TRACY MORGAN AS MAYA ANGELOU ON SATURDAY NIGHT LIVE (2002)
Reason for cross-dressing:Saturday Night Live hardly ever has black female cast members. Complex says: Random SNL fact for y'all: In the show's history, there have been only four black women in the cast (Danitra Vance, Yvonne Hudson, Ellen Cleghorne, Maya Rudolph). But it's just the darndest thing, black women keep on making news. So what does the show do to compensate? Find out the dress size for the token black guy, of course! SNL has been as flagrant as anyone over the years with its drag antics, and from 1996 until 2003, Tracy Morgan was the token black guy. In this instance, Morgan does his portrayal of poet Maya Angelou, who has been played so many times by so many black actors over the years (David Alan Grier famously pimped out Butterfinger bars as Angelou) that you’d think they get a comedian just to play her. You're next, Jay Pharoah.