Kiss Me Stupid (1964)

Dean Martin plays a version of himself (a womanizing, heavy-drinking singer) who gets waylaid on his drive from Las Vegas to Los Angeles by a mechanic Cliff Milsap and his song writing partner Ray Walston. Instead of subjecting his wife to the singer’s lecherous ways, Walston hires local waitress Kim Novak as a stand-in while trying to sell his songs to Dino. There are some really weird sexual politics in this film. Walston is abusively jealous before Martin even comes into the picture and is willing to thoroughly upset his wife than have her around an attractive, successful man. In the end both women show how much smarter and stronger they are when compared to the men, but they endure a lot of disrespect to get there.