A sold-out crowd packed the Grand Ole Opry House in Nashville on Saturday for a one-night-only concert marking the 25th anniversary of the O Brother, Where Art Thou? soundtrack—one of the most consequential recordings in the history of American roots music.

Headlined by Billy Strings, Alison Krauss, Dan Tyminski, Emmylou Harris, and Del McCoury, the evening drew together artists from the original 2000 T Bone Burnett-produced soundtrack alongside a new generation of performers who have carried its legacy forward. The full lineup included Chris Thomas King, the Fairfield Four, the Whites, Tim Blake Nelson, Old Crow Medicine Show, Molly Tuttle, Sarah Jarosz, Jerry Douglas, Colin Linden, the Fisk Jubilee Singers, the Alaskan Sunnyside Sisters, and more—all performing around a single microphone in the classic style.

The O Brother soundtrack, released alongside the Coen Brothers‘ Depression-era odyssey starring George Clooney, John Turturro, and Nelson, spent 683 weeks on the Billboard 200, topped the chart, and won the Grammy for Album of the Year in 2002. It was also named Album of the Year at the CMA Awards, ACM Awards, and the IBMA Bluegrass Music Awards. More than a commercial triumph, the record is widely credited with sparking a mainstream revival of bluegrass, folk, gospel, and old-time country at the turn of the century—a revival whose influence is still being felt today.

 

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Krauss and the Fairfield Four opened the evening, setting a reverent tone, and Krauss later brought the house to its feet on “Down to the River to Pray” joined by the dozen members of the Fisk Jubilee Singers. Harris and Tuttle joined her for an a cappella rendition of “Didn’t Leave Nobody But the Baby”—a trio that echoed the original’s legendary pairing of Harris, Krauss, and Gillian Welch. Old Crow Medicine Show blazed through “Big Rock Candy Mountain”, Sarah Jarosz led the crowd through “You Are My Sunshine”, and the Whites offered a heartfelt take on “Keep On the Sunny Side”.

One of the night’s most memorable moments came when Strings and Tyminski shared the mic for “O Death”—Strings stepping into the role made famous on the soundtrack by Ralph Stanley, with Tyminski, who was famously George Clooney‘s singing voice on “Man of Constant Sorrow”, alongside him.

The evening had a particular resonance for Strings, who staged his own full-scale theatrical tribute to O Brother, Where Art Thou? on Halloween in 2024 at Baltimore’s CFG Bank Arena—a production dubbed “O Billy, Where Art Thou?” that featured elaborate costumes, narrative staging, and a cast that included Nelson, King, Douglas, and Burnett himself. The show wound through the film’s storyline scene by scene, incorporating original songs, covers, and most of the iconic soundtrack alongside unexpected detours into Led Zeppelin, Black Sabbath, Steve Miller Band, and Johnny Cash. Strings’ 2024 album Highway Prayers also became the first bluegrass album to top the Billboard album sales chart since the O Brother soundtrack did so in 2002.

The night ended with the full cast assembled onstage for a reprise of “I’ll Fly Away”, followed by a Q&A.

 

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During the Q&A, Tyminski reflected on the soundtrack’s lasting impact. “This music owes a huge debt to O Brother, Where Art Thou?” he said. Burnett then spoke to the enduring power of American roots music itself:

“I hear bad things about our country,” he said, “but if you want to know what’s good about the United States, listen to our music, because the music in the United States is the best music in the world. People have come from all over the world in different languages, different religions, different politics, different all of it. But the musicians have all listened to each other and we’ve made harmony.”

Check out fan-shot videos from the O Brother, Where Art Thou? 25th anniversary celebration below.

Alison Krauss & The Fairfield Four – “Every Time I Feel The Spirit” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Old Crow Medicine Show – “Big Rock Candy Mountain” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Alison Krauss & The Fisk Jubilee Singers – “Down to the River to Pray” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Emmylou Harris, Molly Tuttle & Alison Krauss – “Didn’t Leave Nobody But the Baby” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Del McCoury Band – “Get Down On Your Knees And Pray” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Tim Blake Nelson – “In the Jailhouse Now” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Sarah Jarosz – “You Are My Sunshine” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Dan Tyminski – “I Am a Man of Constant Sorrow” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Del McCoury Band, Billy Strings, Dan Tyminski, Molly Tuttle & More – “I’ll Fly Away” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Chris Thomas King & Colin Linden – “Hard Time Killing Floor Blues” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Billy Strings – “Wild Bill Jones” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Molly Tuttle – “I Am Weary (Let Me Rest)” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Molly Tuttle & Sarah Jarosz – “I’ll Fly Away” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Dan Tyminski & Billy Strings – “O Death” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Del McCoury Band, Billy Strings, Molly Tuttle, More – “Angel Band” – 2/28/26

[Video: Ohio Grown Live Music Archive]

Alaskan Sunnyside Sisters – “In the Highways” – 2/28/26

[Video: Ohio Grown Live Music Archive]