Sullivan's Travels (1941)

Directed by Preston Sturges

Successful movie director John L. Sullivan, convinced he won't be able to film his ambitious masterpiece until he has suffered, dons a hobo disguise and sets off on a journey, aiming to "know trouble" first-hand. When all he finds is a train ride back to Hollywood and a beautiful blonde companion, he redoubles his efforts, managing to land himself in more trouble than he bargained for when he loses his memory and ends up a prisoner on a chain gang.

What a strange film. And instead of being a total mess, its wide swings in tone actually make the famous scene in the church hit home even harder. Still, its aspirations to social commentary are mostly limited to referencing blackface and a call to merely "make 'em laugh". Indeed, as David Trotter wrote in the LRB: "Sullivan’s Travels voices intelligent disquiet about Hollywood hustle, without being able to envisage anything better."