Set in 1937 rural Mississippi during the Great Depression, the film's story is a modern satire loosely based on Homer's epic poem, Odyssey. The title of the film is a reference to the 1941 film Sullivan's Travels, in which the protagonist (a director) wants to film O Brother, Where Art Thou?, a fictional book about the Great Depression.
Much of the music used in the film is period folk music, including that of Virginia bluegrass singer Ralph Stanley. The movie was one of the first to extensively use digital color correction, to give the film an autumnal, sepia-tinted look. The film received positive reviews, and the soundtrack, O Brother, Where Art Thou?, using American folk music, won a Grammy Award for Album of the Year in 2001. The original band soon became popular after the film release and the country and folk musicians who were dubbed into the film, such as John Hartford, Alison Krauss, Emmylou Harris, Gillian Welch, Chris Sharp, and others, joined together to perform the music from the film in a Down from the Mountain concert tour which was filmed for TV and DVD.
Three convicts, Ulysses Everett McGill, Pete Hogwallop, and Delmar O'Donnell, escape from a chain gang and set out to retrieve a supposed treasure Everett buried before the area is flooded to make a lake. The three get a lift from a blind man driving a handcar on a railway. He tells them, among other prophecies, that they will find a fortune but not the one they seek. The trio make their way to the house of Wash, Pete's cousin. They sleep in the barn, but Wash reports them to Sheriff Cooley, who, along with his men, torches the barn. Wash's son helps them escape.
They pick up Tommy Johnson, a young black man, who claims he sold his soul to the devil in exchange for the ability to play guitar. In need of money, the four stop at a radio broadcast tower where they record a song as The Soggy Bottom Boys. That night, the trio part ways with Tommy after their car is discovered by the police. Unbeknownst to them, the recording becomes a major hit.
Near a river, the group hears singing. They see three women washing clothes and singing. The women drug them with corn whiskey and they lose consciousness. Upon waking, Delmar finds Pete's clothes lying next to him, empty except for a toad. Delmar is convinced the women were Sirens and transformed Pete into the toad. Later, one-eyed Bible salesman Big Dan Teague invites them for a picnic lunch, then mugs them and kills the toad.
Everett and Delmar arrive in Everett's home town. Everett confronts his wife Penny, who changed her last name and told his daughters he was dead. He gets into a fight with Vernon T. Waldrip, her new "suitor." They later see Pete working on a chain gang. Later that night, they sneak into Pete's holding cell and free him. As it turns out, the women had dragged Pete away and turned him in to the authorities. Under torture, Pete gave away the treasure's location to the police. Everett then confesses that there is no treasure. He made it up to convince the guys he was chained with to escape with him in order to stop his wife from getting married. Pete is enraged at Everett, because he had two weeks left on his original sentence, and must serve fifty more years for the escape.
The trio stumble upon a Ku Klux Klan rally, who are planning to hang Tommy. The trio disguise themselves as Klansmen and attempt to rescue Tommy. However, Big Dan, a Klan member, reveals their identities. Chaos ensues, and the Grand Wizard reveals himself as Homer Stokes, a candidate in the upcoming gubernatorial election. The trio rush Tommy away and cut the supports of a large burning cross, leaving it to fall on Big Dan.
Everett convinces Pete, Delmar and Tommy to help him win his wife back. They sneak into a Stokes campaign gala dinner she is attending, disguised as musicians. The group begins a performance of their radio hit. The crowd recognizes the song and goes wild. Homer recognizes them as the group who humiliated his mob. When he demands the group be arrested and reveals his white supremacist views, the crowd runs him out of town on a rail. Pappy O'Daniel, the incumbent candidate, seizes the opportunity, endorses the Soggy Bottom Boys and grants them full pardons. Penny agrees to marry Everett with the condition that he find her original ring.
The next morning, the group sets out to retrieve the ring, which is at a cabin in the valley, which Everett earlier claimed was the location of his treasure. The police, having learned of the place from Pete, arrest the group. Dismissing their claims of receiving pardons, Sheriff Cooley orders them hanged. Just as Everett prays to God, the valley is flooded and they are saved. Tommy finds the ring in a desk that floats by, and they return to town. However, when Everett presents the ring to Penny, it turns out it wasn't her ring, and she doesn't even remember where she put it.George Clooney as Ulysses Everett McGill, a man who is imprisoned for practicing law without a license. He claims to have escaped from prison so he can find a stash of money he had hidden, though in reality it is so he can get back to his family before his wife remarries. He corresponds to Odysseus (Ulysses) in the Odyssey.
