Sour Grapes (1998) is a sharp comedy that explores how sudden wealth can poison even the closest friendships. Directed by Seinfeld co-creator Larry David in his feature film debut, the movie follows cousins Evan (Steven Weber) and Ritchie (Craig Bierko) whose relationship disintegrates when Ritchie wins a $20 million jackpot using two quarters borrowed from Evan. What begins as a simple dispute over gambling etiquette spirals into an increasingly absurd legal and personal battle that exposes the worst in both men.

The film benefits from Larry David's signature style of escalating social awkwardness and moral ambiguity, though it lacks the polish of his later television work. Steven Weber delivers a standout performance as the increasingly bitter Evan, while Craig Bierko captures the oblivious entitlement of the newly wealthy Ritchie. Supporting turns from Matt Keeslar, Karen Sillas, and Jennifer Leigh Warren add texture to the central conflict.

While Sour Grapes received mixed reviews upon release and holds a modest 5.8 IMDb rating, it has gained appreciation as an early showcase of Larry David's comedic sensibilities. The film's strength lies in its uncomfortable examination of greed, entitlement, and how money reveals true character. For fans of cringe comedy and character-driven humor, Sour Grapes offers an entertaining, if uneven, look at friendship tested by fortune. Watch this underrated comedy to see the seeds of the humor that would later flourish in Curb Your Enthusiasm.