MARTIN LAWRENCE AS SHENENEH JENKINS ON MARTIN (1992-1997)

Reason for cross-dressing: Again, for comic relief purposes.
Complex says: From the first episode to the last, Sheneneh, Martin and Gina’s nosy neighbor, was a major presence, quickly becoming a highlight on the show (for a while, at least). She would become so popular that 20 years later she would co-star in a major movie, even if that major movie is The Skank Robbers, that’s still impressive. The instant popularity of Sheneneh would lead to another popular crossing-dressing character on Martin…