Young and popular Hollywood director John Lloyd "Sully" Sullivan (Joel McCrea) is dissatisfied with the shallow comedies that he has been making, such as "Thanks for Yesterday" and "Ants in Your Plants", despite their profitability. He lets his studio boss, Mr. LeBrand (Robert Warwick), know that he wants his next project to be a dramatic exploration of the plight of the downtrodden, based on the book "O Brother, Where Art Thou?". LeBrand wants Sullivan's next project to be another lucrative comedy, but Sullivan turns it down and, wanting to "know trouble" firsthand, begins to make plans to travel as a tramp who only has ten cents in his pocket in order to be able to direct a film that presents a genuine depiction of humanity's sorrows. His British butler Mr. Burrows (Robert Greig) and his valet (Eric Blore) both question the wisdom of Sullivan's plans. Sullivan goes ahead with his plans, dressing up like a hobo and taking to the road, where he is followed by a bus containing several staff from his movie studio, an imposition made by the studio for Sullivan's safety that no one is happy with. When Sullivan hitches a ride in a whippet tank being driven by a 13-year-old boy (Payne B. Johnson) who is learning to drive it, the bus driver steps on the gas, and the two are briefly pursued by a police motorcyclist until the whippet tank and bus turn down a side road while the police bike continues along the highway. The bumpy dirt road causes chaos on the bus. Eventually, the chase ends after the whippet tank knocks the supports off a horse-drawn hay cart, causing the horse to break free and the bus to crash into the hay. After the staff recover from the crash, some of them talk to the bus driver before one of them spots Sullivan near where the whippet tank drops him off. Sullivan persuades his guardians to leave him alone and makes an arrangement to meet with them in Las Vegas later on. Sullivan finds himself working on a nearby farm run by Miz Zeffie (Esther Howard) and Ursula (Almira Sessions). While he is chopping wood, they remark on his appearance. Later, they take him to the movies. That night, Miz Zeffie allows Sullivan to sleep in a bed where her late husband had been. After she says goodnight, Sullivan finds the door locked. He explores a little further and finds someone else in another bed on the other side of the shared bathroom. In the end, he tries to escape by knotting the bed sheets together. He makes it outside, but he rips his pants on a nail as he descends, and one of the knots comes undone, sending him straight down into a water barrel. He climbs out and flees the farm before the owners discover that he has gone. Back on the road, he hitches another ride and eventually finds himself back in a part of Los Angeles that he doesn't recognize. He goes into a nearby diner, where he meets a young actress who has struggled but failed to make it in Hollywood (Veronica Lake) and is just about to give up on her dream of stardom and return to her home. Seeing Sullivan and believing that he is a penniless tramp, she buys some breakfast for him. Sullivan repays the girl's kindness by retrieving his car from his estate and offering her a ride to wherever she wants to go, but he neglects to tell his servants about his return despite thinking that he left them a note. After they discover that the car has gone missing, they report it to the police as being stolen. As Sullivan and the girl continue their conversation, they hear the wail of a siren and see two police motorcyclists following them. Despite Sullivan's insistence that there is absolutely nothing they can do, they end up in a police lock-up. It isn't long before Sullivan's butler and valet arrive and clear things up allowing Sullivan to be released, and he persuades the officers to free the girl as well. The valet drives Sullivan and the girl back to his palatial mansion, and on the way, the tramp reveals to the girl that he is actually Sullivan the movie director. While his servants cook up some ham and eggs for breakfast, Sullivan shows the girl around his home. When she finds out about his true wealth, she gets him to show her the swimming pool, and then pushes him into it. When he asks her what the big idea is, she tells him that it is for making fun of a poor girl who had only tried to help him, by his story about being a washed-up director. After she calls him a clunk, he pulls her into the pool, and they splash around just as the servants arrive with breakfast. After the meal, the girl apologizes for pushing Sullivan in the pool, and Sullivan talks about trying his plan to live like a hobo again. The girl insists that he take her with him, but he objects to the idea, even after she threatens to throw him in the water again and Mr. Burrows agrees with the girl's suggestion of accompanying Sullivan. The girl instructs Burrows to get her some tramp clothes while Sullivan requests that he go down to the station and get him a train ticket, but when the girl refuses to tell them where she is from, Sullivan gets Burrows to grab her legs and all three of them fall into the pool. The valet comes to help Burrows out, only for Burrows to pull him in too. In the end, Sullivan agrees to the girl coming with him, on the condition that she dresses up like a boy. This time, his experiment is a success, and after they have ridden in a cattle car, eaten in some soup kitchens and slept in some homeless shelters, including one where somebody steals Sullivan's shoes, Sullivan eventually decides that he has had enough. The studio publicizes the huge success of Sullivan's experiment. The girl wants to stay with Sullivan, but he reveals to her that he is married to a wife who doesn't love him, a piece of advice that he chose to take on the pretense that he would pay less tax on a joint income, which ended up backfiring severely in many ways - his joint returns have ended up being much higher than the ones he earned when he was single, his wife (Jane Buckingham) ended up having an affair with his business manager, and she would never agree to him getting a divorce. As a gesture of thanks to the homeless people for the insights that they have given him for his next film, Sullivan decides to give them several five-dollar bills. When he reaches the train yard, somebody knocks him unconscious, steals his money and shoes and drops his body into a boxcar as it departs, but as the thief tries to escape with Sullivan's money, he is run over by another train. After the would-be thief's mangled body is found, identification cards sewn into the stolen shoes lead to the deceased thief being identified as John Sullivan. Sullivan regains consciousness in another city and with no memory about who he is or how he came to be where he is. He is discovered by a yard bull (Emory Parnell) who accosts him for trespassing in the rail yard. Still in a dazed state, Sullivan hits the yard bull with a rock, and as a result is convicted for assault and battery and sentenced to six years hard labor in a work camp. While he is working in the camp, Sullivan's memory gradually starts to come back to him. While he is there, he and the prisoners are given a special treat by being shown the Walt Disney cartoon Playful Pluto (1934), and he is surprised to find himself laughing along with the other prisoners. Sullivan is unable to either convince anybody else that he is John Sullivan or make any form of communication with the outside world, but when he sees an old newspaper with a front-page story about the unsolved mystery of "his" killing, he finds a way to solve his problems by confessing that he is the man who murdered John Sullivan. The next edition of the newspaper is printed with his face on the front page, and someone in the outside world recognizes him and makes arrangements for his release. He discovers that his wife, presuming that she is now a widow, has married his business manager, which means that if she still refuses to grant him a divorce, he will have her charged with bigamy. Back at the studio, Mr. LeBrand gives Sullivan the green light to start shooting the "O Brother, Where Art Thou?" movie, but Sullivan tells LeBrand that he has changed his mind and the next movie he wants to make now is a comedy, as a result of him seeing firsthand just how much joy such movies have brought to the downtrodden people.
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