On Saturday, February 28, the Grand Ole Opry tipped its hat to the music-driven satirical comedy-drama O Brother, Where Art Thou, with a fierce lineup of trusted artists and movie associates delivering incantations of classic material from the film. The event marked a significant 25-year milestone since the film graced the big screen, rekindling appreciation and fondness for the bluegrass canon and timeless music. 

The lineup included prominent voices from the movie and those associated with the musical deliveries on the film’s compilation soundtrack, Emmylou Harris, Dan Tyminski, and Alison Krauss, as well as the next generation of bluegrass practitioners and carriers of the craft, Billy Strings, Molly Tuttle, and Sarah Jarosz. 

Seasoned veterans of the genre, like Del McCoury Band, Old Crow Medicine Show, and others, also participated in the one-night-only event, igniting beloved covers like “Big Rock Candy Mountain.” During the night, Krauss reprised her soundtrack contribution with an a cappella delivery of “Down to the River to Pray,” with help from The Fisk Jubilee Singers. She also tapped Harris and Tuttle, who stepped in for the film’s original songstress Gillian Welch, for the traditional, “Didn’t Leave Nobody But Baby.” 

Top moments also included Tyminski’s delivery of the film’s musical backbone, “I Am a Man of Constant Sorrow.” He also teamed up with Strings for a hair-raising take on “O Death.” Strings also turned out “Wild Bill Jones.” Notably, the artist put on his own retelling of the film during his 2024 Halloween soiree. [Read the recap here.] 

Strings, along with a heavy lineup of talent, also came together for big band takes on “I’ll Fly Away” and “Angel Band.” The latter included an appearance from T Bone Burnett, the Grammy-winning producer of the film’s soundtrack. 

Following last night’s remarkable performance, videos surfaced online providing a taste of the celebratory occasion in Nashville. Watch below.