- Awesome Music: "Man of Constant Sorrow". That is some mighty fine a-pickin' and a-singin'!
- Many people felt that the whole soundtrack was better than the movie. Even people who thought the movie was very, very good. Not only did the soundtrack album get sequels of its own, but it also won Album of the Year at the 2002 Grammys.
- And the a capella singing of "Down to the River" deserves special mention for its INCREDIBLE harmonies. That many people singing together, all with amazing voices, is enough to give you goosebumps.
- Also the a cappella singing of American folk song O Death by Ralph Stanley. The soundtrack producer T-Bone Burnett originally wanted it sung traditionally, till Stanley asked to let him sing it how he wanted to, at which point Stanley put down his banjo and just sang. After about two or three verses, Burnett just said thats it. It also won Stanley the Grammy Award for Best Male Country Vocal Performance in 2002.
- Crosses the Line Twice:
- Everett effortlessly grifting the blind radio station manager into paying double for their performance:"Would it be okay if Mert and Aloysius signed their names with X's? Only four of us can write."
- Everett's daughters telling him repeatedly, directly to his face, that he died from being hit by a train.
- "Oh George, not the livestock!"
- The Ku Klux Klan scene, wherein we learn that Homer Stokes is actually an Imperial Wizard. And so is his little person! The Wizard of Oz antics are also a good laugh in the middle of an otherwise terrifying scene.
- Everett effortlessly grifting the blind radio station manager into paying double for their performance:
- Designated Villain: Vernon T. Waldrip, Penny's suitor, is meant to be viewed in a negative light, given how he's standing in the way of Everett's goal to reunite with his family. In retrospect, however, Vernon stands out as one of the more upstanding members of the cast. He's described as a "bona fide", hard-working man who's willing to marry a divorcee and provide support for her seven children. His fight with Everett is done in self-defense after the latter throws the first punch. Furthermore, he displays a strong sense of professional ethics when he refuses Pappy O'Daniel's offer to backstab his current client in favor of managing O'Daniel's political campaign. The most egregious thing that he does is alert his boss Homer Stokes, a Ku Klux Klan member, to the knowledge that the three main characters are escaped convicts (which they are).
- However...considering his lack of reaction to Homer Stokes' confession, he either already knew about Stokes being with the Klan or doesn't consider it an issue. It's ambiguous whether Waldrip shares Stokes' racism and is simply engaging in Pragmatic Villainy to help his boss, or if he's simply misguided in his loyalties.
- Hilarious in Hindsight: Wayne Duvall, who plays Homer Stokes — the Ku Klux Klan's Imperial Wizard — would later go on to play Senator Benjamin Wade, a radical abolitionist and civil rights activist, in Lincoln.
- Ho Yay: Delmar and Pete are handsy towards each other throughout the movie.
- Jerkass Woobie: George Nelson is presented this way; a lonely man with poor impulse control and a desperate desire for attention and fame, which all drives him to commit crimes. He may also have some bipolar tendencies.
- Nightmare Fuel: The Ku Klux Klan rally is absolutely terrifying.
- Tear Jerker: Tommy's reaction as he's about to be lynched. He believes it's the Devil's way of collecting on his debt, but at the same time he doesn't understand why the Klansmen are dragging him to his death when he hadn't done anything to cross them other than not be their favorite color:"I ain't never harmed you gentlemen. Either one of you... I ain't never harmed nobody!"
- Vindicated by History: It's kind of in the process of this currently. Some Coen Brothers fans still give this a mixed review, while more and more are starting to see it as a masterpiece. There is a growing base that calls it the Coens' finest film.
- Why Would Anyone Take Her Back?: Penny is a shrill, demanding woman who lies to her daughters about their father right in front of him, shows him no loyalty or affection throughout the entire movie, and refuses to remarry him unless he retrieves her old wedding ring in the cabin that is now underwater. Not that Everett is exactly an upstanding citizen himself, but he must really love his daughters if he's willing to put up with that. Although her standoffish behavior may be a reaction to having to put up with Everett's selfish, scheming ways the entire time they were married.
YMMV / O Brother, Where Art Thou?