‘Clueless’ Soundtrack: A Way Existential Look Back With Jill Sobule & Music Supervisor Karyn Rachtman

Alexander Cho | July 19, 2013 5:48 am

While we were all busy waiting for our noisy modems to connect to AOL and trying to figure out what the hell a Kato Kaelin was, an unassuming little movie about a Beverly Hills teen with a heart of gold and a fully motorized closet burst into theaters and made an indelible mark on pop culture — and pop music — history.

It was the summer of 1995  and as far as summer flicks go, Clueless stood out like a totally important red Alaïa dress: it was a smart, feel-good teen comedy that was critically well-received and a surprise box-office success. Biting, hilarious and with a rapid-fire vocabulary all its own, it had tons of heart but cleverly sidestepped the preachy schmaltz of John Hughes teen films of the ’80s. (It was the ’90s, after all, and everyone was busy learning how to be ironic.) Director Amy Heckerling struck gold in casting white-hot Alicia Silverstone as Beverly Hills teen Cher Horowitz, fresh from playing a teen psychopath in The Crush and pole-dancing with Liv Tyler in the long-format video for the Aerosmith hit “Crazy.”

Clueless’ soundtrack was peopled with big ’90s acts like Cracker, Counting Crows, Luscious Jackson and the Beastie Boys, while lesser-known groups such as Lightning Seeds, Smoking Popes and Supergrass also contributed some of the most memorable songs on the album. The mastermind behind all this was music supervisor Karyn Rachtman, who was responsible for an impressive array of definitive ’90s soundtracks (Pulp Fiction, Reality Bites, Reservoir Dogs and Boogie Nights, to name a few). We spoke with her over the phone in Los Angeles to get some choice behind-the-scenes info on the process of bringing music to Clueless. And since one of our favorite songs on the album is the Jill Sobule snark-anthem “Supermodel,” we also caught Jill Sobule on tour in New York for her reflections.

So, okay, you’re probably going, “Is this, like, an album retrospective, or what?” Let’s get started.

The Muffs — “Kids In America” in Clueless

There’s something iconic about the opening fuzzed-out power chords of The Muffs’ cover of “Kids In America” hammering away as the Paramount stars fly onto the screen in the first seconds of Clueless. Equal parts raucous, joyful and defiant, the song plays out during the film’s opening montage: Cher and her gorgeous friends from Bronson Alcott High cruising around in a brand-new Jeep with a monster sound system, posing for photo shoots with frenemies and careening down water slides in lavish Beverly Hills backyard pools.

According to Rachtman, director Heckerling’s rough cut during this montage used the original Kim Wilde version from 1981. “She put that song in the temp track and I thought it needed updating — and I suggested The Muffs,” explains Rachtman, who asked the California pop-punk band to record the cover for the film. Though The Muffs never quite hit it big, lead singer and guitarist Kim Shattuck kept active in the LA indie rock scene, and earlier this month she was tapped to replace Kim Deal on The Pixies’ 2013 European tour.

Supergrass — “Alright” in Clueless

Other montage moments in Clueless are also anchored by great songs: Cher’s photo shoot with the gang in which she tries to set up an uninterested Elton (Jeremy Sisto) with Tai (Brittany Murphy) was driven by Supergrass’ “Alright,” with its echoing, staccato refrain, “We are young! We run green! Keep our teeth nice and clean!”; elsewhere, World Party’s “All the Young Dudes” cover sails in as Cher’s voiceover laments the worthless state of high school boys and their baggy clothes — “I don’t think so!”

World Party — “All The Young Dudes” in Clueless

But it wasn’t just Cher and her friends who had music driving their scenes. Heckerling and Rachtman had the tough job of choosing “the maudlin music of the university station” to play whenever Cher’s older stepbrother Josh (Paul Rudd) appears early on in the film. Difficult to notice unless one listens closely, the film includes multiple tracks from Radiohead’s sophomore album The Bends, which was released that same year.

