36. Happy Gilmore (1996)
A staple during the Adam Sandler ‘Golden Age,’ Happy Gilmore ranks as one of his very best. Possessing the driving ability of Tiger Woods and the attitude of a surly NHL enforcer, the enigmatic Gilmore breaks the typical country club vibe with his brash personality. Shooter McGavin (played by Christopher McDonald) is easily one of the most recognizable villains in all of sports comedies. The rivalry between the two is simply phenomenal.
Image Source: WingClips