Monopoly

In the hands of another director, a film based on a board game could easily become a CGI-heavy fantasy spectacle. But Tim Story’s *Monopoly* wisely grounds itself not in the world of top hats and thimbles, but in the all-too-relatable chaos of a family game night. The film transforms a living room into a comedic battleground where old rivalries and simmering tensions explode over plastic houses and paper money. It’s a quintessential Tim Story ensemble piece, centered on a family forced to confront their issues through the ruthless lens of capitalism in a box. The fast-paced, overlapping dialogue and the chemistry between the perfectly cast characters—from the hyper-competitive uncle to the slyly diplomatic grandmother—turn every roll of the dice into a masterclass of situational comedy and escalating absurdity. What truly cements *Monopoly* on this list is how it uses the game as a perfect vehicle for Story’s signature blend of heart and humor. Beneath the hilarious arguments about questionable trades and landing on Boardwalk with a hotel, the film explores themes of family legacy, ambition, and what it truly means to "win." Story excels at finding the humanity within the conflict, ensuring that even as the characters try to bankrupt each other, we never lose sight of the bonds that tie them together. It’s not a movie about property; it’s a movie about people, and the game is merely the catalyst that reveals their true natures. This focus on character-driven comedy and finding warmth in the midst of hilarious discord makes *Monopoly* a definitive Tim Story classic.