John Turturro, as Pete Hogwallop, a fellow criminal who reveals little about his past. He believes in being true to one's kin, even when his cousin Washington B. Hogwallop betrays him. He dreams of moving out west and opening a fine restaurant, where he will be the maître d'. He agreed to go along with the breakout, though he only had two weeks left on his sentence.
Tim Blake Nelson as Delmar O'Donnell, a small-time crook imprisoned for robbing a Piggly Wiggly in Yazoo City; he initially claims innocence but later admits he is guilty. Delmar says he will spend his share of Everett's nonexistent money buying back his family farm, believing, "You ain't no kind of man if you ain't got land."
Chris Thomas King as Tommy Johnson, a skilled blues musician. He is the accompanying guitarist in the Soggy Bottom Boys. He claims he sold his soul to the devil in exchange for his skill on the guitar. He shares his name and story with Tommy Johnson, a blues musician with a mysterious past, who is said to have sold his soul to the devil at the Crossroads (a story more often attributed to Robert Johnson).
Frank Collison as Washington B. "Wash" Hogwallop, Pete's paternal cousin. He removes the escapees' chains but later betrays the men to the police.
John Goodman as Daniel "Big Dan" Teague, a one-eyed man who masquerades as a Bible salesman and mugs Everett and Delmar. He later reveals the identity of the trio when they are disguised at a Ku Klux Klan rally, but they kill him by cutting loose a burning cross, which falls on him and the Klansmen. He corresponds to the cyclops Polyphemus in the Odyssey.
Holly Hunter as Penny, Everett's ex-wife, who is fed up with Everett's wheeling and dealing. She divorces him while he is in prison, telling their children he was hit by a Louisville & Nashville train. She is engaged to Vernon T. Waldrip until Everett wins her back. She corresponds to Penelope in the Odyssey. (Penelope is an icon of the faithful wife, as she rejected her many suitors, stalling for time while awaiting Odysseus' return.)
Charles Durning as Menelaus "Pappy" O'Daniel, the incumbent Governor of Mississippi. He is frequently seen berating his son and his campaign managers, who are depicted as simpletons. The character is based on Texas governor W. Lee "Pappy" O'Daniel. (Flensted-Jensen elaborates on the connection between the fictional and the real Pappy O'Daniel.) He corresponds to Menelaus in the Odyssey.
Daniel von Bargen as Sheriff Cooley, a ruthless rural sheriff who, with his bloodhound, pursues the trio for the duration of the film. It is implied several times that he is the devil incarnate, and Cooley fits Tommy Johnson's description of Satan: Cooley's sunglasses evoke Satan's "big empty eyes." He eventually ambushes the escapees after they have been pardoned by the governor. He intends to hang them nonetheless, but when the valley is flooded, he, his men, and his dog all drown. He corresponds to Poseidon in the Odyssey. He has been compared to Boss Godfrey in Cool Hand Luke.
Wayne Duvall as Homer Stokes, the reform candidate in the upcoming election for Governor. He travels the countryside with a dwarf, who depicts the "little man", and a broom, with which he promises to "sweep this state clean". He is secretly an Imperial Wizard in the Ku Klux Klan. He falsely identifies Everett, Pete, and Delmar as people of color because they are dirty.
Ray McKinnon as Vernon T. Waldrip, Penny's bona fide suitor and the manager of Homer Stokes's election campaign. It has been suggested that his name is a nod to novelist Howard Waldrop, whose novella A Dozen Tough Jobs is one of the inspirations for the film. He corresponds to the Suitors of Penelope in the Odyssey.
Michael Badalucco as George Nelson, a bipolar bank robber who dislikes being called "Baby Face". The real George Nelson died in 1934, three years before the story is set. Nelson died in a shootout known as the Battle of Barrington rather than by electric chair, as suggested in the film.
Stephen Root as Mr. Lund, the blind radio station manager who records Everett's story in the song "Man of Constant Sorrow" and makes him known throughout the state. He corresponds to Homer.
