Being a “chick flick” and based on the 19th century Jane Austen novel “Emma,” “Clueless” (1995) isn’t usually cited when I and my friends discuss the core 1990s teen films. But 25 years after its release, the film’s (purposeful) agelessness and (inevitable) nostalgia remain effectively intertwined. It’s clear that writer-director Amy Heckerling’s film deserves a place alongside the likes of “Can’t Hardly Wait,” “Varsity Blues” and “American Pie.”
Building from Austen’s Emma Woodhouse, Heckerling and actress Alicia Silverstone – in the role she was born to play and is still most famous for – craft a teen girl who clearly comes from great literature yet fits smoothly into 1995 Beverly Hills. Cher, who we get to know intimately through voiceovers (which Silverstone excels at, paving the way for “Braceface”), is not a typical ditz. Her “Cher being Cher” qualities – such as misunderstanding that people don’t speak “Mexican,” especially if they are from El Salvador – are offset by smart observations about social status and how to attract boys.
Her blind spots are endearing, like her failure to recognize her supposed perfect boyfriend, Christian (Justin Walker), is gay, or to realize that she has been developing feelings for her ex-stepbrother Josh (Paul Rudd). (The Cher-Josh relationship is one where you really have to do the math. Knowing this comes from old literature, where incest might be more normalized, it’s crucial to note that Cher and Josh are not related. Her father, Dan Hedaya’s Mel, was Josh’s stepfather in a previous marriage. The movie doesn’t spell this out as clearly as it might have.)
“Clueless” is a cute romantic comedy, but not so formulaic that you know where it’s going, as in Heckerling’s “Loser” (2000) (for which I nonetheless have a soft spot). Nor is it the type where the comedy is broad. It rarely has laugh-out-loud jokes, preferring the smile-on-your-face variety. Cher is a self-styled matchmaker (Silverstone’s lamentably short 2003 TV series “Miss Match” sneakily follows Cher into her adult years, changing her name to Kate) and this movie includes more pairings than an entire season of a WB teen soap.
Through failed matches, we learn a lot about genuine situations. Elton (Jeremy Sisto) calculates that he and Cher are a perfect fit, since they both understand finer culture, but she’s not interested. Cher gives off vibes of interest only because she’s obsessed with pairing Elton with Tai (Brittany Murphy). Meaning well, as always, Cher sees the once-“clueless” Brookyln-accented new girl as her made-over creation who needs to be steered away from skater boy Travis (Breckin Meyer).
Cher fails to notice Elton’s interest in her and Christian’s sexual orientation not because she’s selfish, but because she has turned love into a calculation, a formula, an argument. Indeed, her school success is based on her ability to negotiate higher grades rather than to excel at the work, and her lawyer dad couldn’t be prouder. Interestingly, there’s nothing risqué about how Cher gets higher grades, as there might be in other teen movies and TV shows – many of which feature a titillating teacher-student relationship.
Cher uses her sex appeal as a tactic to attract boys, but she’s not crass or cruel as she zeroes in on targets while rejecting others. She’s a mix of innocence and street smarts (as long as she’s not driving the streets, that is) who on paper should not be likable yet is totally the heart of this movie. It’s partly Silverstone’s flawless turn, partly Heckerling’s craftsmanship.
“Clueless’ ” entire vibe is delightful as it peppers in 1990s trappings. In addition to the fashions – ranging from Cher’s carefully curated wardrobe to a montage showing boys’ baggy skater styles – the film puts Cher’s catchphrases “as if,” “not even” and “whatever” in a time capsule. That speaking style, with its emphasis on brevity, has impacted the language of today, where “nope” is used in social media to describe undesirable activities. It’s also fun to hear the language that didn’t catch on, such as “jeepin’, ” which has the oddly specific meaning of “making out in the back seat of a Jeep.” “Clueless” is a happenin’ film, but it can’t make “jeepin’ ” happen.
While nothing is safe from today’s political correctness police, “Clueless” fares decently. Cher’s “speaking Mexican” comment shows her ignorance, and she’s chastised by Josh. The teens’ description of Christian’s gayness is borderline, and “retarded” is used multiple times, but in regard to one’s own behavior. Cher’s best friend is Dionne (Stacy Dash), who is black, and Dionne’s relationship with Donald Faison’s Murray is the stable foil for every other attempted pairing.
That’s not to say the nostalgia isn’t strong with this film. When The Cranberries come on the soundtrack, and every time the late Murphy appears, you may get a lump in your throat. I wasn’t a fan of the Mighty Mighty Bosstones at the time, but when Cher and Christian dance to their live performance at the school dance, it’s vintage 1995 coolness.
I think Heckerling wanted this film to be timeless, though. The Austen style is still palpable, classic radio pop shares time with ’90s tunes, and the archetypal characters shine beyond the era’s fashion and language trappings. “Clueless” has aged into a lovable film, and one you can feel good about loving.