History Characters / OBrotherWhereArtThou

* PoliticallyIncorrectVillain: It goes without saying, given that he is a high-ranking Klansman. In addition to 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. In his words

* InspectorJavert: 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), and 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).
* MaybeMagicMaybeMundane: There's some hints that he might be the Devil (i.e., Tommy's description of the Devil he met in 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.

He's based on Polyphemus the cyclops from ''The Odyssey'', who cannibalizes Odysseus' men in violation of SacredHospitality.

* BaitAndSwitch: 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.

* EyepatchOfPower: 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."
* FatBastard: He's a greedy, violent Ku Klux Klan member...

* {{Jerkass}}: Teague robs the heroes, eats their food, squishes the toad Delmar thought was Pete and tried so hard to protect. And that's all ''before'' we learn he's a member of the KKK.

* RedRightHand: He has one eye, and is a KKK member.

* StoutStrength: He's 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 before it can impale him in the eye.
* VillainousGlutton: He first meets Ulysses and friends at a restaurant, and eats quite a lot on their dime.

* PoliticallyIncorrectVillain: It goes without saying, given that he is a high-ranking Klansman. He preaches to the other Klansmen about preserving their "culture'n heritage" and their women, in his words, " 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!" And he seeks to lynch Tommy for the crime of being black in his general area.

->'''Played by:''' Creator/GeorgeClooney

->'''Played by:''' Creator/JohnTurturro

->'''Played by:''' Creator/TimBlakeNelson

[[folder:Governor Menelaus "Pappy" O'Daniel]]
->'''Played by:''' Creator/CharlesDurning

[[folder:Sheriff Cooley]]
->'''Played by:''' Creator/DanielVonBargen

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.

* AllegoricalCharacter: Much like Poseidon in ''Literature/TheOdyssey'', he represents inhuman power without mercy: in this case, the law itself. He may also actually be the Devil, so there's that.
* BigBad: 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.
* DeathByIrony: Poseidon is killed by a flood. Well, maybe just defeated. His ultimate fate is unclear.
* DirtyCop: It's clear from the get-go that Cooley doesn't care about little details like who is innocent and what their rights are.
* InspectorJavert: 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), and 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).
* MaybeMagicMaybeMundane: There's some hints that he might be the Devil (i.e., Tommy's description of the Devil he met in 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.
* NotEnoughToBury: When the flood apparently kills him off, all that the camera shows of him is his glasses floating downstream.
* ObviouslyEvil: 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...
* PoliceBrutality: Cooley and his gang whip and torture Pete in hopes he'll own up to the whereabouts of his compatriots.
* SatanicArchetype: His cruelty and bizarre appearance, including the fact that his mirrored shades reflect flames at times, make him look like the Devil.
* SinisterShades: Cooley always wears his shades, even in the dark. Disturbingly, they often reflect flames when you see a close-up of his face.

[[folder:Daniel "Big Dan" Teague]]
->'''Played by:''' Creator/JohnGoodman

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 SacredHospitality.

* ArrowCatch: 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.
* AssholeVictim: 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.
* BaitAndSwitch: 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.
* CarryABigStick: Big Dan at one point wields a large branch as a club, like his inspiration.
* EyepatchOfPower: 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."
* FatBastard: He's a greedy, violent Ku Klux Klan member...
* FauxAffablyEvil: 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, squishes the toad Delmar thought was Pete and tried so hard to protect. And that's all ''before'' we learn he's a member of the KKK.
* KarmicDeath: He's crushed by a flaming cross in a KKK rally.
* LargeHam: 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).
* TheNoseKnows: 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.
* RedRightHand: He has one eye, and is a KKK member.
* SophisticatedAsHell: As with Ulysses, he'll make a short point with long streams of [[SesquipedalianLoquaciousness eloquent dialogue]].
* StoutStrength: He's 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 before it can impale him in the eye.
* VillainousGlutton: He first meets Ulysses and friends at a restaurant, and eats quite a lot on their dime.