Lee Weaver as the Blind Seer, a mysterious railroad man who accurately predicts the outcome of the trio's adventure as well as several other incidents. He corresponds to Tiresias in the Odyssey.
The idea of O Brother, Where Art Thou? arose spontaneously. Work on the script began long before the start of production in December 1997 and was at least half-written by May 1998. Despite the fact that Ethan described the Odyssey as "one of my favorite storyline schemes", neither of the brothers had read the epic and were only familiar with its content through adaptations and numerous references to the Odyssey in popular culture. According to the brothers, Nelson (who has a degree in classics from Brown University) was the only person on the set who had read the Odyssey.
The title of the film is a reference to the 1941 Preston Sturges film Sullivan's Travels, in which the protagonist (a director) wants to direct a film about the Great Depression called O Brother, Where Art Thou? that will be a "commentary on modern conditions, stark realism, and the problems that confront the average man". Lacking any experience in this area, the director sets out on a journey to experience the human suffering of the average man but is sabotaged by his anxious studio. The film has some similarity in tone to Sturges's film, including scenes with prison gangs and a black church choir. The prisoners at the picture show scene is also a direct homage to a nearly identical scene in Sturges's film.
Joel Coen revealed in a 2000 interview that he came to Phoenix, Arizona, to offer the lead role to Clooney. Clooney agreed to do the role immediately, without reading the script. He stated that he liked even the Coens' least successful films. Clooney did not immediately understand his character and sent the script to his uncle Jack who lived in Kentucky and asked him to read the entire script into a tape recorder. Unknown to Clooney, in his recording, Jack, a devout Baptist, omitted all instances of the words "damn" and "hell" from the Coens' script, which only became known to Clooney after the directors pointed this out to him in the middle of shooting.
This was the fourth film of the brothers in which John Turturro has starred. Other actors in O Brother, Where Art Thou? who had worked previously with the Coens include John Goodman (three films), Holly Hunter (two), Michael Badalucco and Charles Durning (one film each).
The Coens used digital color correction to give the film a sepia-tinted look. Joel stated this was because the actual set was "greener than Ireland." Cinematographer Roger Deakins stated, "Ethan and Joel favored a dry, dusty Delta look with golden sunsets. They wanted it to look like an old hand-tinted picture, with the intensity of colors dictated by the scene and natural skin tones that were all shades of the rainbow." Initially the crew tried to perform the color correction using a physical process, however after several tries with various chemical processes proved unsatisfactory, it became necessary to perform the process digitally.
This was the fifth film collaboration between the Coen Brothers and Deakins, and it was slated to be shot in Mississippi at a time of year when the foliage, grass, trees, and bushes would be a lush green. It was filmed near locations in Canton, Mississippi and Florence, South Carolina in the summer of 1999. After shooting tests, including film bipack and bleach bypass techniques, Deakins suggested digital mastering be used. Deakins subsequently spent 11 weeks fine-tuning the look, mainly targeting the greens, making them a burnt yellow and desaturating the overall image in the digital files. This made it the first feature film to be entirely color corrected by digital means, narrowly beating Nick Park's Chicken Run.
O Brother, Where Art Thou? was the first time a digital intermediate was used on the entirety of a first-run Hollywood film that otherwise had very few visual effects. The work was done in Los Angeles by Cinesite using a Spirit DataCine for scanning at 2K resolution, a Pandora MegaDef to adjust the color, and a Kodak Lightning II recorder to put out to film.
A major theme of the film is the connection between old-time music and political campaigning in the Southern U.S. It makes reference to the traditions, institutions, and campaign practices of bossism and political reform that defined Southern politics in the first half of the 20th century.
The Ku Klux Klan, at the time a political force of white populism, is depicted burning crosses and engaging in ceremonial dance. The character Menelaus "Pappy" O'Daniel, the governor of Mississippi and host of the radio show The Flour Hour, is similar in name and demeanor to W. Lee "Pappy" O'Daniel, one-time Governor of Texas and later U.S. Senator from that state. W. Lee O'Daniel was in the flour business, and used a backing band called the Light Crust Doughboys on his radio show. In one campaign, W. Lee O'Daniel carried a broom, an oft-used campaign device in the reform era, promising to sweep away patronage and corruption. His theme song had the hook, "Please pass the biscuits, Pappy", emphasizing his connection with flour.
