2. Little Nicky
This sidesplitting 2000 comedy had Sandler playing Nicky, the slightly slow but independent son of Satan, played by Harvey Keitel. When Nicky’s brothers escape Hell, thus causing Satan to decompose, Nicky must travel up top to bring them back and save his father’s life. In his quest, Nicky makes friends with a few potheads/Ozzy Osbourne fans and falls in love with a girl, played by Patricia Arquette. Though he’s the son of Satan, moviegoers couldn’t help but root for Nicky in his quest to save the father he adores, even if he is Satan. Though an odd subject for a comedy, Sandler made it work by making Nicky a naïve yet charming guy “from the deep south” who just wants to be a good son.
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