Home Free’s “Man Of Constant Sorrow” is nothing but soulful. 

Filmed at Oak Hollow Farm in Fairhope, Alabama, the quintet dug deep into their southern roots to celebrate the song’s rich history. Vocal percussionist and beatboxer Adam Rupp was able to put his extraordinary ability on full display, perfecting unique sound and instruments over twenty years of mastering his craft.

“We’ve taken this song all around the world this past year on tour,” baritone Adam Chance shared with Billboard. “It was inspiring to be able to bring it back home to Alabama and really dig deep into the heart of it for our video.”

Tenor Rob Lundquist further admitted, “I’ve lost count how many times I’ve seen O Brother, Where Art Thou? It definitely put this classic tune on the map for a lot of people, and we sure hope we’ve honored it!”

The Song That Has Seen All The Trouble In The Days

If there’s one word that could be used to describe the song “Man of Constant Sorrow,” it would definitely be timeless. Though most people know the song from the 2000 film O Brother, Where Art Thou? – it actually has a thorough history that goes way back to decades.

Originally titled “Farewell Song,” a blind fiddler player named Dick Burnett wrote and published a folk song in 1913. Little did he know how many changes the song title would go through or how many people would record it.

In 1928, an early version was recorded by Emry Arthur, which gave the song its current titles. Since then, the song has been recorded several times, but The Stanley Brothers became the first ones to achieve real success when they released their recording of “Man of Constant Sorrow” in the 1950s.

“I am a man of constant sorrow, I’ve seen trouble all my days. I bid farewell to old Kentucky, the place where I was born and raised. For six long years, I’ve been in trouble, no pleasures here on earth I found. For in this world I’m bound to ramble, I have no friends to help me now,” the song goes.

How The “Man of Constant Sorrow” Became An Award-Winning Song

However, after it experienced a wave of popularity in the 1960s, the buzz around “Man of Constant Sorrow” somewhat calmed down. But that all changed in the year 2000, when the film O Brother, Where Art Thou? was released. 

The song was an important part of the movie’s plot, as the three main characters recorded it under the guise of a group called the Soggy Bottom Boys. “Man of Constant Sorrow” has been performed at two different points in the film and was even featured on its Grammy-winning soundtrack with lead vocal by Dan Tyminski.

The soundtrack’s version of “Man of Constant Sorrow” received a CMA Award for Single of the Year in 2001 and was also named Song of the Year by the International Bluegrass Music Association. A year later, it won a Grammy for Best Country Collaboration at the 44th Annual Grammy Awards. It peaked at No. 35 on Billboard’s Hot Country Songs chart and managed to sell more than a million copies in the United States by November 2016.

Since then, it seems that interest in the song has been just as strong as ever. An unknown number of artists have covered this timeless tune, including Alison Krauss, Travis Tritt, and Waylon Jennings, among others.

In 2018, Home Free released their moving rendition of “Man of Constant Sorrow” on their album Timeless. Tune in below for the a cappella vocal group’s breathtaking performance.