It’s been over two decades since Everett McGill tried to find his "treasure" and some decent hair pomade. Honestly, looking back at the year 2000, nobody expected a Depression-era retelling of Homer’s Odyssey—set in the deep South and fueled by bluegrass—to become a cultural juggernaut. It sounds like a disaster on paper. A bunch of chain-gang escapees wandering through Mississippi, meeting bank robbers and sirens? But O Brother, Where Art Thou? didn't just work. It changed how we think about movie soundtracks and period pieces forever.
The Coen Brothers were coming off The Big Lebowski, which wasn't even a hit yet. They had this weird idea. They wanted to make a movie where the music wasn't just background noise, but the actual heartbeat of the story. They hired T Bone Burnett before they even finished the script. That’s backwards. Usually, the composer gets the scraps at the end. Not here.
The Myth of the "Soggy Bottom Boys"
People still ask if the Soggy Bottom Boys were a real band. They weren't. Not really. While George Clooney looked the part of the dapper, fast-talking Ulysses Everett McGill, he didn't actually sing "Man of Constant Sorrow." That was Dan Tyminski, a powerhouse from Alison Krauss’s band, Union Station. Clooney reportedly spent weeks practicing, but when he stepped up to the mic, the Coens realized his voice just didn't have that "high lonesome" bluegrass grit.
Tyminski’s voice is what you hear. It’s haunting. It’s raw.
The song itself wasn't new, either. "Man of Constant Sorrow" was first published by Emry Arthur in 1928. It’s a folk staple. But the movie’s version turned a dusty record into a platinum-selling single. The soundtrack for O Brother, Where Art Thou? eventually went eight times platinum. It won the Grammy for Album of the Year in 2002, beating out OutKast and U2. Think about that for a second. A collection of old-timey spirituals and Appalachian folk music dominated the pop charts in the era of Britney Spears and TRL.
It was a total fluke that felt like destiny.
Why the Homeric Parallels Actually Matter
If you haven't read The Odyssey since high school, you might miss just how deep the Coens went with the references. Or how much they poked fun at them. Everett is Odysseus. Delmar and Pete are his loyal, if slightly dim-witted, crew. You’ve got the Cyclops in the form of Big Dan Teague, the one-eyed Bible salesman played by John Goodman.
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Then there are the Sirens.
The scene at the river is mesmerizing. It’s shot with this hazy, golden glow. The washing of the clothes, the singing of "Didn't Leave Nobody but the Baby"—it captures that specific Coen Brothers magic where things feel dreamlike but dangerous. When Delmar thinks Pete has been turned into a "toad," it’s a direct nod to Circe turning Odysseus’s men into swine. It’s absurd. It’s hilarious. And yet, the movie plays it with a completely straight face.
Roger Ebert once noted that the Coens often treat their characters like puppets, but in O Brother, Where Art Thou?, there's a genuine affection for these losers. They’re searching for something. Even if Everett’s "treasure" is just a lie to get his friends to help him win back his wife, Penny (the movie's Penelope), you still want him to succeed.
That Digital Sepia Look
Have you ever noticed how the movie looks like an old postcard? That wasn't just a lens filter. This was actually the first feature film to use a digital master for color grading.
Cinematographer Roger Deakins was frustrated. He wanted the film to look like an old hand-tinted photograph, but Mississippi in the summer is aggressively green. Everything is lush. He couldn't get the "dry, dusty" look he wanted through traditional chemistry. So, they scanned the entire film into a computer—a massive undertaking at the time—and digitally tweaked every single frame to desaturate the greens and boost the oranges and yellows.
It changed the industry.
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Before this, digital intermediate (DI) was for visual effects shots only. After Deakins did it, every Hollywood director wanted that level of control. If you love the stylized looks of modern cinema, you can thank Everett McGill’s quest for Dapper Dan pomade for proving it was possible.
The Music as a Character
We have to talk about the "Midnight" scene. When the boys stumble upon the KKK rally, it’s one of the most chilling and visually striking sequences in modern film. The choreography of the marchers is terrifyingly precise. And then you hear Ralph Stanley.
The late Ralph Stanley sang "O Death" for that sequence. He was a legend of the genre, but this movie introduced him to a whole new generation. He reportedly told T Bone Burnett that he wanted to sing it a cappella to make it more eerie. He was right. That one song won a Grammy for Best Male Country Vocal Performance. Stanley was 75 at the time.
The film also highlighted the contributions of Black artists to the Southern musical tradition. The opening scene with the chain gang singing "Po' Lazarus" uses a real 1959 recording from a Mississippi state penitentiary. James Carter, the man leading the song in that recording, was tracked down decades later by Burnett. He was a retired ship worker in Chicago who didn't even know he was on a hit soundtrack. They gave him a platinum record and his royalty checks.
It’s these layers of history that give the movie its weight.
Common Misconceptions About the Film
Some people think the Coens are experts on Greek mythology. They aren't. In fact, they famously admitted they never actually read The Odyssey. They just knew the "greatest hits" of the story through pop culture and movies like Jason and the Argonauts.
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Another thing? The timeline is a bit of a "folk-tale" version of the 1930s. Pappy O'Daniel was a real person—Wilbert Lee "Pappy" O'Daniel was the governor of Texas, not Mississippi—but he was every bit the flamboyant showman depicted by Charles Durning. The movie blends real history, like the legend of bluesman Robert Johnson (played by Chris Thomas King), with pure fiction. It doesn't care about being a documentary. It cares about being a tall tale.
Why We Still Watch It
Life is messy. We’re all "men of constant sorrow" in one way or another, looking for a way home.
The humor holds up because it’s character-driven. Delmar (Tim Blake Nelson) is the heart of the group. His "we're gonna be millionaires" optimism is infectious. Pete (John Turturro) is the high-strung realist who just wants to get his farm back. They’re a perfect trio.
If you want to experience the film’s legacy today, don't just rewatch it. Dive into the "Down from the Mountain" concert film. It features the actual artists from the soundtrack performing at the Ryman Auditorium. It captures the soul of the project in a way a studio recording can't.
Actionable Ways to Explore the Film’s Legacy
- Listen to the "Harry Smith Anthology of American Folk Music." This was the primary inspiration for T Bone Burnett’s curation of the film’s sound. It’s the "Old, Weird America" that the Coens were trying to capture.
- Watch "Sullivan's Travels" (1941). The title O Brother, Where Art Thou? is actually a reference to this Preston Sturges film. In that movie, the protagonist wants to make a serious social drama called—you guessed it—O Brother, Where Art Thou?. The Coens basically made the movie he couldn't.
- Trace the Digital Color Grading. Watch a movie from 1998 and then watch this one. Notice the difference in the color palette. This was the "Patient Zero" for the digital look of 21st-century movies.
- Visit the Delta Blues Museum. If you're ever in Clarksdale, Mississippi, go there. It contextualizes the Tommy Johnson character and the "crossroads" myth that the film uses so effectively.
O Brother, Where Art Thou? remains a masterpiece because it refuses to be just one thing. It’s a comedy, a musical, a Greek epic, and a historical fantasy. Most importantly, it reminds us that even when you’re "bona fide" and in a tight spot, there’s usually a song that can get you through it. Just make sure you have enough pomade. Or a hairnet.
Whatever works.