RICKEY SMILEY AS BERNICE JENKINS IN FIRST SUNDAY (2008)

Reason for cross-dressing: Chalk it up to comic relief. Again.
Complex says: If you didn't know, Rickey Smiley is a comedian and radio personality who's best known for his prank calls. One of his more memorable characters is old lady Bernice Jenkins. She (or he?) makes a short appearance in Ice Cube's First Sunday. We're just letting you know because there is a very good chance that you didn't see this one.