The four men drive up to a radio station with call letters WEZY. Inside, they pose as a group named the Soggy Bottom Boys and in exchange for a few dollars, record a bluegrass song called "Man of Constant Sorrow," which quickly becomes a big hit. Leaving the station, they encounter Mississippi Governor Menelaus "Pappy" O'Daniel, who presumably resides in the town of Sparta (if we recall our Homer correctly). The Governor will eventually play a key role in helping the escapees in return for their support in his bid for reelection.
Tommy soon leaves the group, and the next day the three escapees are driving along when they see three beautiful women washing clothes at a river. As in Homer's Sirens episode, the three women behave seductively toward the men. Everett, Pete, and Delmar are mesmerized as the women sing the old folk lullaby "Didn't Leave Nobody but the Baby." After the three men drink some whiskey from a jug, they fall asleep, and when Everett and Delmar awake, Pete is missing.
Everett and Delmar go into the next town, where they run into a one-eyed giant of a man named Big Dan Teague (John Goodman), a Bible salesman. Big Dan goes on a rampage, knocks out both Everett and Delmar, and steals their money and their car. This incident, of course, parallels the Cyclops episode in The Odyssey.
Everett and Delmar eventually recover consciousness and hitch a ride into Ithaca. Everett encounters three of his daughters, who say that Penny (Holly Hunter) is getting married tomorrow. Everett tells his daughters, "I am the only daddy you got. I am the damn paterfamilias." But one of his daughters immediately reminds Everett of the uphill struggle he's going to have in winning Penny back, "But you ain't bona fide!"
Everett goes into the local Woolworth, where he finds Penny shopping. Everett expresses his irritation at Penny for telling his daughters that he had been hit by a train, "It does put me in a damned awkward position vis-a-vis my progeny." Penny tells him she is marrying Vernon Waldrip tomorrow, and Everett angrily exclaims, "Why, you lyin' unconstant succubus!" The Woolworth manager doesn't get the possessive form of the name of the five-and-dime quite right as he ejects Everett, telling him, "And stay out of the Wool's Worth!"
At this point, it doesn't look like Everett has much chance with Penny, and he and Delmar are still fugitives from the law. Also, we learn that Pete has been captured and is back on the chain gang. But the movie still has several surprises in store as Everett, Pete, and Delmar eventually get entangled with the Ku Klux Klan, perform as the Soggy Bottom Boys at a gubernatorial campaign rally, and get swept up in a huge flood created by the Tennessee Valley Authority.
The Coen brothers are obviously steeped in film history, and O Brother alludes to at least 20 other movies, including The Birth of a Nation, I Am a Fugitive from a Chain Gang, It Happened One Night, and more than one of the Marx Brothers films. The title of the Coen brothers' movie is drawn from the classic 1941 Preston Sturges comedy Sullivan's Travels. The Sturges film is about a fictional Hollywood director who intends to make a movie that will be called O Brother, Where Art Thou?, and the Coen brothers' little joke is that they have actually made that film some 60 years later.
George Clooney's portrayal of Ulysses Everett McGill in O Brother is outstanding, and his performance in the role is appropriately reminiscent of Clark Gable. The Coens came up with a great Dust Bowl-like look for the film, as explained in the "Painting with Pixels" special feature on the DVD. But in the end, it's songs like "Keep on the Sunny Side," "I'll Fly Away," "In the Jailhouse Now," and "Hard Time Killing Floor Blues" that give the movie its resonance. I found O Brother, Where Art Thou? to be very entertaining, and I recommend it highly.