“Amy had thought that Radiohead was just this whiny, whiny band,” Rachtman laughs. “At the time, Radiohead wasn’t the huge band that they still are today. So, it was just a funny thing that Amy did.”

Clueless marked Rachtman’s first time working with the band, who had a reputation for being, shall we say, difficult.

“I was really scared about Radiohead,” she admits. “Because that’s one of your jobs — when you’re going to clear a song, you have to tell them the scene description. And just like with ‘Stuck in the Middle With You’ [by Stealer’s Wheel] in Reservoir Dogs—you know, he cuts his ear off—on Clueless I remember having to go to them and say the scene in the movie where she says, ‘Oh, that maudlin, whiny music…’ – I had to go them and tell them why it’s in the scene. And I was really scared to tell them.” Luckily, they said yes. An acoustic version of “Fake Plastic Trees” made it onto the album soundtrack.

One song that didn’t make it on the Clueless CD would eventually end up being the breakout single by a little-known ska band from Orange County called No Doubt. “Just a Girl” plays in the background when Cher is picking up her bestie Dionne (Stacey Dash) in the beginning of the film.

“Nobody had heard of No Doubt yet,” says Rachtman. “‘Just a Girl,’ I thought that was a great find.” However, Rachtman was stifled by record company politicking. No Doubt was signed to Interscope Records, and she was releasing the soundtrack album on Capitol Records, which wasn’t happy about her choice. “I was like, ‘This is crazy, this song’s huge!’ And they wouldn’t let me release it [as a single].”

She adds, “They wouldn’t even put it on the album.” That was way harsh, Capitol.

Coolio — “Rollin’ With My Homies” in Clueless

Tai’s memorable run-in with a clog during an out-of-control Val party resulted in another unforgettable inclusion on the soundtrack: Coolio’s “Rolling With My Homies.” Though we might forgive Tai for not exactly singing the hook correctly after her concussive party foul, the song makes for a fun through-line in the film, especially when she tries to burn the cassette single in Cher’s automatic gas fireplace. Coolio’s jam stands out as the one hip hop track on the otherwise alt-rock centric album.

The most indelible song to emerge from the Clueless soundtrack (and its main single) was Jill Sobule’s tongue-in-cheek rocker, “Supermodel.” Managing to be upbeat and catchy while also being a wry indictment of teenage girl culture and unhealthy body image standards, the song plays during a montage of Tai’s makeover at the hands of Cher and Dee. Sobule, a singer-songwriter, had scored a hit earlier that year with “I Kissed a Girl,” and was asked to sing “Supermodel,” which was written for the film by Rachtman’s frequent collaborator David Baerwald.

Jill Sobule — “Supermodel”

Sobule was initially reluctant to perform a song that was not her own. “I had never really done cover songs before,” she says. “But I kind of fell in love with it, and I thought it was great. So I said, ‘Well, OK, I’m going to add my little imprint.’”

That imprint was the song’s most memorable moment, a glibly scathing bridge about self-starvation. “[I was] thinking about supermodels — I thought, OK, so, I’ll do it, but let me put a little bridge in it, and that was: ‘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.’ I thought I would just put my little two cents in for whatever that was worth. Just so a part of it was mine. But it was a great song to begin with.”

It was, in fact, perfectly at home in a movie that jokingly warned against any activity where balls fly at one’s nose. The film’s edginess is a large part of why it we love it and the smart collection of songs that comprise its feel-good summertime soundtrack.

Rachtman, for one, had forgotten that the film was a summer smash until we reminded her: “I have a really bad memory…but I remember being at that premiere — and I was really pregnant with my son, because he was born in July. We had it outside on the big screen.”

And then, realizing out loud as if for the first time, she adds, “I’ve done a lot of really good summer soundtracks. Summer soundtracks — summer albums — are usually, like, the best, aren’t they?”

Join our Clueless soundtrack listening party today (Friday, July 19) at 4 p.m. ET. (Details here.) Jill Sobule is on tour with SNL alum Julia Sweeney this summer. Visit jillsobule.com for more information.