VING RHAMES AS HOLIDAY HEART IN HOLIDAY HEART (2000)

Reason for cross-dressing: The main character, Holiday Heart, is a drag queen.
Complex says: This made-for-TV tear-jerker is not a comedy, nor is Ving Rhames really considered a comedian. Still, we threw him on here because he matches two criteria: He’s a black dude and he had to deal with lady Spandex putting a death grip on his crotch.