Up Jumped the Devil (1941)

Two ne'er-do-wells, Washington and Jefferson, just out of prison are looking for jobs so they won't get arrested for vagrancy. They find out that the wealthy Mrs. Brown is looking to hire a butler and a maid, and Jefferson talks Washington into dressing up as a woman so they can get both jobs. They get the jobs, but they soon run into Bad News Johnson, a crook they met in prison. They find out that Johnson is planning to pull a con on Mrs. Brown and he wants them to go in on it with him. Complications ensue.

Unfortunately the movie Up Jumped the Devil is not yet available on HBO Max.