KENAN THOMPSON AS BARBARA BIRMINGHAM ON SATURDAY NIGHT LIVE (2007)

Reason for cross-dressing: Because Kenan became SNL's token black actor in 2003.
Complex says: OK, so this is the beginning of our Kenan Thompson portion of our list. First up to bat: Thompson as the spank-happy nanny, Barbara Birmingham. You want more Kenan? Sure you do! Keep clicking...