Cast of Deconstructing Harry

Caroline Aaron plays Doris, Harry's ex-wife who is frustrated with his self-destructive behavior.

Woody Allen portrays the main character, Harry Block, a successful but troubled writer who struggles with his personal relationships.

Kirstie Alley stars as Joan, Harry's former lover who has a complicated relationship with him.

Bob Balaban takes on the role of Richard, a friend of Harry who tries to help him navigate his personal issues.

Richard Benjamin plays Ken, another friend of Harry who has his own struggles to deal with.

Eric Bogosian appears as Burt, a fictional character in Harry's stories who comes to life in unexpected ways.

Billy Crystal portrays Larry / The Devil, a darkly humorous character who challenges Harry on his choices and actions.

Judy Davis stars as Lucy, Harry's girlfriend who is fed up with his erratic behavior.

Hazelle Goodman plays Cookie, a no-nonsense woman who crosses paths with Harry in a peculiar encounter.

Mariel Hemingway portrays Beth Kramer, a character in Harry's stories who reflects his inner conflicts.

Amy Irving appears as Jane, Harry's former partner who is still entangled in his messy life.

Julie Kavner plays Grace, Harry's sister whose relationship with him is strained due to his behavior.