MIGUEL A. NUNEZ JR. AS JUWANNA MANN IN JUWANNA MANN (2002)
Reason for cross-dressing: Jamal Jeffries, is a professional basketball player who gets kicked out of the NBA. His only hope to salvage his career is to dress like a woman, name himself Juwanna Mann, and play in the WNBA. Ugh, we feel cheap just summarizing this stupid shit. Complex says: What a terrible movie this was. How could they think this was a good idea? Even without the shitty cross-dressing element, in essence this movie is really just a woman's basketball flick. It is an untapped market for a reason, people! Sidenote: Miguel A. Nunez Jr. is probably the most convincing drag queen on this list; we honestly can't tell the difference between him and a real WNBA player.