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The Main Trio
Ulysses Everett McGill
Ulysses Everett McGill
Played By: George Clooney
A slick-talking, intelligent man who was sent to a penal farm, he spins a tale for the two men chained to him of a huge sack of cash from an old bank job that is in danger of being buried forever by the Tennessee Valley Authority's dam-building activities, and convinces them to escape together so they can retrieve it in time.
He's 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: He's very particular about his hair and brand of pomade, Dapper Dan. Don't offer him any other brand, and don't help yourself to his supply.
- Break the Haughty: Like his classical predecessor, Everett becomes a humbler man through his suffering.
- Con Man: He gets by on bluff and charm alone, and in fact everything we learn about him for the first two thirds of the movie is a complete lie.
- Deadpan Snarker: He has only two modes: loquacious and sarcastic. Sometimes both at the same time.
- 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: He 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 just 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. That said, true to the original character, he's a touch too arrogant about it, is quick to assume he knows more than he does, and isn't really a good leader, which sees him bouncing between this, Miles Gloriosus and Know-Nothing Know-It-All.
- Jerk with a Heart of Gold: Despite his near-constant exasperation at his two partners, Everett doesn't make fun of the plans they give him when asked what they'll do with the treasure. Everett is also a devoted father, and deeply loves Penny despite their difficulties. And despite his selfishness, when facing death he sincerely prays for his friends and family instead of thinking for himself.
- Large Ham: He's full of himself, and likes it!
- Middle Name Basis: He's almost always referred to by his middle name.
- Sesquipedalian Loquaciousness: He 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: Relatively so; he's 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
Pete Hogwallop
Played By: 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 have been turned into a toad at one point.
- Et Tu, Brute?: Gets really angry upon discovering that his cousin Wash has sold him out to the fuzz.
- I'll Kill You!: Shouts this to Wash when he realizes that Wash did indeed sell him and the others out for the bounty.Pete: I'm gonna KILL you, Judas Iscariot Hogwallop! You miserable, horse-eatin' son of a—!
- Jerk with a Heart of Gold: He's irascible and prickly, but he's fundamentally good-natured. Pete is the one who insists they have to rescue Tommy from the Klan.
- The Lancer: He is Everett's Foil, and always goes against whatever he says.
- Large Ham: In true John Turturro fashion. His ridiculous dance during Delmar's performance of "In the Jailhouse Now" must be seen to be believed.
- Thicker Than Water: He believes in this, as it's why he leads the gang to his cousin Wash's place for a place to rest, eat, and finally get the chains off. He's immediately angry when Everett proclaims Wash sold them out to the law that very night ("Wash's kin!"), and gets even moreso when Wash confirms it, so he ends up calling Wash "Judas Iscariot Hogwallop." Despite this, he calls Everett out for stealing Wash's pocket watch, as he did it before he could've known that Wash would betray them.
Delmar O'Donnell
Delmar O'Donnell
Played By: 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.
- Call to Agriculture: This is his motivation for getting the money — he wants to buy back his family farm, believing that he isn't a true man without owning land.
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The Cast Showoff: That really is Nelson singing "In the Jailhouse Now" toward the end of the movie (Every other time he sings he's dubbed by a professional singer, though). - Cloudcuckoolander: "We... thought... you... was... a toad!"
- The Ditz: Which makes him easily duped by Everett's "intelligence."
- Dumb Is Good: The dumbest of the main trio, yet also the most kind-hearted and agreeable.
- Friend to All Living Things: During lunch with Big Dan, we see Delmar covered with and enthralled by butterflies.
- Kindhearted Simpleton: He's the friendliest of the group.
- Nice Guy: He gets along well with both Everett and Pete.
Allies
Governor Pappy O'Daniel
Governor Menelaus "Pappy" O'Daniel
Played By: Charles Durning
The incumbent governor of Mississippi, who's also a flour tycoon and radioman, he's losing badly against his opponent Homer Stokes, due to being dogged by accusations of corruption, and due to the mis-management of his campaign by his two idiot helpers and idiot son. 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, and he's a politician, so of course he's one! 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 while he's griping to and 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."WE MASS-COMMUNICATIN'!"
- 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-member opponent.
- No Party Given: He is never referred to as either a Democrat or a Republican.
- Only Known by Their Nickname: "Pappy," although his real first name Menelaus is given at one point in the movie.
- Opportunistic Bastard: Going hand-in-hand with his political acumen, he wastes no time capitalizing on the popularity of the Soggy Bottom Boys when the opportunity presents itself.
- Sir Swears-a-Lot: Especially while whapping his employees with his hat.
- Surrounded by Idiots: His son and a couple of yes-men. They, uh, never debate the point.
Tommy Johnson
Tommy Johnson
Played By: Chris Thomas King
A young, but incredibly gifted blues musician whom Everett picks up on his way back from a 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: He's 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: He joins the group after being picked up by the side of the road.
- Token Minority: He's the only black one in the group of main characters.
Baby Face Nelson
George "Baby Face" Nelson
Played By: 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. He's heavily implied to have a manic-depressive disorder, his robberies being the result of a mania-fueled desire for excitement and notoriety.
- Berserk Button: Calling him "Baby Face" does cause him to lash out at the woman who does so. It also blends with Misery Trigger, but rather into a depressive episode.
- Go Out with a Smile: In the last leg of the film, the boys meet him again on his way to the electric chair. But he's in the midst of a manic episode, and he's having the time of his life laughing all the way.
- Historical Domain Character: Though the real Nelson died in 1934, whereas the film is set in 1937.
- Insistent Terminology: It's "George Nelson," not "Baby Face."
- Large Ham: In his manic moments.
