The Clueless Soundtrack Is Turning 20

Clueless is now officially a classic—at least in Cher Horowitz’s worldview. The film is celebrating its 20th anniversary, but it doesn’t look a day out of high school.

Written and directed by Amy Heckerling, who also brought the world Fast Times at Ridgemont High, Clueless made stars out of actors like Alicia Silverstone, Paul Rudd and Brittany Murphy. But more than its talent, the film has remained a cultural touchstone since its 1995 release. Just last year, Iggy Azalea and Charli XCX paid tribute to the film in the video for their mega-hit “Fancy.” Clueless lives on because of the irrepressible charms of its actors, the witty, fast-paced dialogue, and — of course — the soundtrack.

To accompany the film, Heckerling sought out a roster of under-the-radar college rock bands and hip up-and-comers doing too-cool-for-school cover songs. (No designer impostors allowed.) The soundtrack now stands as a time capsule of ‘90s rock, and includes an impressive roster of now-famous ‘90s heavyweights, including Radiohead, who contributed an acoustic rendition of “Fake Plastic Trees,” Coolio (“Rollin with the Homies”), the Beastie Boys (“Mullet Head”), Supergrass (“Alright”), and Counting Crows (covering the Psychedelic Furs’ “The Ghost in You”). The soundtrack also fittingly features a number of female-fronted bands including Luscious Jackson (“Here”), Jill Sobule (“Supermodel”) and The Muffs, whose cover of Kim Wilde’s “Kids in America” became their best-known song.

To mark the anniversary, the soundtrack will be re-released April 7 and — in an ode to Cher Horowitz’s always-on sartorial choices — there’s a special edition pressed on yellow and black plaid vinyl available through Urban Outfitters.

As the soundtrack turns 20, TIME takes a look back with Kim Shattuck from The Muffs, Dicky Barrett from the Mighty Mighty Bosstones, Jill Sobule and Jill Cunniff from Luscious Jackson.

Kim Shattuck of The Muffs on “Kids in America”

“We were on Reprise Records at the time and they gave us one of those giant cellphones—one of those shoebox sized cellphones—and we were told not to use it unless Reprise called us, because it cost too much money to use,” says Shattuck. “So we didn’t touch it. Then one day it rang. We were totally freaked out.” It was Howie Klein, the president of their label; he wanted them to contribute a song for the Clueless soundtrack and gave them the choice between three songs. They opted for Kim Wilde’s “Kids in America,” because—as Shattuck explains—“it was the catchiest out of the three.”

Shattuck admits she’s always had a love-hate relationship with the song, since it’s undoubtedly their biggest hit—but because it was a cover, they didn’t earn as much in royalties as they would have for an original song. “We never played it live,” says Shattuck. “Never, ever, never. We’ve never even played it all the way through, except for in the studio when we recorded it.”

At one point in the Muffs’ history the band considered putting the song in rotation out of a sense of nostalgia. “Halfway through we started laughing,” says Shattuck. “The lyrics are not good. Like, they talk about East California. What is that?”

The Clueless soundtrack went gold, Shattuck notes. “But they wouldn’t give us a gold record for it.”

Dicky Barrett of The Mighty Mighty Bosstones on “Where’d You Go?”

“We were a college chart band,” says lead singer Dicky Barrett. “We didn’t have a lot of commercial success before Clueless. The song we performed in the film got some college radio play before that, but most people who recognize those songs recognize them from the movie.”

The Bosstones were actually cast in the movie, playing the band at a house party. “The reason we agreed to be in the movie was because at the time we had just found out we had poor management who had failed to pay taxes for years,” Barrett says. “We were in a tax situation and we were paid really well.”

Barrett claims that the band was actually paid better than the star, Alicia Silverstone. “There was a famous Jeopardy question, ‘Name the band that made more money than Alicia Silverstone in the movie Clueless,’” Barrett laughs. “Alex Trebek was really smarmy when he said ‘the Mighty Mighty Bosstones,’ so I believe him. We were handsomely paid—at least according to Jeopardy.”

Despite the compensation, the Bosstones were hesitant to sign on. “We knew Amy Heckerling had done Fast Times and while we didn’t have a lot of knowledge who she was, we knew that we loved that movie and felt like we were in good hands,” Barrett says. “But we were trying to do things that weren’t so commercial. We were punk rock and independent, so doing a big commercial movie was weird to us, but it was her and she had that track record.”

Heckerling seemed to determined to feature the Mighty Mighty Bosstones in the movie, even going so far as to switch up the script to make the band comfortable. “She asked if we wanted to play at a frat party, but we didn’t, so she changed it to a regular party,” Barrett says. “We hated college, and in our minds we were the antithesis of frat guys, and we didn’t want to play a frat party. We always appreciated that she was willing to make changes to the movie for us.”

