Major League (1989)

Long before his infamous meltdown, Charlie Sheen was a bright up-and-coming star in the 1980s and Major League is a great reminder of that. Here he's part of an ensemble cast of misfit players for the Cleveland Indians, who make it their mission to spoil the plans of the team's new owner who purposely constructed a terrible team so that she could relocate them to a new city. It's a different kind of underdog story, but one that's still fun to this day and doesn't take itself too seriously.