- Misery Trigger: Being called "Baby Face" will send him into a depressive episode. On the other hand, it is strongly suggested that his depressive episode is a consequence of him having manic depression, and it would have hit, even if being called "Baby Face" did not bother him.
- 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: He's surprisingly genial for a bank robber, even in his low moments — until someone calls him "Baby Face."
- Trigger-Happy: To the point where he shoots some cows as he passes by them, just because he hates cows! It does end up being useful to him, as the cows wandering onto the road impede the cops giving pursuit of him, but he did it purely for self-gratification. A cow is led to his execution as a witness, implicitly a survivor, and a mobster is angry that Nelson shot his cow.
Antagonists
Sheriff Cooley
Sheriff Cooley
Played By: Daniel von Bargen
The lawman tasked with 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.
- Death by Irony: Poseidon is killed by a flood. Well, maybe just defeated. His ultimate fate is unclear.
- 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.
- Inspector Javert: A very cruel example. Getting escaped prisoners is his job, but he's outright psychotic about it (he sets a barn on fire to try to smoke them out, for crying out loud). When they get a pardon, he still captures them and gets ready to hang them (and Tommy, who has committed no crime other than accompanying them).
- Maybe Magic, Maybe Mundane: There are some hints that he might be the Devil (i.e., Tommy's description of the Devil he met at the crossroads matches him to a T), and his exposition about 'human institutions' when confronted about his methods casts more doubt on his true nature. Tommy does not recognize him when they meet, however.
- Not Enough to Bury: When the flood apparently kills him off, all that the camera shows of him is his glasses floating downstream.
- Obviously Evil: How he got the job is anybody's guess. Then again, if he really is the Devil, he probably wasn't actually chosen for it and made his own way in...
- Police Brutality: Cooley and his gang whip and torture Pete in hopes he'll own up to the whereabouts of his compatriots.
- Satanic Archetype: His cruelty and bizarre appearance, including the fact that his mirrored shades reflect flames at times, make him look like the Devil.
- 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.
Big Dan Teague
Daniel "Big Dan" Teague
Played By: 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.
He's based on Polyphemus, the Cyclops from The Odyssey, who cannibalizes Odysseus' men in violation of Sacred Hospitality.
- Arrow Catch: He 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. He's not so lucky with the giant flaming cross, though.
- Asshole Victim: He 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.
- Bait-and-Switch: At the Klan rally, it looks like he is going to be impaled through his remaining eye by a flagpole, like how Polyphemus was blinded. Big Dan catches it, but instead has a burning cross dropped on him. This is also a gag on how Polyphemus was defeated, as Odysseus used a tree trunk hardened in fire to blind the Cyclops.
- Carry a Big Stick: Big Dan at one point wields a large branch as a club, like his inspiration.
- Eyepatch of Power: He's an analogue of Polyphemus, the Cyclops in the original story. There may be a double meaning: while his rank is never stated, the chief officer of a local KKK chapter during the period was called the "Exalted Cyclops."
- Fat Bastard: He's a greedy, violent Bible salesman, played by the girthy John Goodman. Being a Klansman just solidifies it.
- Faux Affably Evil: He 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: Teague robs the heroes, eats their food, and squishes the toad Delmar thought was Pete and tried so hard to protect. And that's all before we learn he's a Klansman.
- Karmic Death: He's crushed by a flaming cross in a KKK rally.
- Large Ham: He puts up able competition for Everett himself in this area, and 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.
- Politically Incorrect Villain: As a Klansman, that's a given.
- Red Right Hand: He has one eye and is a Klansman.
- Sophisticated as Hell: As with Ulysses, he'll make a short point with long streams of eloquent dialogue.
- Stout Strength: He's capable of quite the beating with a big stick, but more impressively (given his lack of depth perception), he catches a flagstaff thrown as a javelin before it can impale him in the eye.
- Villainous Glutton: He first meets Ulysses and friends at a restaurant and eats quite a lot on their dime.
Homer Stokes
Homer Stokes
Played By: 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 will be okay with it. It's ambiguous whether or not they do, but they certainly don't appreciate him speaking ill of the Soggy Bottom Boys.
- Arson, Murder, and Jaywalking: His speech in the Klan rally has him talking about protecting their culture'n heritage from Negroes, Jews, Catholics, and those who accept the theory of evolution as true.
- Big Guy, Little Guy: With his little person sidekick, who not only plays the role of "the little man" in his political muckraking but helps him with his Klan activities, too.
- Hoist by His Own Petard: Despite loudly claiming to be a friend of the "little man" (with accompanying little person) both before and during the rally, 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.
- Honor Before Reason: In that his personal sense of honor as a Klansman requires him to jump out of his chair and demand the crowd disown the Soggy Bottom Boys for being integrated and supposedly the products of miscegenation, refusing to back down even as the crowd turns against him.
- Jerkass: He's a Klan member who wants to lynch Tommy for the crime of being black in his general area.
- Large Ham: He's not much of one normally (well, as much as a politician can be hammy), but he really cuts loose at the Klan rally. It makes sense given that he is running for governor, and a talent in public oratory would help him a lot.
- Politically Incorrect Villain: It goes without saying, given that he is a high-ranking Klansman. In addition to being a white supremacist attempting to lynch Tommy for the crime of being black in his area, he preaches to the other Klansmen about protecting their culture'n heritage and their women from Jews, Catholics, and those who believe in the theory of evolution. In his words...Homer: We aim to pull evil up by the root, before it chokes out the flower of our culture'n heritage! And our women! Let's not forget those ladies, y'all, lookin' to us for protection! From darkies! From Jews! From Papists! And from all those smart-ass folk say we come descended from the monkeys! That's not my culture'n heritage!
- Villain with Good Publicity: He's much better at campaigning than Pappy, and therefore much more popular. However, he's easily the worse of the two morally.
