10. Big Daddy (1999)
Not long after Happy Gilmore made him a household name, Adam Sandler offered a glimpse at his coming maturity with a movie explicitly about his unwillingness to grow up and take responsibility. In Big Daddy, Sandler’s leading loaf Sonny illegally adopts his roommate’s kid (Cole and Dylan Sprouse in their first major role) in a desperate play to win back his ex-girlfriend. But raising a child is both rewarding and far more than Sonny bargained for, his fight to maintain custody culminating in a disarmingly sweet climax at a courthouse. Poke holes at the plot all you want – it can’t stop Big Daddy from being one of Sandler’s better movies, equally crass and charming in all the best ways.
