Sullivan's Travels (1941)

The classic comedy Sullivan's Travels (1941), from writer/director Preston Sturges, follows the exploits of film director John Sullivan (Joel McCrea), a spoiled man of privilege who decides he no longer wants to make fluff. He wants to make substantive films about the plight of the poor and downtrodden, so he sets off on a journey, posing as a homeless man without a dime to his name. He soon learns that there's more to this experiment than meets the eye as life deals him bad hand after bad hand on his journey to self discovery. An interesting tidbit, the title of the Coen Brothers' film O Brother, Where Art Thou (2000) came from a throwaway joke in this film. Although the film is recognized today as a comedic masterpiece, the time in which it was made, at the height of the Hays Code, prevented any nudity from being shown. There is a supremely sexy shower scene featuring legendary screen beauty Veronica Lake, but she's more than likely wearing a bikini or some form of cover-up. Nevertheless, don't be surprised to find your hand traveling south down your pants!