One of the great American independent films of the 1990s, the surprise hit Metropolitan, by writer-director Whit Stillman, is a sparkling comedic chronicle of a young man’s romantic misadventures while trying to fit in to New York City’s debutante society. Stillman’s deft, literate dialogue and hilariously highbrow observations earned this first film an Academy Award nomination for best original screenplay. Beneath the wit and sophistication, though, lies a tender tale of adolescent anxiety.

The Last Days of Disco (1998)

he Last Days of Disco, from director Whit Stillman, is a cleverly comic look at the early 1980s Manhattan party scene from the vantage point of the late nineties. At the center of the film’s roundelay of revelers are the icy Charlotte (Kate Beckinsale) and the demure Alice (Chloë Sevigny), by day toiling as publishing house assistants and by night looking for romance and entertainment at a Studio 54–like club. Brimming with Stillman’s trademark dry humor, The Last Days of Disco is an affectionate yet unsentimental look at the end of an era.

Barcelona (1994)

Whit Stillman followed his delightful indie breakthrough Metropolitan with another clever and garrulous comedy of manners, this one with a darker edge. A pair of preppy yet constitutionally mismatched American cousins—a salesman and a navy officer—argue about romance and politics while working in the beautiful Spanish city of the film’s title. Set during the eighties, Barcelona explores topics both heady (American exceptionalism, Cold War foreign policy) and hilarious (the ins and outs of international dating, the proper shaving method) while remaining a constantly witty delight, featuring a sharp young cast that includes Taylor Nichols, Chris Eigeman, and Mira Sorvino.