Cast and Crew: Amy Heckerling (Director – Fast Times at Ridgemont High, Look Who’s Talking); Brittany Murphy (Blossom), Paul Rudd, Wallace Shawn (Princess Bride)

What It’s About: High-school socialites Cher (Alicia Silverstone) and Dionne (Stacey Dash) inflict matchmaking mayhem on hapless new-girl Tai (Brittany Murphy) and their teachers (including Wallace Shawn, of Princess Bride fame).  Cher has inherited a persuasive streak from her alpha-lawyer father, Mel (Dan Hedaya), but it can’t prevent a series of backfires when she turns out to be almost as bad at matchmaking as she is at driving.  Eventually everyone — including Cher — finds love.

Why Watch it Today?: Clueless was conceived as a parody of Jane Austen’s Emma (though the well-known Gwyneth Paltrow version of that book wasn’t released until the following year), which is also about an overactive matchmaker who finds love.  Today is Jane Austen’s birthday, so if horror at Hyde Park’s mega-Colin Firth installation this summer has you shunning the more obvious choices, you can savor a classic of Nineties teen comedy.  Mention of Contempo Casuals may inspire suspicion that the nostalgia cues are actually blatant product placements (though it’s unlikely either Birkenstock or Nine Inch Nails paid to be associated with lovable stoner flake Travis).

And, just as evidence that Beverly Hills was on another planet from where the rest of us spent the ’90s: