Top 5 Versions of “Man of Constant Sorrow” (1928 – Present)

We first heard George Clooney’s new song “Man of Constant Sorrow” in O Brother Where Art Thou?  and a new world of music was opened to the masses. We only later found out the song was neither new nor sung by George Clooney. Clooney was lipping over the flawless high lonesome chops of Dan Tyminski (of Allison Krauss and “Hey Brother” fame).

The song was first published in 1913 (by blind Kentucky fiddler Dick Burnett that he titled “Farewell Song” in the songbook “Songs Sung By R. D. BURNETT. The blind man”) and the first recorded version was 1928 Emry Arthur. Here are the top 5 versions of the “Man of Constant Sorrow”:

5. Emry Arthur (1928)

This is the first known recorded version of the song. And, fun fact: That’s Dock Boggs on the banjo.

4. Roscoe Holcomb (1962)

Everyone else who has done this song, or will do this song is a poser in comparison with Roscoe Holcomb. Roscoe was, first of all, named Roscoe (as in, thats no “stage name”) and second is the fact that Roscoe was a full on Kentucky Coal Miner and didn’t even record util he was an old man. And Roscoe is whom, by the way, Bob Dylan probably leaned the song.

3. Dwight Yoakum (2015)

Everything Dwight Yoakum does is perfect. Including his version of “Man of Constant Sorrow” (and yes, Dwight is a Bakersfield boy, but by way of old Kentucky).

2. The Stanley Brothers & The Clinch Mountain Boys (1951)

The first recording was 1928 then we have about a 30 year gap until the next known version hits in 1951 from the brothers Stanley. Ralph Stanley (one of the Stanley Brothers) also sang in O Brother Where Art Thou? with his haunting version of “O Death“.

1. Dan Tyminski (AKA “Soggy Bottom Boys”)

Dan Tymisnki, of Allison Krauss + The Union Station, provided the vocals for the O Brother Where Art Thou version (and, I do want to add, that Dany Tyminski looks like the super nice uncle in your family who would loan you his Ford Ranger for up to 6 months and wouldn’t care if you just kept it and never said a word about it). Here he is doing a live version of “Man of Constant Sorrow” (in Kentucky). NOTE: Below that video is one Dan Tyminski where teamed up with the late Avicii churning the toe-tapping track that is “Hey Brother”

Honorable/Dishonorable Mentions:

Miley Cyrus gives it a go at the George Clooney tribute (I will say, however, her version of Dolly Parton’s Jolene is priceless).

Waylon Jennings (when he still had a pompadour).

Obligatory Dylan version for your listening pleasure (?) here.

For more on the story of “In Constant Sorrow” check out here, here and here.


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