[[folder: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.

* DealWithTheDevil: How he learned to play the guitar.
-->'''Delmar:''' Oh, son, for that you sold your everlasting soul?\\
'''Tommy:''' Well, I wasn't usin' it.
* HistoricalDomainCharacter: He's basically an expy of the real-life blues guitarist [[https://en.wikipedia.org/wiki/Tommy_Johnson_(musician) Tommy Johnson]], as well as [[https://en.wikipedia.org/wiki/Robert_Johnson Robert Johnson]] -- both of them rumored to have gotten their musical skills in a DealWithTheDevil.
* NiceGuy: 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.
* SixthRanger: He joins the group after being picked up by the side of the road.
* TokenMinority: He's the only black one in the group of main characters.

[[folder:George "Baby Face" Nelson]]
->'''Played by:''' Michael Badalucco

[[https://en.wikipedia.org/wiki/Baby_Face_Nelson 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.

* BerserkButton: Calling him "Baby Face" does cause him to lash out at the woman who does so. It also blends with MiseryTrigger, but rather into a depressive episode.
* GoOutWithASmile: 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.
* HistoricalDomainCharacter: Though the real Nelson died in 1934, whereas the film is set in 1937.
* InsistentTerminology: It's "George Nelson," ''not'' "Baby Face."
* LargeHam: In his manic moments.
* MiseryTrigger: 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.
* MoodSwinger: 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.
* SugarAndIcePersonality: He's surprisingly genial for a bank robber, even in his low moments -- until someone calls him "Baby Face."
* TriggerHappy: 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.

->'''Played by:''' Creator/WayneDuvall

* MiseryTrigger: Being called "Baby Face" will send him into a depressive episode.

* AccidentalPublicConfession: 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 -- see HoistByHisOwnPetard.
* BigGuyLittleGuy: 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.

* LargeHam: 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.

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.

* IllKillYou: Shouts this to his cousin Wash when he realizes that Wash did indeed sell him and the others out for the bounty.

[[folder:George "Babyface" Nelson]]

* BerserkButton: Calling him "Babyface," although in an interesting variant trope it doesn't send him into a rage, but rather into a depressive episode.

* HistoricalDomainCharacter: Though the real life Nelson died in 1934, whereas the film is set in 1937.
* InsistentTerminology: It's "George Nelson," ''not'' "Babyface."

* MiseryTrigger: Being called "Babyface" will send him into a depressive episode.

* SugarAndIcePersonality: He's surprisingly genial for a bank robber, even in his low moments -- until someone calls him "Babyface."
* TriggerHappy: To the point 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.

* TriggerHappy: To the point 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.

* MaybeMagicMaybeMundane: There's some hints that he might be the Devil (i.e., Tommy's description of the Devil he met in 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 however does not recognise him though when they meet.

* BaitAndSwitch: 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 droppped 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.

* TheCastShowoff: 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).

* SophisticatedAsHell: As with Ulysses, he'll make a short point with long streams of [[SesquidepalianLoquaciousness eloquent dialogue]].

->'''Played by:''' Daniel von Bargen

* JerkWithAHeartOfGold: Despite his near-constant exasperation at his two partners, he doesn't make fun of the plans they give him when asked what they'll do with the treasure.

* JerkWithAHeartOfGold: He's irascible and prickly, but he's fundamentally good-natured.

* MaybeMagicMaybeMundane: There's some hints that he might be the Devil (i.e., Tommy's description of the Devil he met in 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.

-> '''Played by:''' Creator/GeorgeClooney

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 ''Literature/TheOdyssey'', the smart, but arrogant, hero who constantly finds himself in trouble on his journey back home to his wife.

* ConMan: He gets by on bluff and charm alone, and in fact [[spoiler: everything we learn about him for the first two thirds of the movie is a complete lie]].

-->'''Pete''': Since we been followin' your lead, we ain't got nothing but trouble.

