Ulysses Everett McGill (George Clooney)
A slick-talking, intelligent man who was sent to the penal farm for practicing law without a license. He gets word that his wife is soon re-marrying, but can only make it in time to stop the wedding if he convinces the two men chained to him to agree to help him escape. Accordingly, he spins a story of a huge sack of cash from an old bank job that is in danger of being buried forever if they don't reach it in time.
Based on Odysseus from The Odyssey, the smart, but arrogant, hero who constantly finds himself in trouble on his journey back home to his wife.
- Berserk Button: Is very sensitive about his hair and brand of pomade, Dapper Dan. Don't offer him any other brand and don't help yourself to his supply.
- Con Man: Everything about him for the first 2/3 of the movie is a complete lie and he gets by on bluff and charm alone.
- Deadpan Snarker: He has only two modes: loquacious and sarcastic. Sometimes both.
- Guile Hero: Much like the character he's based on. Subverted, however; he makes his way in life by being charismatic and eloquent, but he's actually not that good at it, largely due to his overconfidence and vanity.
- First Father Wins: His wife is getting ready to marry again, but eventually goes back to him (with all their children). Maybe. If he can find that ring...
- The Hero: Or so he thinks.Pete: Since we been followin' your lead, we ain't got nothing but trouble.
- Indy Ploy: Clearly makes things up on the fly, with maybe an hour's preparation. They're successful for about as long, and Pete's quick to complain that they jump from one batch of trouble to the next.
- Insufferable Genius: Relatively. He's got a quick mind at least and is quick to try and prove it, which is magnified when he's standing next to Pete and Delmar.
- Large Ham: He's full of himself, and likes it!
- Sesquipedalian Loquaciousness: Likes to put on an air of sophistication and intelligence by using big fancy words to explain things in a verbose manner.Everett: Say, any of you boys smithies? Or, if not smithies per se, were you otherwise trained in the metallurgic arts before straitened circumstances forced you into a life of aimless wanderin'?
- Sir Swears-a-Lot: A bit loose with his "damns", but nothing that would get blanked out on basic cable.
- Sophisticated as Hell: He has, as he puts it, the "gift of gab". When he slips into Insufferable Genius mode, he'll start espousing odd facts mixed with simple, Southern colloquialisms.
- Surrounded by Idiots: A common complaint of his. ("You two are just dumber than a bag of hammers!")
Pete Hogwallop (John Turturro)
In jail for unknown reasons, Pete only had two weeks left on his sentence, but Everett's treasure is too tempting to pass up. Extremely rough-around-the-edges, but honest to a fault, Pete constantly butts heads with Everett, but continues to tag along in the hopes of using his share of Everett's treasure to open up his own restaurant.
- Butt-Monkey: He's beaten, kidnapped, and even appears to be turned into a toad.
- Jerk with a Heart of Gold: He's irascible and prickly, but he's fundamentally good-natured.
- The Lancer: He is Everett's Foil and always goes against whatever he says.
- Large Ham: In true John Turturro fashion.
Delmar O'Donnell (Tim Blake Nelson)
A dim-witted but kindhearted man in prison for robbing a convenience store in Yazoo. He's superstitious and gullible, but ultimately the most decent of the bunch. He's far more agreeable than Pete, and dreams of buying back his family farm from the bank that foreclosed on it with his share of the treasure.
- Cloudcuckoolander: "We... thought... you... was... a toad!"
- The Ditz: Which helps him being duped by Everett's "intelligence".
- Dumb Is Good: The friendliest of the group.
- Nice Guy: He gets along well with both Everett and Pete.
Governor Menelaus "Pappy" O'Daniel (Charles Durning)
The incumbent governor of Mississippi, also a flour tycoon and radioman. He's losing badly against his opponent Homer Stokes, due both to being dogged by accusations of corruption, and due to the mis-management of his campaign by his two idiot sons. He unwittingly gives Everett and his group a variety of escapes from their troubles.
He's a Composite Character representing both Menelaus and Zeus from The Odyssey, being a helpful authority figure in contrast to Sheriff Cooley.
- Fat, Sweaty Southerner in a White Suit: The movie is set in the Deep South, so the politicians needed to be that! That said, he's more self-centered and neutral than the usual example.
- Grumpy Old Man: Until he's actually on his rival's stage, we only ever see him griping about his employees.
- Historical In-Joke: Pappy O'Daniel was a Texas senator, but here he's the Mississippi governor.
- Large Ham: In both size and boisterous attitude.
- Lesser of Two Evils: He might be a Jerkass and very likely a Corrupt Politician, but he still comes out looking better than his KKK opponent.
- Only Known by Their Nickname: "Pappy."
- Sir Swears-a-Lot: Especially while whapping his employees with a hat.
- Surrounded by Idiots: His son and a couple of yes men. They, uh, never debate the point.
Sheriff Cooley (Daniel von Bargen)
The lawman responsible for bringing Everett's group back to the farm. He's a heartless man who takes a perverse pleasure in pursuing the boys, and clearly plans to summarily execute them rather than bring them in. He's implied at various points to be the Devil himself, aiming to collect on a debt he's owed.
He represents Poseidon from The Odyssey being a completely antagonistic authority figure who is constantly in the way of Everett's journey home.
- Allegorical Character: Much like Poseidon in The Odyssey, he represents inhuman power without mercy, in this case, the law itself. He may also actually be the Devil, so there's that.
- Big Bad: Of all the colourful characters the escapees meet on their journey, Cooley is definitely the most dangerous and dogged in his pursuit to capture and kill the three.
