Cleo/Leo (1989)

"A decidedly different look at the age-old relations between men and women."

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.