* InsufferableGenius: 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, MilesGloriosus, and KnowNothingKnowItAll.

* SirSwearsALot: Relatively so; he's a bit loose with his "damns", but nothing that would get blanked out on basic cable.
* SophisticatedAsHell: He has, as he puts it, the "gift of gab". When he slips into InsufferableGenius mode, he'll start espousing odd facts mixed with simple, Southern colloquialisms.

-> '''Played by:''' Creator/JohnTurturro

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.

* ThickerThanWater: 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 [[EtTuBrute 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.

-> '''Played by:''' Creator/TimBlakeNelson

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.

* TheDitz: Which makes him easily duped by Everett's "intelligence".

* TheCastShowoff: 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.)

-> '''Played by:''' Creator/CharlesDurning

* OnlyKnownByTheirNickname: "Pappy", although his real first name Menelaus is given at one point in the movie.

-> '''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.

* MaybeMagicMaybeMundane: There's some hints that he might be the Devil (i.e. Tommy's description of the Devil he met in 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.

-> '''Played by:''' Creator/JohnGoodman

* EyepatchOfPower: 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".

-> '''Played by:''' Chris Thomas King

-> '''Played by:''' Michael Badalucco

[[https://en.wikipedia.org/wiki/Baby_Face_Nelson 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.

* BerserkButton: Calling him "Babyface", although in an interesting variant trope it doesn't send him into a rage, but rather into a depressive episode.

* InsistentTerminology: It's "George Nelson", ''not'' "Babyface".

* SugarAndIcePersonality: He's surprisingly genial for a bank robber, even in his low moments -- until someone calls him "Babyface".

-> '''Played by:''' Creator/WayneDuvall

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.

* CorruptHick: He runs on a platform of anti-government corruption and reform, but is actually a [[{{Jerkass}} high-ranking official]] in the Klan.

* TheCastShowOff: 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.)

!! Ulysses Everett [=McGill=] (Creator/GeorgeClooney)

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 ''Literature/TheOdyssey'', the smart, but arrogant, hero who constantly finds himself in trouble on his journey back home to his wife.

* BerserkButton: 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.
* ConMan: Everything about him for the first 2/3 of the movie is a complete lie and he gets by on bluff and charm alone.
* DeadpanSnarker: He has only two modes: loquacious and sarcastic. Sometimes both.

* IndyPloy: 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.
* InsufferableGenius: 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 kind of sees him bouncing between this, MilesGloriosus, and KnowNothingKnowItAll.

* MiddleNameBasis: Almost always referred to by his middle name.
* SesquipedalianLoquaciousness: 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'?
* SirSwearsALot: A bit loose with his "damns", but nothing that would get blanked out on basic cable.

!!Pete Hogwallop (Creator/JohnTurturro)

* ButtMonkey: He's beaten, kidnapped, and even appears to be turned into a toad.

-->'''Pete''': I'm gonna ''KILL'' you, Judas Iscariot Hogwallop! You miserable, horse-eatin' [[CurseCutShort son of a-]]!

* TheLancer: He is Everett's {{Foil}} and always goes against whatever he says.
* LargeHam: In true John Turturro fashion.
* ThickerThanWater: 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 [[EtTuBrute calling Wash "Judas Iscariot Hogwallop"]]. Despite this, he calls Everett out for stealing Wash's pocket watch.

!!Delmar O'Donnell (Creator/TimBlakeNelson)

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.

* TheDitz: Which helps him being duped by Everett's "intelligence".

* KindheartedSimpleton: The friendliest of the group.
* TheCastShowoff: That really is him singing In the Jailhouse Now toward the end of the movie.

!!Governor Menelaus "Pappy" O'Daniel (Creator/CharlesDurning)

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 helpers and idiot son. He unwittingly gives Everett and his group a variety of escapes from their troubles.

