"Oscar Best Picture"

1960 · Billy Wilder · 125 min · Comedy, Drama, Romance

The Apartment is Billy Wilder's sharpest balancing act, a film that manages to be wickedly funny about corporate sleaze while also being deeply moving about loneliness and self-respect. Jack Lemmon and Shirley MacLaine give two of the finest performances of their careers, and Wilder's screenplay with I.A.L. Diamond remains one of Hollywood's best. The tonal shifts will challenge some viewers, but the film's willingness to take its characters seriously, even when the material is comic, is exactly what elevates it above standard romantic comedy.

1977 · Woody Allen · 93 min · Comedy, Romance

Annie Hall changed what a romantic comedy could be, and its influence on the genre is hard to overstate. Diane Keaton's performance remains a high point of American screen comedy, and the film's structural inventiveness still feels fresh decades later. Alvy Singer's self-absorption limits the emotional range, and some of the cultural references have faded. But as a portrait of how relationships fall apart despite the best intentions of the people in them, it still finds the nerve.