4. The Longest Yard - $158,119,460
The Waterboy/The Longest Yard three-four punch makes Adam Sandler the second highest-grossing sports movie star of all time, which is kind of crazy. The Longest Yard told the story of a pro quarterback, played by Sandler, who gets in trouble with the law and has to serve time. The prison warden convinces him to form a football team of convicts to play against a team of guards. With Chris Rock and Burt Reynolds by his side, this movie was meant to be a winner.