* FatSweatySouthernerInAWhiteSuit: The movie is set in the DeepSouth, so the politicians needed to be that! That said, he's more self-centered and neutral than the usual example.
* GrumpyOldMan: Until he's actually on his rival's stage, we only ever see him griping to and about his employees.

* LesserOfTwoEvils: He might be a {{Jerkass}} and very likely a CorruptPolitician, but he still comes out looking better than his KKK opponent.
* OnlyKnownByTheirNickname: "Pappy."
* SirSwearsALot: Especially while whapping his employees with a hat.
* SurroundedByIdiots: His son and a couple of yes men. They, uh, never debate the point.

!!Sheriff Cooley (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.

* AllegoricalCharacter: Much like Poseidon in ''Literature/TheOdyssey'', he represents inhuman power without mercy, in this case, the law itself. He may also actually be the Devil, so there's that.

* DeathByIrony: Poseidon is killed by a flood. Well, maybe just defeated.

* InspectorJavert: 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) and when they get a pardon, he still captures them and gets ready to hang them (and Tommy, who has done no crime at all other than being with them).
* MaybeMagicMaybeMundane: 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.

* SatanicArchetype: His cruelty and bizarre appearance, including the fact that his mirrored shades reflect flames at times, make him look like the devil.

!!Daniel "Big Dan" Teague (Creator/JohnGoodman)

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 SacredHospitality.

* ArrowCatch: 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.
* AssholeVictim: 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.
* EyepatchOfPower: He's a cyclops analogue. 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".
* FatBastard: Greedy, violent, Ku Klux Klan member...
* FauxAffablyEvil: 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. And that's all ''before'' we learn he's a member of the KKK.
* KarmicDeath: Crushed by a flaming cross in a KKK rally.
* LargeHam: Notes that it comes in handy in his line of work selling Bibles.

* SophisticatedAsHell: As with Ulysses, he can make a short point with long streams of dialogue.
* StoutStrength: 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.
* VillainousGlutton: 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.

-->'''Delmar''': Oh son, for that you sold your everlasting soul?\\
'''Tommy''': Well, I wasn't usin' it.
* HistoricalDomainCharacter: Basically an expy of the real-life blues guitarist [[https://en.wikipedia.org/wiki/Tommy_Johnson_(musician) Tommy Johnson]], as well as [[https://en.wikipedia.org/wiki/Robert_Johnson Robert Johnson]] - both of them rumored to have gotten their musical skills in a DealWithTheDevil.

* SixthRanger: Joins the group after being picked up by the side of the road.
* TokenMinority: The only black guy in the main characters.

!!George "Babyface" Nelson (Michael Badalucco)
[[https://en.wikipedia.org/wiki/Baby_Face_Nelson 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.

* BerserkButton: Calling him "Babyface".

* SugarAndIcePersonality: Is surprisingly genial for a bank robber, even in his low moments - until someone calls him "Babyface".
* TriggerHappy: To the point he shoots some cows that pass by!

!!Homer Stokes (Creator/WayneDuvall)

* AccidentalPublicConfession: 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. [[HoistByHisOwnPetard They weren't]].
* BigGuyLittleGuy: With his dwarf sidekick, who not only plays the role of "the little man" in his political muckraking, but helps him with his Klan activities, too.
* CorruptHick: Appears to be a reform candidate. And is actually a high-ranking {{Jerkass}} in the Klan.
* HoistByHisOwnPetard: 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.
* HonorBeforeReason: 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 miscegenated, refusing to back down even as the crowd turns against him.
* {{Jerkass}}: He's a Klan member who wants to lynch [[NiceGuy Tommy]] up for the crime of being black.
* LargeHam: Not so normally (well, as much as a politician can be hammy), but he really cuts loose at the Klan rally.
* VillainWithGoodPublicity: He's much better at campaigning than Pappy, and therefore much more popular. He's easily the worse of the two morally.

* TriggerHappy: To the point he shoots some [[EverythingsBetterWithCows cows]] that pass by!