In 1941, John L. Sullivan (Joel McCrea) is a successful, spoiled, naive director of fluffy, profitable Hollywood movies, but is determined to make a socially significant film, “O Brother, Where Art Thou.” He tells his studio boss it will be a serious exploration of the plight of the downtrodden and that he yearns to "know trouble" firsthand so he can make a such film.

He dresses as a penniless hobo and hits the road. After encountering a young failed actress (Veronica Lake), he finally succeeds in eating in soup kitchens and sleeping in homeless shelters. His experiment is publicized by the studio as a huge success. Sullivan decides to thank the homeless by handing out $5 bills, but one recipient wants more and knocks Sullivan unconscious, steals his shoes, throws him into a boxcar, then is run over by another train. He is found in Sullivan's shoes. The unrecognizable body is declared Sullivan's.

Meanwhile, Sullivan wakes up in the boxcar in another city with no memory of who he is. He picks a fight with a train yard worker, is arrested and receives a six-year sentence. In prison, he regains his memory after learning the importance of comedy when fellow prisoners enjoy a Disney cartoon.

But Sullivan cannot convince anybody of who he is. So, he confesses to his own murder. When his picture makes the front page of the newspapers, the Girl recognizes him and gets him released. He returns home with no more desire to “know trouble.”

Although this dark satire received no accolades in its time, in 1990, Sullivan's Travels was selected for preservation in the United States National Film Registry by the Library of Congress as being "culturally, historically, or aesthetically significant." In 2007, the American Film Institute ranked it as The 61st Greatest Movie of All Time. The movie's poster was ranked as #19 of "The 25 Best Movie Posters Ever" by Premiere magazine.

In 2000, Joel David Coen and Ethan Jesse Coen released a film O Brother, Where Art Thou? that borrows its title from and has many plot similarities to Sullivan's Travels. The Coen Brothers say the film is “almost what Sullivan would have ended up making” as a result of his experiences in Sullivan's Travels.

~ Rob Kerby