directed by: Joe Swanberg, year: 2017
actors: Jake Johnson

Win It All is a character-driven crime drama from Joe Swanberg that follows a compulsive gambler who is handed a bag of cash with 24 hours to return it. As the clock ticks, he negotiates risky bets, unreliable allies, and old debts, forcing him to choose between a desperate shortcut or true redemption. The film blends dry humor with intimate, improv-heavy scenes, capturing friendship, risk, and the fragile line between luck and ruin in a modern Chicago setting.

Luck, Crime Drama, Dramedy, Indie, Character Driven