Actor: HAROLD PERRINEAUCharacter: Monica
Film: "Woman on Top"
Year: 2000
You probably don't know him by name, but you certainly can recognize his face. With "Lost" and "Oz" in his filmography, Perrineau is known for grittier roles. But it was his performance in 2000's "Woman on Top" that landed him on this list. Outshining a-then-unknown Penelope Cruz, Perrineau is hilarious as the cross-dressing Monica.
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