FLIP WILSON AS GERALDINE JONES ON THE FLIP WILSON SHOW (1970-1974)
Reason for cross-dressing:To please the white man Strictly for comedic purposes. Complex says: In 1970, Flip Wilson broke barriers by being the first black star to host his own variety television show. In the show’s prime, it was the second most watched program in the United States, and Flip was presented as “TV’s First Black Superstar” on a Time magazine cover in 1972. But, more importantly, well for the sake of this list at least, he was the first major black comedian to appear in drag, with his portrayal of the sassy Geraldine Jones. It quickly became one of his more popular sketches (the video above shows him with the G.O.A.T., Muhammad Ali). The show eventually got canned in '74 due to a dwindling audience but Wilson's—or better yet Geraldine's—legacy forever rest with him proudly wearing those pumps and then passing those shits down.