The Sullivan is John L Sullivan (Joel McRae), successful Hollywood film director. As the film opens, Sullivan is trying to pitch his new picture "Brother, Where Art Thou" to two studio types. They are skeptical, because Sullivan’s stock in trade is the light romantic comedy, and the new movie is supposed to be a serious social drama.
"I want this to be a picture of dignity…a true canvas of the suffering of humanity!" One of the studio execs snorts "What do you know about suffering?" and that stops Sullivan in his tracks. He has to admit that he doesn’t know anything and that hatches an idea in his head – He’ll pose a bum, and go out in the world to see how the poor live. This will give him the credibility to make his movie.
Thus we see Sullivan the next day walking down the road in hobo gear – followed by a fully furnished motor home filled with studio personnel. Sullivan hitches a ride with a young kid in a dune buggy and tries to lose the entourage. This sequence is a marvel of slapstick comedy as the motor home tries to keep up to the speeding dune buggy, and is reduced to a shambles in the process.
This fiasco just strengthens Sullivan’s resolve and he is able to convince the studio that they don’t have to have him followed. So off he goes again. We next see him chopping wood for a couple of women, and it soon becomes clear that the women don’t want him exclusively for chores, going so far as to lock him in his room. He makes his escape with that oldest of movie clichés – The rope made of bedding.
A breakfast stop at a roadside diner leads to a meeting with a down-on-her-luck wannabe actress (Veronica Lake), and the two strike up a friendship over coffee. What’s marvelous in this scene is the way that Sullivan keeps his secret from the girl, despite the fact that he really, really wants to tell her who he is.
"Give me a letter of introduction to Lubitsch."
"I might be able to do that – Who’s Lubitsch?"
The girl decides to go along with Sullivan on his travels (She knows the truth by now), and he starts making plans to jump a freight train. There’s a terrific moment when Sullivan’s butler calls the railroad office. "If a hobo were going to jump on the 5:48 train, where should he do it from?"
With Sullivan and the girl hopping trains and travelling around the country, Sturges takes a step back and lets us experience the journey as they do. We see hobos everywhere, sleeping outdoors and grabbing meals where they can. The Depression was still fresh in everyone’s minds in 1941, and we are quietly reminded of the devastation it caused.
This trip gives Sullivan the experience that he thinks he needs, but he makes the fateful decision to go out one last evening and distribute money to the tramps. The result is that he is beaten, robbed, and thrown unconscious onto a freight train. To top it all off, a violent altercation with a railway worker gets him thrown in jail.
Sullivan’s stint in jail leads to the scene that is the centerpiece of the film, when the convicts go to a "picture show" at a black church. They march in slowly, in chains, to the sounds of the congregation singing. The lights go down, and the audience is treated to a Disney cartoon of Pluto fighting a losing battle with a sheet of flypaper. The convicts roar with laughter and eventually so does the movie director who was tired of making comedies.
John L. Sullivan the director comes to realize that there isn’t anything wrong with giving people something to laugh at. Preston Sturges the director has it both ways. His films are textbook slapstick comedies, with pies in the face and people falling into rainbarrels, but he also dished out a little medicine with the sugar.