Every Adam Sandler Movie Ranked Worst To Best

7. Big Daddy (1999)

Big Daddy has Sandler in his most comfortable role, cast as a 20-something slacker who's forced to confront his life's trajectory. This time, the actor is burdened with caring for the estranged child of his successful roommate.

With great work from co-stars Dylan and Cole Sprouse, Jon Stewart and Joey Lauren Adams, Big Daddy is outrageous and crass, allowing Sandler to lean into his wilder antics whilst in the presence of a child who follows his every move, but it's also a clear-eyed reminder of how sensitive an actor he really is at heart.

Of all his late-in-life coming-of-age comedies, Big Daddy may just be the best display of the Sandman's tastes and talents.