- Metropolitan (1990) — A sullen socialist falls in with a group of debutantes in "1970s" Manhattan.
- Barcelona (1994) — A naval officer crashes at his troubled cousin's Barcelona apartment in The '80s. Together they meet women and get into lots of arguments about the Cold War. This is Stillman's best-known film.
- The Last Days of Disco (1998) — A group of unlikely friends hang out at a Studio 54–type discotheque in 1980-81. The club is under investigation, and the prosecutor might be insane. The film was an obscure flop and remained so until it was released on DVD by the Criterion Collection 11 years later, renewing interest in Stillman's work and encouraging him to make...
- Damsels in Distress (2011) — Three girls try to class up their trashy university, leading them to take an interest in questionable male students. An Affectionate Parody of 1980s college comedies, though it's set in the present day.