- Dirty Cop: It's clear from the get-go that Cooley doesn't care about little details like who is innocent and what their rights are.
- Maybe Magic, Maybe Mundane: There's some hints that he might be the Devil (ie. Tommy's description of the Devil he met in the crossroads), and his exposition about 'human institutions' when confronted about his methods casts more doubt to his true nature.
- Obviously Evil: How he got the job is anybody's guess.
- Police Brutality: Cooley and his gang whip and torture Pete in hopes he'll own up to the whereabouts of his compatriots.
- Sinister Shades: Cooley always wears his shades, even in the dark. Disturbingly, they often reflect flames when you see a close-up of his face.
Daniel "Big Dan" Teague (John Goodman)
A greedy, sadistic, one-eyed Bible salesman, taking advantage of the Depression to push his product. He first encounters Everett's group at a restaurant where he tricks them into paying for his meal and then violently mugs them. He later appears at a Ku Klux Klan rally, revealing the full extent of his cruelty.
Based on Polyphemus the Cyclops from The Odyssey, who cannibalizes Odysseus' men in violation of Sacred Hospitality.
- Arrow Catch: Catches the Confederate flag hurled like a javelin between his hands before it can stab him in the face, which gets a few impressed cheers from his fellow klansmen. Not so lucky with the giant flaming cross though.
- Asshole Victim: Mugs the heroes after they pay for his meal, and then is later present at a Klan rally. Once a giant, flaming cross falls on top of him, we're given exactly nothing to mourn.
- Eyepatch of Power: He's a cyclops analogue.
- Fat Bastard: Greedy, violent, Ku Klux Klan member...
- Faux Affably Evil: Puts up a friendly, amicable front before showing his true colors by beating the hell out of Everett and Delmar and robbing them blind.
- Jerkass: Robs the heroes, eats their food, and squishes the toad they thought was Pete, and Delmar tried so hard to protect. Oh, and he's a member of the KKK.
- Karmic Death: Crushed by a flaming cross in a KKK rally.
- Large Ham: Notes that it comes in handy in his line of work selling Bibles.
- The Nose Knows: He noticeably takes off his hood and gets a big sniff of the air before he rushes after the heroes and reveals them, all but stating he recognized Ulysses' Dapper Dan.
- Red Right Hand: He has one eye, an is a KKK member.
- Sophisticated as Hell: As with Ulysses, he can make a short point with long streams of dialogue.
- Stout Strength: Capable of quite the beating with a big stick, but more impressively (given his lack of depth perception) catches a flag staff thrown as a javelin.
- Villainous Glutton: Meets Ulysses and friends at a restaurant, and eats a lot.
Tommy Johnson (Chris Thomas King)
A young, but incredibly gifted blues musician whom Everett picks up on his way back from the crossroads from selling his soul to the Devil for his musical talent. Despite his obvious talent, he lives in constant fear of the Devil coming to collect.
- Deal with the Devil: How he learned to play the guitar.Delmar: Oh son, for that you sold your everlasting soul?
Tommy: Well, I wasn't usin' it.
- Historical Domain Character: Basically an expy of the real-life blues guitarist Tommy Johnson, as well as Robert Johnson - both of them rumored to have gotten their musical skills in a Deal with the Devil.
- Nice Guy: It's kind of ironic, seeing as how he sold his soul to the Devil, but Tommy is one of the nicest guys in the film.
- Sixth Ranger: Joins the group after being picked up by the side of the road.
- Token Minority: The only black guy in the main characters.
George "Babyface" Nelson (Michael Badalucco)The famous bank robber himself, Nelson runs into the boys by chance and takes them along on one of his bank jobs. He falls into a funk immediately after, wandering off and allowing the boys to enjoy the spoils on their own. Heavily implied to be manic-depressive, his robberies being the result of a mania-fueled desire for excitement and notoriety.
- Berserk Button: Calling him "Babyface".
- Historical Domain Character: Though the real life Nelson died in 1934, whereas the film is set in 1937.
- Large Ham: In his manic moments.
- Mood-Swinger: We see him cycle through highs of gleeful violence and throwing money around, along with lows of sitting and moping. Ulysses suggests he's what we'd call bipolar nowadays.
- Sugar-and-Ice Personality: Is surprisingly genial for a bank robber, even in his low moments - until someone calls him "Babyface".
- Trigger Happy: To the point he shoots some cows that pass by!
Homer Stokes (Wayne Duvall)Pappy O'Daniel's electoral opponent, Stokes is running as a reform candidate in a brilliant and highly successful campaign using a dwarf to represent his friendship with "the little man." Despite his posturing as a muckraking populist, Stokes is actually a deeply malicious man and a high-ranking member of the local Ku Klux Klan. His campaign manager, Vernon T. Waldrip, is soon to marry Everett's wife.
- Accidental Public Confession: He has to admit that he was at a Klan rally in order to out the heroes as escaped convicts. He doesn't seem to mind though, thinking his constituents would be okay with it. They weren't
- Corrupt Hick: Appears to be a reform candidate. And is actually a high-ranking Jerkass in the Klan.
- Hoist by His Own Petard: Despite loudly claiming to be a friend of the "little man" (with accompanying little person) both before and during, he can't read the mood of the crowd when he interrupts the Soggy Bottom Boys' performance at his own campaign rally and is consequently run out of town on a rail.
- Jerkass: He's a Klan member who wants to lynch Tommy up for the crime of being black.
- Large Ham: Not so normally (well, as much as a politician can be hammy), but he really cuts loose at the Klan rally.
- Villain with Good Publicity: He's much better at campaigning than Pappy, and therefore much more popular. He's easily the worse of the two morally.