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Amy Heckerling Wants To Give Us A Different Singing Cher In ‘Clueless: The Musical’

It took a pessimistic girl from New York to make two of the most penetrating satires of sunny California ever committed to film. I speak of course of filmmaker Amy Heckerling, director of 1982’s “Fast Times at Ridgemont High” and 1995’s “Clueless.”

In a December 5 profile by The New York Times’ Taffy Brodesser-Akner, Heckerling reveals herself to be an indefatigable force of both self-doubt and near bottomless confidence in what may be her greatest creation: Her self-described “opposite,” Cher Horowitz.

Whereas Heckerling grew up in the outer boroughs — brunette and without much money — Cher, the protagonist of “Clueless” is the prototypical rich Valley Girl, complete with the blonde hair, ditzy and bright disposition and the Barbie dream house to go with it. About the only thing the two have in common is Judaism. Heckerling had a hand in adapting “Clueless” to a TV format in the ‘90s and just recently finished work on “Clueless: The Musical,” now in previews Off-Broadway at the Pershing Square Signature Center. With ex-Disney starlet Dove Cameron now in the role of Cher, even the Jewish connection now appears spurious.

Like the film of “Clueless” and Cher, the idea of a “Clueless” musical has a long prehistory.

“Even when we were shooting the movie,” Heckerling told Brodesser-Akner, “it felt like, at any point, it should burst out in song.”

Musicals, we learn in the profile, are among Heckerling’s favorite genre of film along with gangster movies of the Cagney era. But actually transforming the movie, itself a product of a collegiate reading of Jane Austen’s “Emma” and an episode of “The Patty Duke Show,” constitutes another reinvention for an artist whose early hits failed to translate to late career success.

After “Clueless,” Heckerling had a string of heartfelt flops like the 2000 Jason Biggs vehicle “Loser” and 2007’s “I Could Never Be a Woman” in which Michelle Pfeiffer dates a much younger Paul Rudd, which ended its development as a direct-to-video release. What caused this reversal of fortunes? Heckerling provides one hypothesis in the form of her last movie.

Heckerling’s most-recent film, 2012’s “Vamps” – another direct-to-video release – is about an immortal vampire (played by Cher originator Alicia Silverstone) struggling to stay relevant in a millennial world. Heckerling had a marrow-deep understanding of young people in the ‘80s and ‘90s. Losing that awareness may have contributed to her fading star.

But strangely, the fact that she is a woman, who worked in the film industry well before the current conversation about inclusion, doesn’t seem to factor much into Heckerling’s own reckoning of her career trajectory. She was proud to be a part of the boy’s club in her early professional life and blames herself for her lack of staying power.

“I keep thinking, like, well, it’s my fault. If I was better, it wouldn’t have happened,” Heckerling told Brodesser Akner. “I don’t go around going, boy, I’m so good, but I do see a lot of guys that I don’t think are that good and they get more chances or whatever, but I tend to think if I was better this…it wouldn’t have happened to me.”

No matter the cause, the director’s presence in the zeitgeist is now mainly in the form of loving homage.

Recent tributes to Heckerling’s “Clueless” include Iggy Azalea’s “Fancy” music video, yellow tartans on the runway, a substantial nod on the short-lived “Muppets” sitcom and even an unauthorized musical parody. But with her authorized “Clueless: The Musical,” taken away from the early producing team of Barry and Fran Weissler, who, according to the profile, wanted to make the show about class, Heckerling is in command of her own property once more. With the musical she may stage something of a comeback – or at least a return to the look-on-the bright-side outlook of her foil and avatar, Cher.

As for that announced “Clueless” remake? It can’t be helped, much as she might want it to be.

“She understands the ‘Clueless’ remake,” Brodesser-Akner wrote. “New ideas are risky.”

It seems like Heckerling learned that lesson firsthand and the hard way. Who can blame her for returning to her ’90s boom years by giving “Clueless” new life?

PJ Grisar is the Forward’s culture intern. He can be reached at [email protected].

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