Cleo/Leo

Cleo/Leo (1989) is a comedy, fantasy directed by Chuck Vincent rated 4.2/10.

Chauvinistic businessman Leo Blockman picks up a woman who shoots him, causing him to fall into a river and inexplicably emerge as a woman. Renaming herself Cleo Clock, her female personality gradually begins to take over, and she's forced to navigate a sexist world while attempting to find a way to transform back into a man.