“We arrived at the shoot in the morning thinking, like, ‘Oh, we have to do this for tax reasons—what are we doing?’ We showed up and we brought alcohol because we were going to shoot all day in downtown L.A. in a warehouse directly across the street from the courthouse. And in the courthouse at the time, the O.J. trial was going on,” says Barrett. “In the first take, in what was a bit of an aggressive move, I dove onto the young Hollywood extras in the crowd. Amy was directing and she loved it and so I had to spend the rest of the day stage diving at the same time for continuity. They got a little more drunk, a little more lifeless, and by the end, it looked like a wilt. I lost the will to stage dive—and that’s the take she used.”

“In hindsight, it didn’t suck,” says Barrett. “People seem to really like the movie. It was like, ‘I saw Clueless! You guys were cool and so was the movie.”

Jill Sobule on “Supermodel”

“You know that thing where you take a picture and you think, ‘Ugh, I hate it! I look awful.’ Then you look back on it and say, ‘I look really good!’ That’s how I feel about ‘Supermodel,’” says Sobule. “I recently played it with my band in New York and I got a renewed sense of pride with it and the movie.”

“The song came to me,” she explains. “I didn’t write it. They asked if I would sing it and I said I would, but only if I could add something—the eating disorder bridge.” That bridge is a cleverly subversive indictment of the beauty-industrial complex, and it’s probably the most memorable part of the song. “I was thinking about supermodels and ended up with: ‘I didn’t eat yesterday, and I’m not going to eat today, and I’m not going to eat tomorrow. I’m going to be a supermodel,’” says Sobule. “I have always tried to put a little politics or social conscience in my songs, cloaked in a silly goofiness.”

For the video, Sobule opted to do a take on another teen movie—Carrie. “I think the label ended up not liking it because I looked like Siouxsie and the Banshees or something and I burn a fashion show,” she says. “The video was so much fun.”

“My first song, ‘I Kissed A Girl’, had just come out. The label wanted to trivialize it, and I wanted it to be a subversive lesbian song, and the label fluffed it and wouldn’t let us have a kiss at the end of the video. So my thought was to have a weird-ass video for Clueless,” says Sobule. “On second thought, the movie was so good I should have had clips from the movie. It was still a good video though.”

However, Sobule didn’t get a writing credit for the bridge, even though fans seem to understand that they were her words. “If it was modern-day, I would have gotten credit, but back then I didn’t get a writer’s credit. I wasn’t as savvy as I should have been. I didn’t even think of it!” says Sobule. However she did get something out of the song: “Sometimes I’ll see something that says ‘Jill Sobule, one hit wonder’ and I’ll say, ‘Uh-uh!’ I had “Kissed A Girl” and “Supermodel.” I had two one-hits. There’s a joy in that.”

Jill Cunniff of Luscious Jackson on “Here”

“We were on Grand Royal, the Beastie Boys’ label, which went to Capitol, so it wasn’t too complicated,” says Luscious Jackson’s Jill Cunniff. “Capitol was putting out the soundtrack and they just put us on there. That’s how it was done in those days. It was just a way to get the single, ‘Here,’ out there.”

“We were always a band that was a little left of center and hard to categorize,” she says. “We didn’t have an automatic spot on the radio or an automatic place in the world, so we needed stuff like this.” Recently, Luscious Jackson has reunited and started touring; “Here” is still part of their set. “‘Here’ was a big song for us,” says Cunniff. “The movie was so big, the press around it was so big, that we got a lot of new fans from it. It really expanded our reach as a band. It was a big vehicle to push our music out and introduce us to a ton more people.”

To promote the single and the movie, Luscious Jackson appeared on MTV’s Clueless Beach Party and put out a video that featured Clueless stars Stacey Dash and Brittany Murphy intercut with clips from the movie. “We all had to learn how to roller derby for the video. It was pretty intense,” says Cunniff. “We didn’t hang out with Brittany Murphy and Stacy Dash because we spent our entire time trying to learn how to skate on a slant, which was really hard. There were a couple really close calls on that video. There was a camera arm hanging over the course and one of the roller derby-ers smacked into it and had to be taken to the hospital. Vivian [Trimble, the band’s former keyboard player] got knocked over by a roller derby lady and really messed up her neck. There were definitely some moments in that video that sounded great in the treatment, and not so much in real life.”

Cunniff’s daughters, ages 10 and 13, have now discovered Clueless, too. “My daughter’s yearbook quote is ‘As if,’,” laughed Cunniff. “It has nothing to do with me being in the movie. It’s just cool, and it makes me cool.”