Cher Horowitz is a popular, wealthy teenager in Beverly Hills who attends high school with her best friend Dionne. Cher’s beauty, sparkly-attitude, encyclopedic understanding of social circles, and knack for ‘fixing’ people and problems makes her life easy. Conversely, Cher’s ex-step-brother Josh arrives in town and, with a nerdy, drab style and tone, becomes something of a thorn in her side. Still, Josh’s presence doesn’t discourage Cher from kindling romance between her two teachers and adopting new-girl Tai has her protege. When all of Cher’s matchmaking has her longing for a boyfriend of her own, she falls for the dapper Christian—buuuut it doesn’t work out. When the now-popular Tai shows interest in Josh, Cher reacts poorly, spurring a fight between the two friends. In that moment, Cher realizes she had latent feelings for Josh and that she was ‘clueless’ in her understanding of people and priorities. She makes strides to live a more genuine, purpose-driven life, attracting Josh’s attention, and eventually drawing them together.
Clueless succeeds at both honoring and parodying ‘90s teenage culture in an endearing story of unexpected love. I initially didn’t care for the film’s shallow, consequence-free characters and gaudy style; nothing feels quite as unfair as a rich teenager. But as the story progressed, I warmed up to the film’s excess as caricature and its one-liners and catchphrases as fun nods to a moment. I dug the great ‘90s soundtrack (I’m all about the TMMB ska in act 2) and I eventually really bought into the story. This change of heart also came from how much I adored the generally good-hearted Cher (and Alicia Silverstone’s lovable performance) and the always charming, ageless Paul Rudd as Josh. I’ve never read Jane Austin’s “Emma”, from which Clueless is loosely adapted, so I didn’t see where the film was going and enjoyed the ride. I was further thrown-off by the fact that I thought—and still think—it’s kinda weird to pair Cher with her ex-step-brother. But—*whatever*.