Cast of Play It Again, Sam

Woody Allen stars as Allan Felix, a recently divorced film critic who idealizes his hero, Humphrey Bogart, while struggling with dating and relationships.

Diane Keaton portrays Linda Christie, Allan's best friend's wife who tries to set him up on dates and has her own relationship troubles.

Tony Roberts plays Dick Christie, Allan's best friend who is initially married but later becomes single and tries to help Allan navigate the dating scene.

Jerry Lacy appears as Humphrey Bogart, the ghost of the legendary actor who appears to Allan Felix, offering him romantic advice in his time of need.

Susan Anspach plays Nancy, a woman who Allan goes on a date with but faces challenges due to his awkwardness and constant comparisons to Bogart.

Jennifer Salt takes on the role of Sharon Lake, one of Allan's dates who challenges his expectations and helps him see beyond his Bogart persona.

Joy Bang portrays Julie, another woman Allan goes out with, adding to his comedic and chaotic dating experiences in his quest for love.

Viva plays Jennifer, a character who is part of Allan's dating misadventures and provides moments of humor and reflection throughout the film.

Susanne Zenor appears as the Discotheque Girl, a brief but memorable character who crosses paths with Allan in the vibrant nightlife scene.

Diana Davila takes on the role of Museum Girl, a character who interacts with Allan at a museum, adding to the quirky encounters in his dating life.

Mari Fletcher portrays Fantasy Sharon, a dreamlike version of Sharon Lake who represents Allan's idealized romantic fantasies and aspirations.

Michael Greene appears as Hood #1, one of the characters Allan encounters in various comedic and unpredictable situations throughout the film.