Ranking Bob Dylan Songs, #97: Man of Constant Sorrow

I want to like this song more than I actually do. Of all the songs Dylan recorded on this album, “Man of Constant Sorrow” is one of the most notable and most recognizable. Listeners of today are most likely to recognize the Soggy Bottom Boys rendition from the Coen Brothers’ 2000 film, O Brother, Where Art Thou?, but there are dozens of other famous versions recorded since it was (allegedly) written by Dick Burnett in about 1913. It’s easy to understand why this song has been performed so many times—there is a playful poetry and malleability to its lyrics. Even the phrase “man of constant sorrow” is particularly lyrical, falling naturally into trochaic feet. And the story told by the song—about a man of humble origins venturing out into the cruel, cold world—is the kind of archetypal material that folk musicians flock to.

The beginning of Dylan’s version does capture a sense of stoic despair that the song calls for. There is a poignant perseverance in the way he opens with, “I am a man of constant sorrow/I have seen trouble all my days.” Dylan’s voice remains gentle and delicate throughout the song.

At the same time, this restraint, in both his voice and his guitar playing, combined with his decision to hold particular notes much longer than they ought to be held, lend a feeling of monotony to the song. As a result, the song feels a lot longer than the three minutes it actually runs. It probably made sense to Dylan to perform a song about constant sorrow in a way that captured a feeling of monotony and loneliness, but it actually misses the point. The version performed by the Soggy Bottom Boys, as well as most of the bluegrass versions available on YouTube, captures the sense of rambling and adventure in the song. These versions are much more fun and intriguing than Dylan’s own version.

The truth is that the song doesn’t really play well to Dylan’s vocal strengths; his voice is not nearly smooth enough to sing a song like this with restraint AND excitement. With that said, Dylan does of course have a knack for the poetry behind the song, and the first minute of “Man of Constant Sorrow” is one of the highlights of Dylan’s first album.

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