“Staying Young Is Getting Old”: The Neglected Post-‘Clueless’ Career of Writer/Director Amy Heckerling

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Clueless turns 20 on July 19, and Flavorwire is celebrating all week with a series of tributes to Amy Heckerling’s era-defining teen film. Click here to follow our coverage.

When Amy Heckerling’s Clueless became an unexpected summer hit and pop culture touchstone in the summer of 1995, it was the Bronx-born writer/director’s third time capturing the zeitgeist. Her debut film, 1982’s Fast Times at Ridgemont High, became the definitive ‘80s dramatization of the teenage experience; 1989’s Look Who’s Talking was pretty much the apex of the big, dumb, high-concept gimmick comedies of the era, and was thus a monster hit too. After each of those hits came stumbles, but she always bounced back, which is why it’s so peculiar, considering its ubiquity and affection, that she’s made so few features since Clueless — only three, two of them barely released. And each tells a little story about the burdens of trying to recapture that Clueless magic.

Her first post-’95 credits were a pretty direct attempt to revisit that triumph — by writing and directing several episodes of the Clueless TV series, which premiered barely a year after the film’s bow and ran three seasons (one on ABC, two on UPN). This was nothing new for Heckerling; she turned out a quickie sequel to Look Who’s Talking that opened 14 months after the original, and she directed a few episodes of Fast Times, the belated (and short-lived) 1986 TV adaptation of her debut feature. But she didn’t make another film — aside, reportedly, from some uncredited work on A Night at the Roxbury, which she produced — for five years, until 2000’s Loser.

An amiable college-based follow-up to her high school hits, Loser stars Jason Biggs (fresh off American Pie) as a sweet kid from upstate who can’t quite fit in with his jaded classmates at NYU, but falls hard for a quirky girl (Mena Suvari, see previous comment) who is, sadly, dating their professor (Greg Kinnear, in the slimy jerk-off mode that was his default setting around this time). Heckerling wrote and directed Loser, and there’s a lot to like about it: Biggs and Suvari have a nice chemistry, the laughs are genuine, and it captures something authentic about surviving in Gotham when you’re young and broke. It was no Clueless, sure; it motors along at something closer to Fast Times’ low-key shamble than the later film’s stick-and-move.

Columbia wasn’t hoping for another Clueless, though — thanks to the over-the-title stars, they were clearly hoping for another American Pie, plopping Loser into a prime slot in July of 2000 (a year after Pie had slayed in roughly the same timeframe). But it tanked, opening in eighth place with a dire $6 million and failing to recoup its modest $20 million budget.

It took seven years to see another Heckerling movie, and its reception was even more disappointing. I Could Never Be Your Woman is an uncommonly personal film for Heckerling, who tells the story of a 40-year-old TV showrunner (well played by Michelle Pfeiffer) who finds herself romancing a much younger man (Paul Rudd, whose lovability may as well be the film’s third-billed co-star). But that’s merely the barest description of Woman, which is also, at one point or another, about body image, aging, Hollywood’s poor treatment of actresses, and even the woes of standardized testing. Oh, and Tracy Ullman pops up every once in a while as Mother Nature, to complain about baby boomers and offer up words of discouragement for our heroine.

So, as you might expect, I Could Never Be Your Woman is a bit of a mess, but if there’s one thing we shouldn’t ding a modern romantic comedy for, it’s ambition. “Don’t try to be safe,” Pfeiffer advises her daughter, and the movie follows the same advice. There’s some smart, cutting insight into gender roles (it’s kind of refreshing, how Heckerling frames Rudd the way most rom-coms treat “the girl”), and about the construct of age; everyone lies about theirs, including the full-grown stars of the high school TV show she writes for, where Pfeiffer’s attempts to remain hip and write slang-y, youthful dialogue clearly mirrors her time on the Clueless series. And (meta!) the cast of the show-within-the-movie includes Clueless movie and TV show co-star Stacey Dash (a comically impossible 40 years old at the time of the production).

Dash wasn’t the only Clueless alum Heckerling brought along as insurance; in addition to Rudd, Wallace Shawn shows up as, wouldn’t ya know it, a teacher. But in spite of all those marketable elements, the $24 million I Could Never Be Your Woman — after two years of post-production hell — never even made it to theaters, going straight to video (towards the end of an era when that route still carried only a negative connotation). Again, it’s got some problems — but it’s far better than Because I Said So, Good Luck Chuck, Music and Lyrics, and any other number of romantic comedies that were deemed good enough for theatrical release in 2007.

If Woman’s message was “Don’t try to be safe,” Heckerling’s next film (and most recent to date) did the opposite. 2012’s Vamps, as you might guess from the title, clamped on to the vampire craze, and this time, Heckerling brought along not only Shawn but Clueless star Alicia Silverstone, who’d likewise floundered in the years since Clueless. And for good measure, she had Taylor Negron reprise his Fast Times role as a pizza delivery guy.

Silverstone and Krysten Ritter play a pair of vampires doing the best they can in New York City; they refrain from human blood, feeding only on animals (a nice in-joke if you’re aware of Silverstone’s activism) and enjoying the club-heavy lifestyle necessary when you can only go out at night. The first act is mighty shaky, juggling lingo and iconography setup with sitcom-worthy groaners like “200 is the new 18” and “that took about a century off my life.”

But once she settles in and establishes the characters, Heckerling works up some clever twists on the vampire mythos, gets some big laughs (Shawn’s Van Helsing dispatches a fellow vampire by masquerading as a cable repairman, prompting this exchange: “Can Time-Warner just burst into a person’s home and kill them?” “Yes! They’re terrible!”), and mines the subplot of Silversone’s lost and rediscovered love (Richard Lewis, of all people) for some lovely and surprisingly poignant moments.

All the performers deliver — Justin Kirk is particularly effective, handily stealing every scene he slinks into — but, appropriately enough, it’s Silverstone who delivers the warmest and most memorable performance. And she also ends up playing the closest thing Vamps has to a Heckerling avatar; her undead character, who’s been around for well over a century, grouses amusingly about technology and texting and these kids today, to which Ritter responds, “Remember, we said we’d keep up with the times, even though it’s not as good as the ‘80s!”

Such concerns seem, based on her last two features, to be exhausting for Heckerling. For all her effort to give the world the Clueless follow-up it was pining for, Vamps barely performed better than I Could Never Be Your Woman; it was released to one theater for two weeks (presumably out of some sort of contractual obligation), where it grossed an anemic $3,361, and was already on DVD by the end of that 14-day run.

“Staying young is getting old,” Heckerling cracks in Vamps (via Silverstone), and it’s hard to blame her. She was over 40 when Clueless was released, yet prized for her ability to speak to their most valuable demographic. But when she couldn’t repeat it, the Hollywood mainstream was done with her — Loser was her last studio picture, her one shot to make lightening strike again, and when she didn’t, the jig was up. Never mind how many of her male contemporaries haven’t made a good movie since 1995 (Rob Reiner, Lawrence Kasdan, Tim Burton, and Robert Zemeckis leap to mind) and how many more opportunities they’ve had to do so. Apparently, when it comes to women like Heckerling (or Susan Seidelman, or Penelope Spheeris, or Allison Anders, or…) you’re only as good as your last picture — presuming, of course, that anyone actually saw it.