Ranking All the Songs from The O Brother Where art Thou Soundtrack

Alison Krauss

“Oh Brother Where Art Thou” is a movie that came out in December of 2000. Starring George Clooney, it is widely regarded as both a crime story and a musical, something that you don’t really see all that often. In the film, Clooney’s character is sent to a chain gang and it isn’t exactly something that he’s adjusting well to. He and a couple of the other individuals on the same chain gang eventually decide to escape from prison and spend their life on the run, all in an attempt to find some type of happiness or at least find some peace. Throughout the movie’s 1 hour and 46 minute run time, the story is told in both word and song. In fact, there are 19 tracks on the soundtrack, all of which are ranked below from number 19 all the way to number one. If you haven’t ever seen the film before, you’d be doing yourself a favor if you clicked on a YouTube link or two, all of which are attached to the song titles. You might find some new music that you really enjoy. Who knows, you might even decide to watch the film for yourself.

19. Angel Band (Ralph Stanley)


Imagine listening to a band full of angels play the most enchanting music that you’ve ever heard. If you can allow your mind to go there, then you already have an idea what the song sounds like. Much of the film involves themes about finding one’s spiritual side and connecting with it. This is a song that is melancholy enough to be performed at someone’s funeral, yet also inspiring enough to help you connect with a Higher Power, even if you don’t tend to consider yourself a believer.

18. Lonesome Valley (The Fairfield Four)


Much of the story in the movie is about being lonely, but not because there are no people around. It’s about being lonely inside of oneself. That’s exactly what this particular song reflects. Anyone who’s ever felt that sense of being lost and not knowing what to do next will understand it.

17. I Am a Man of Constant Sorrow (Soggy Bottom Boys)


This is a theme that runs right the way throughout the film and it shows up on the soundtrack a number of times. It is a song that tries to express the feeling that people often have when they simply don’t know where else to turn. When you feel like everything is turning in on you and you have nowhere to go, it’s often a very lonely and scary place. That’s what this song is about.

16. O Death (Ralph Stanley)


Here you have a song about someone who is so unhappy that they actually want death to come and get them so they won’t have to suffer anymore. It’s a very dark place to be in. It’s also a place that a lot of individuals have experienced and can therefore identify with.

15. I Am Weary (Let Me Rest) (The Cox Family)


This is a song that is crying out to God. The lyrics describe being so weary that it feels impossible to go on and in those lyrics, the individual in question is begging for some type of respite from it all. It is that type of desperation that you feel where you begin to fervently pray, even if you’ve never prayed before in your life.

14. Didn’t Leave Nobody but the Baby (Allison Krauss, Emmylou Harris, Gillian Welch)



This is another sad song that talks about things like loss, grief and the fact that life can be very unfair sometimes. It’s definitely not a song that will make you feel like skipping home, but it is one that most people probably need to hear in order to help them keep things in perspective.

13. Keep on the Sunny Side (The Whites)


Here you have the polar opposite of the song listed in the above paragraph. It is one about looking for the positive things, even when it seems like there aren’t that many positive things to look for. It talks about never giving up, always looking for the silver lining and going at it again with each new day, even when you got kicked in the teeth the day before.

12. Hard Time Killing Floor Blues (Chris Thomas King)


It wouldn’t hardly be a prison musical without some type of song that relates directly to the types of feelings that are often experienced when one is in prison. Some of the song is meant to be tongue-and-cheek and other parts of it are more serious. There’s no doubt that when you listen to it, you’ll laugh out loud at some verses and then you might find yourself crying during others.

11. Down to the River to Pray (Alison Krauss)


This is the song that talks about struggling with understanding why things have to be the way they are. As a result, the person in the song goes to the river in order to pray about these things in hopes of finding some type of enlightenment that makes it all the easier to understand.

10. The Big Rock Candy Mountains (Harry McClintock)


This song is sort of like ‘Hard time Killing Floor Blues,” only it’s a song that is meant for the part of the film after they’ve escaped and they’re trying to find some semblance of freedom. If you’ve ever looked forward to something in order to get you through a hard time, then you will probably understand where the song fits in the grand scheme of things.

9. Indian War Whoop (John Hartford)


This is an instrumental song and just as the name implies, it’s all about trying to outrun some type of battle. Some people celebrate these battles and others can’t stand them. This is a song that walks that fine line between these two camps, largely in hopes of helping the audience understand both sides a little better.

8. In the Jailhouse Now (Tim Blake Nelson)


Again, it would be hard to have some type of jailhouse prison musical without songs about being in jail. This is another song that talks about what it’s like to be in jail and the lifestyle that is often experienced by people there.

7. I Am a Man of Constant Sorrow (John Hartford)


Here you have the instrumental version of the same song that appears several other times on the soundtrack. There’s no doubt about it, instrumental songs hit differently than songs with vocals, even when you’re listening to the same song. As a result, a lot of people focus more on the music here because it’s easier to focus on the way the music moves throughout the song when you’re not distracted by the lyrics.

6. In the Highways (Leah Peasall)


Here you have another song about looking to something better, even in the face of a tremendous amount of adversity. It’s a song that’s all about surviving the here and now and then hoping that things will be better in the long run.

5. I’ll Fly Away (Allison Krauss, The Kossoy Sisters)


This has been one of the most celebrated spiritual songs for decades. It talks about flying away from all of the trials and tribulations of this world when one dies in order to experience the glory of being in Heaven.

4. I Am a Man of Constant Sorrow (Norman Blake)


This is another instrumental version of the song performed by someone else. It’s also featured only on the deluxe edition of the soundtrack, not on the standard edition. If you’re a true fan of the film or you really like the music (and you purchase the deluxe edition), you’re likely to notice several different versions of this song, some with vocals and some without.

3. I Am a Man of Constant Sorrow (Dan Tyminski)


Here you have an acoustic version of the song which provides a slightly different take on it. In addition, it’s performed by a different artist. Since every artist typically brings their own performance style, it gives you an opportunity to listen to the same song in a completely different manner. There’s no doubt about it, it tends to hit differently every time you listen to it on the soundtrack.

2. You Are My Sunshine (Norman Blake)


This is another song that people have heard for decades. It’s a song about loving someone so much that they literally become your light in the world. At the same time, you’re absolutely begging God not to take that person away because if that were to happen, there would be no further point in living.

1. Po Lazarus (James Carter)


You might remember that Lazarus was the person who died and then was resurrected. This is the song that laments that individual because things aren’t always kind in this world. There are times when people are so unhappy that they consider death a respite. Therefore, the very idea of being resurrected right back into the middle of it all might be one of the worst things a person could think of.

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