The biggest thing that struck me while watching O Brother, Where Art Thou? was it's incredible soundtrack. Without the music, the movie would be pretty generic and not as memorable. "A Man of Constant Sorrow" itself was the thing that made the movie great for me.
From the very first time it was played in the movie it caught my attention. Maybe it was George Clooney's amazing voice combined with the awesome harmony by Tim Blake Nelson and John Turturro, but I no longer felt satisfied with any dialogue and just longed to hear the song again.
The first verse reveals Everett's background and gives the audience some insight into his character and puts his character into context without any cheesy dialogue.
I am a man of constant sorrow
I've seen trouble all my days
I bid farewell to ol' Kentucky
The place where I was born and raised
The second verse, though, brings in a deeper meaning which is later confirmed with the plot of the movie.
For six long years I've been in trouble
No pleasure here on earth I've found
For in this world, I'm bound to ramble
I have no friends to help me now
Here the audience learns how long Everett has been in jail and again the idea of a man in constant sorrow is supported. The last line ends up being a major plot point in the movie; when Everett reveals to Pete and Delmar that there is no treasure and in fact, he tricked them because they were chained together. Before Everett revealed his deception, Pete exclaims, “You boys're true friends! … You're m'boon companions!” But as soon as Pete realizes how selfish Everett is, both Pete and Delmar plan to abandon Everett, leaving him friendless.
The next three verses are seemingly addressed at Penny and foreshadow the plot of the movie.
It's fair thee well, my old true lover
I never expect to see you again
For I'm bound to ride that Northern Railroad
Perhaps I'll die upon this train
You can bury me in some deep valley
For many years where I may lay
And you may learn to love another
While I am sleeping in my grave
Maybe your friends think I'm just a stranger
My face you never will see no more
But there is one promise that is given
I'll meet you on Gods golden shore
In these lines, Everett addresses his lover, Penny, and he almost seems to know that she has moved on and told everyone that he has died. The fourth line is quite ironic therefore, because Penny tells everyone Everett was run over by a train. The second of these stanzas describes Penny’s infidelity while Everett “is sleeping in his grave” the “deep valley” being the fake story of his death. The final stanza brings all of the foreshadowing and irony together into one scene when Everett sings the song in the climax of the movie, and gives a quick tug to the fake beard as he sings the word “stranger” making sure that Penny knows that no matter what, he will come through.
“A Man of Constant Sorrow” plays a major role in the plot of O Brother, Where Art Thou? and reveals a lot of the plot in an obvious yet obscure way, and it is also extremely catchy and brings a fun and upbeat tone to the movie.