Worst: 'Benny & Joon' (1993)
Depp actually isn't that bad in this Nineties quirkfest, but his performance as Sam, a Spokane eccentric with an affinity for silent film stars, so accurately predicts his future badness that it has to be mentioned here. On the one hand, the character allows the star to display a nascent gift for physical comedy; he recreates Charlie Chaplin's dancing dinner rolls routine with such casual perfection that he makes it look easy. On the other hand, Sam is the kind of character who's clumsily assembled from a mess of eccentricities in the baseless hope that they'll cohere into a real person. He's introduced hiding in a tree for fun. That tells you everything you need to know. Perhaps no one sentence has ever articulated Depp's future better than a passing line of dialogue that's aimed at him here: "Having a Boo Radley moment, are we?"