3. The Wedding Singer (1998)
Sandler retains some of the boisterous obnoxiousness that made Happy Gilmore work in The Wedding Singer, except this time around its tempered by a more refined script and some clever crafting from director Frank Coraci. Whereas I can see Happy Gilmores ornery foolishness grating on certain audience members, Sandlers Robbie Hart, The Wedding Singers central character, is a much less jagged pill to swallow. As the lead performer, Sandler is effortlessly likeable and most importantly, hes funny; just outrageous enough to be Sandler but restrained enough to be unabrasive. In certain scenes, he even shows keen acting prowess; when he sings his unfinished song to Drew Barrymores Julia Sullivan for example, tell me the rageful tears that fill his eyes after the final chord is struck arent as subtle and convincing as anything you might see from a more serious performer. Sandler excels when playing loveable underachievers; its a role youve seen him in many times and more but arguably, its a role he defined for himself with his turn in the Wedding Singer.