Country Rewind: Waylon Jennings Once Recorded ‘Man of Constant Sorrow’ Cover

by Clayton Edwards

When you hear the song title, “I’m a Man of Constant Sorrow,” what comes to your mind? If you’re like most people, it’s probably the 2000 film O Brother, Where Art Thou?. The song became a huge hit because of that film. Millions of people have heard that cut of the song which was recorded by Dan Tyminski. On the other hand, if your taste in music leans to the more traditional, you might think of the Stanley Brothers’ version of the song. Did you know that Waylon Jennings also recorded his own cover of the song?

The track was included in Waylon Jennings’ major-label debut album Folk-Country. This was long before Waylon Jennings was a honky-tonk hero. In fact, the album dropped in 1966, seven years before he released the seminal Honky Tonk Heroes album. Back then, Waylon was a young, clean-cut, country singer.

Waylon Jennings’ version of the song sounds completely different than the more popular renditions. In fact, it’s about the only thing it has in common with most versions is the lyrics. The reason behind the huge difference is pretty simple. Waylon was a straight-up country singer. The more popular versions of “I am a Man of Constant Sorrow,” are bluegrass. They combine the sorrow of the lyrics with an up-tempo arrangement to achieve that high-lonesome sound that is almost exclusive to bluegrass. On the other hand, Hoss played it like a sad country song. Check it out below. It’s not what you’re used to. However, you can never go wrong with some Waylon.

Pre-Waylon Jennings Versions of ‘I’m a Man of Constant Sorrow’

Long before Waylon Jennings recorded “I’m a Man of Constant Sorrow,” it was called “Farewell Song.” It was originally published in a songbook composed by Dick Burnett, a fiddler from Kentucky in the 1910s. However, Emry Arthur cut the song in 1928 under the more familiar name.

Interestingly, Waylon Jennings’ version of “I’m a Man of Constant Sorrow,” sounds more like the Emry Arthur version than any other popular rendition. Arthur’s version was a straight-forward sad country song. It featured very basic rhythm guitar and vocals. Waylon’s arrangement of the tune is a little more complicated. However, it is definitely in the same vein as this early recording.

The legendary bluegrass group The Stanley Brothers cut a version of the song that sounds much closer to the popular modern rendition. They recorded the song in 1950 and released it the next year. It was a hit for them. Some would even say that their recording is the definitive version of the song. Check it out and compare it to the cut from the O Brother, Where Art Thou? soundtrack.