#5 Major League (1989) | Stream for $3 / Own for $10 @ Amazon.com
Cleveland is the charter city of underdogs. So when the scheming owner of the Cleveland baseball Indians purposefully fills the roster with has-beens, criminals, and no-talents so that she can justify moving the team to Miami, the Indians become the favorite underdogs in a city of underdogs.
But misfits like Rick “Wild Thing” Vaughn (Charlie Sheen), Pedro Ceranno, and Willie “Mays” Hayes (Wesley Snipes ruin her plan by beating the Yankees to win the division. That remains the proudest sports moment Cleveland has enjoyed in the past several decades.