary makeover Cher (Alicia Silverstone) gives new girl Tai (Brittany Murphy), you can understand her apprehension to press play. For her, every rewatch is a walk down memory lane. It's only in the past few years that Sobule realized, those who grew up with the rom-com feel the same way.
"There are those songs you can’t get over. The songs you hear between that age of 10 and 17 that imprint in your brain forever," she says. "I think that ‘Supermodel’ is one of those songs for some girls. And it's a fun little part of my legacy."
Sobule hasn't always felt so warm and fuzzy towards her second hit after "I Kissed A Girl," a subversive queer anthem that charted 13 years before Katy Perry sang those same words. ("On social media, someone will be nasty and go, 'Oh she’s a one-hit wonder,'" she says. "I love to go, 'Excuse me sir, I was a two hit wonder!") In honor of the 25th anniversary of Clueless, Sobule is once again reminiscing about the effects the song had on her career and, for the first time, talking about the one thing she wishes she had done differently.
Sobule doesn't know if she was the first singer Clueless's music supervisor Karyn Rachtman considered for "Supermodel," but she understands why she might have been. "I feel like they came to me because it had a satirical point of view," she says, a staple of her songwriting then and now. "It would have been different if it sounded like a Celine Dion song."
The track, written by David Baerwald, David Kitay, Brian MacLeod, and Kristen Vigard, was intended to sound like it came out of the mouths of teenage girls. Baerwald turned to the teen magazine Sassy for help, lifting lines from the letters to the editor to make it feel more authentic. Sobule's voice did the rest. "Even though I was much older than a teenager at the time, I think [my voice] had a kind of young adult novel energy to it," says Sobule, who was 34 then. However, Sobule never considered the song to be from Cher's POV, she sang it as if she was a girl on the outside looking in, wishing she could be part of the popular crowd. "I loved the girls in Clueless, but I would have been the weird goth girl or something," she jokes.
Despite her initial reservations over recording a song she didn't write, "I wanted to put my own strange thumbprint on it," she says. Sobule's prints are all over the whammy-heavy guitar solo and lyrics that referenced her past struggles with an eating disorder. On the song's bridge, Sobule lowers her voice to a near whisper and sneers, "I didn't eat yesterday/ I'm not gonna eat today/ I'm not gonna eat tomorrow/ Cause I'm gonna be a supermodel."
Then, as now, it's hard not to hear those lyrics and think Sobule is making light of the pernicious "heroin chic" trend that filled the fashion magazines of the era. While her delivery may have been "barbed," she says that was never her intention. Nor did she intend to inadvertently send a pro-anorexia message with the track. (A criticism that was later aimed at another Sobule song, "Lucy At The Gym," about a woman who exercises excessively to lose weight.) She says she wrote the bridge as a way to shine a light on the beauty-industrial complex and its effect on young women. "I was a person, who in high school, had an eating disorder," she explains. "So to me, 'I wannabe a supermodel,' had meaning beyond the satire and silliness."
Those lyrics continue to rub many listeners the wrong way, but Sobule still regrets not getting involved in the discussions over the song's writing credits. "I think there was something that bugged me when it first came out, just a little bit," she says of not being properly credited. "It doesn’t bother me now, but I think it was kind of shitty and I don’t know if I’ve ever said that."
"I wish I would have been more proactive and talked to the writers directly," she says. To her credit, being a woman in music in the '90s did not often come with authority. "I felt so overwhelmed at that time and remember thinking, 'Well, they must know better,'" she says. "[I] didn’t want to be trouble."
For Sobule, working with a major label required a bit of compromise. Her self-titled record featuring "Supermodel" came out on Lava Records in 1995 and Capitol Records released the Clueless soundtrack the same year; both were under the Universal Music Group umbrella. While she didn't push for a "Supermodel" writing credit, she did fight for control of the song's video, a send-up of another teen movie, Carrie.
In it, Sobule wears a crimson babydoll shirt dress. Her eyes, rimmed in heavy black kohl, look like a raccoon's and her bleached blonde curls give her a Shirley Temple as riot grrrl feel. The only connection the video has to its source material is its opening: The early Clueless scene in which Cher walks down her school's hallway talking to Di on her cellphone before ending up right next to her. "I'll call you, okay?" Cher says as they both head to their next class.
In hindsight, Sobule admits not tying the song's video to the movie might have been a mistake. "They were so unhappy at the label," that she didn't lean into the movie's now iconic fashion. "It made me question myself," she says. "Now it’s like, 'Man, I look fierce.' I wish I was that person more, you know?"
Still, being the woman who sang "Supermodel" had lasting effects on her career. On the 20th anniversary of Clueless, Rachtman went so far as to say the song "might have been the death of [Sobule's] career. Her first song, 'I Kissed a Girl,' was a novelty song, and then this song kind of had a novelty feel to it."
Sobule agrees. "I have not always made the best business decisions."
While she loved pop music, she was always a little too weird for the mainstream. "Supermodel" and "I Kissed A Girl" were alt rock hits, but they were outliers in her discography. "I think that’s why on the next record" — 1997's Happy Town — "I decided to do pretty dark songs," she says. "And then [my record label] was like, 'I really don’t know what to do with you now.'" When she abandoned the novelty song circuit, they dropped her.
In the years since Clueless, she recorded 10 studio albums, finding an alternative to the major label system by crowdfunding her 2009 album, California Years — a year before Kickstarter launched. (She says the founder of Kickstarter reached out to her for tips.) Sobule wrote music for movies and TV including Nickelodeon's Unfabulous and is now working in the theater world. Amid the pandemic, she's figuring out how to stage her one-woman show Fuck 7th Grade, which, according to Sobule, "is very Clueless." Those things all came because of, or perhaps, in spite of "Supermodel," and 25 years later, she finds no shame in that.
"I look at 'Supermodel' and sometimes I think, 'Well, maybe I could have been more successful if I would have made different choices. If I would have done this or done that,'" she says. "And now I look at it and say, 'You know what, it’s all fucking great.'"