13. William H. Macy
Macy's characters are among the biggest sympathetic sad sacks in Anderson's world of dysfunctional families and mixed-up Angelenos, which is saying a lot. In Boogie Nights, he's Little Bill, whose torment over his wife's open infidelities eventually lead to tragedy at a New Year's party. In Magnolia, he's the grown-up "Quiz Kid" Donnie Smith, a drunken has-been obsessed with a hunky bartender. Macy has made playing slightly pathetic Everymen his forte (see also: the Coen Brothers' Fargo), but he brings an added weirdness to these parts. Something wonderfully surreal is awakened in this actor whenever he works with Anderson.