While the film borrows from real-life politics, differences are obvious between the characters in the film and historical political figures. The O'Daniel of the movie used "You Are My Sunshine" as his theme song (which was originally recorded by real-life Governor of Louisiana James Houston "Jimmie" Davis) and Homer Stokes, as the challenger to the incumbent O'Daniel, portrays himself as the "reform candidate", using a broom as a prop.
Music in the film was originally conceived as a major component of the film, not merely as a background or a support. Producer and musician T-Bone Burnett worked with the Coens while the script was still in its working phases, and the soundtrack was recorded before filming commenced.
Much of the music used in the film is period-specific folk music, including that of Virginia bluegrass singer Ralph Stanley. The musical selection also includes religious music, including Primitive Baptist and traditional African American gospel, most notably the Fairfield Four, an a cappella quartet with a career extending back to 1921 who appear in the soundtrack and as gravediggers towards the film's end. Selected songs in the film reflect the possible spectrum of musical styles typical of the old culture of the American South: gospel, delta blues, country, swing and bluegrass.
The use of dirges and other macabre songs is a theme that often recurs in Appalachian music ("O Death", "Lonesome Valley", "Angel Band", "I Am Weary") in contrast to bright, cheerful songs ("Keep On the Sunny Side", "In the Highways") in other parts of the film.
The voices of the Soggy Bottom Boys were provided by Dan Tyminski (lead vocal on "Man of Constant Sorrow"), Nashville songwriter Harley Allen, and the Nashville Bluegrass Band's Pat Enright. The three won a CMA Award for Single of the Year and a Grammy Award for Best Country Collaboration with Vocals, both for the song "Man of Constant Sorrow". Tim Blake Nelson sang the lead vocal on "In the Jailhouse Now".
"Man of Constant Sorrow" has five variations: two are used in the film, one in the music video, and two in the soundtrack album. Two of the variations feature the verses being sung back-to-back, and the other three variations feature additional music between each verse. Though the song received little significant radio airplay, it reached #35 on the U.S. Billboard Hot Country Singles & Tracks chart in 2002. The version of "I'll Fly Away" heard in the film is performed not by Krauss and Welch (as it is on the CD and concert tour), but by the Kossoy Sisters with Erik Darling accompanying on long-neck five-string banjo, recorded in 1956 for the album Bowling Green on Tradition Records.
The film premiered at the AFI Film Festival on October 19, 2000. It grossed $71,868,327 worldwide off its $26 million budget.
Review aggregation website Rotten Tomatoes gives it a score of 77% based on 147 reviews and an average score of 7.1/10. The consensus reads: "Though not as good as Coen brothers' classics such as Blood Simple, the delightfully loopy O Brother, Where Art Thou? is still a lot of fun." The film holds an average score of 69/100 on Metacritic based on 30 reviews.
Roger Ebert gave two and a half out of four stars to the film, saying all the scenes in the film were "wonderful in their different ways, and yet I left the movie uncertain and unsatisfied".
The film was selected into the main competition of the 2000 Cannes Film Festival.
The film also received two Academy Award nominations at the 73rd Academy Awards: Best Adapted Screenplay and Best Cinematography. Cinematographer Roger Deakins was recognized with both Academy Award and ASC Outstanding Achievement Award nominations for his work on the film.
For his portrayal of Ulysses Everett McGill, George Clooney received the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy. The film was also nominated for the Golden Globe Award for Best Motion Picture – Musical or Comedy.
The Soggy Bottom Boys, the musical group that the main characters form, serve as accompaniment for the film. The name is an homage to the Foggy Mountain Boys, a bluegrass band led by Lester Flatt and Earl Scruggs. In the film, the songs credited to the band are lip-synched by the actors, except that Tim Blake Nelson does sing his own vocals on "In the Jailhouse Now." The actual musicians are Dan Tyminski (guitar and lead vocals), Harley Allen, and Pat Enright. The band's hit single is Dick Burnett's "Man of Constant Sorrow," a song that had already enjoyed much success in real life. After the film's release, the fictitious band became so popular that the country and folk musicians who were dubbed into the film, such as Ralph Stanley, John Hartford, Alison Krauss, Emmylou Harris, Gillian Welch, Chris Sharp, and others, all got together and performed the music from the film in a Down from the Mountain concert tour which was filmed for TV and DVD.