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  • After rewatching O Brother, Where Art Thou?, I realized the irony of the governor being named after Menelaus, Helen's husband from The Iliad. The Menelaus of lore started the Trojan War, the reason why Odysseus left home in the first place, but the Menelaus of the film pardons our heroes and gives them legitimate work, allowing them to come home. - Slacker Spice
  • It's either hypocritical or ironic (or both) that the head of the Ku Klux Klan sings "O Death" when one considers what the song's about: how death is unbiased and claims everyone, young and old, rich and poor, black and white.
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  • The governor also underscores another Odyssey reference: after Odysseus returns to Ithaca, he has to re-establish his right to rule as king against a populace that resents him for murdering two generations of their sons (first as soldiers to Troy, then as suitors to Penelope). Everett can't be the mayor of his hometown, but he does inadvertently help the governor of Mississippi get reelected. It's the opposite of a Composite Character.
  • There's a joke in this movie so subtle it took me years to realize it, and I'm convinced it goes over most people's heads. The John Goodman character is obviously based on the cyclops. We later find out that he's a member of the Klan. One of the ranks in the Klan is Grand Cyclops.
  • At the climax, Homer Stokes is run out of town on a rail. This is the traditional prelude to being tarred and feathered — ironically, he's going to be lynched himself.
  • Really, the Odyssey references are astounding. The blind seer, the punishment for killing (the Sun god's) cattle, the mysterious and dangerous sirens, animal transformation, Cyclops... even Everett's wife's insistence on having the perfect, precise wedding ring from their old house: Penelope did not believe Odysseus until he proved himself to her by telling the story of how he made their unique and one-of-a-kind wedding bed.
    • There is also the giant wooden cross that defeats Homer Stokes, the grand CYCLOPS...hmmm, now how is the cyclops in the Odyssey defeated?
    • The scene in the movie theater is meant to represent Odysseus' journey to the underworld, where he is given a warning by the spirits of the dead (in this case, Pete, who they previously assumed had been turned into a toad and squashed, warns them not to seek the treasure).
    • The name "Odysseus" (from which we get the term "odyssey") in the original Greek can be roughly translated to "he who endures many hardships," i.e., a man of constant sorrows.note 
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    • The singing women in the river are explicitly called sirens, but they distract the heroes and put them in a stupor, like lotus-eaters.
    Delmar: Them si-reens did this to Pete! They loved 'im up and turned him into a horny toad!
    • They're the sirens. Everett should have tied himself to the steering wheel of the car. They also get a role as Circe, the sorceress who turned men into pigs. The lotus eaters are represented by the people being mass-nbaptized in the river.
    • The KKK rally is the scene where Odysseus and his men have to sneak out of the Cyclops' cave dressed as sheep, and dropping a burning cross onto the one-eyed bible salesman's head is Odysseus using a burning log to gouge out the Cyclops' eye.
    • Baby Face Nelson shooting up random cows ("I hate cows worse'n coppers!") is a reference to Odysseus' sailors slaughtering the cattle of Helios.
    • The name Peter (Pete) means "the rock". The name Delmar means "(of) the sea". Everett is stuck between THE ROCK and THE SEA, referencing Charybdis and Scylla.
    • The old blind prophet represents Homer, the author to whom The Odyssey is attributed, and who was also traditionally depicted as a blind, wandering storyteller. It makes sense that he knows everything that's going to happen in the story: he wrote it! It also makes it a lovely, poignant metaphor to see him vanishing into the distance in the end: once the story's over, he's off in search of the next one.
      • Still more Brilliance: scholars do not know who Homer really was, if he really existed, or even if he was a single person. This is why the old man claims to have no name.
    • Odysseus' enemy was Poseidon, god of the sea, who kept waylaying him on his return voyage home. In the film, Everett's cover story for most of the journey is that they have to reach the treasure before it's washed away by a flood, literally forcing them to race against the waters.
      • Water also shows up at several critical points at the film, threatening to break up the group: Delmar and Pete are lured away by the lotus-eaters when they are baptized in the river, and later, Pete is stolen away by the river-dwelling sirens. It's also not coincidence that the river represents both salvation (baptism) and sin (the seductive sirens).
    • Likewise, Everett and the boys' rescue from drowning seems to be a ridiculous Deus ex Machina...until you remember that the end of The Odyssey was a literal, classical Deus Ex Machina: the squabbling seems poised to go on forever until the goddess Athena shows up and tells everyone to cut it out.
    • The climax of The Odyssey involves Odysseus proving his identity with knowledge/skills only he possesses (showing his father a distinctive scar, describing their marriage bed to his wife). In the film, the boys prove that they're the real Soggy Bottom Boys by singing their signature song, and are rewarded with a pardon (and in Everett's case, by getting his wife back), regaining their lives as free men the same way Odysseus reclaimed his life.
  • The "Soggy Bottom Boys" get literal soggy bottoms when the valley is flooded (it's also a reference to the fact that they were still soaked from their recent baptism).
  • How are the Soggy Bottom Boys so talented at singing right at the beginning? The Soggy Bottom Boys (minus Tommy) worked together on the chain gang for years. As we see in the intro, the chain gang sings work songs together to keep morale up.