When George Clooney sings into his mic as the character Ulysses Everett McGill in the Coen Brothers film O Brother, Where Art Thou? (2000)—a member of the film’s impromptu band of bandits, the Soggy Bottom Boys—he takes a hopeful step up to the mic. Widemouthed, an infectious, drone-like bluegrass tune called “I Am a Man of Constant Sorrow” spills out of him.
Except it’s not Clooney’s voice. It’s Dan Tyminski’s, the bluegrass singer and instrumentalist whose reputation was on the rise as part of Alison Krauss’ Grammy Award-winning band Union Station. It was a life-changing moment that propelled Tyminski’s already successful career but also helped revive the bluegrass genre for contemporary audiences.
Tyminski—who just earned another 2025 Grammy Award nomination with his latest album Live from the Ryman, which may increase his prior 14 Grammy wins—will perform on the Eastman Presents series this Saturday, November 16 at 7:30 p.m. in Kilbourn Hall.
The story of O Brother goes that Clooney, who was supposed to sing the tune but had doubts about his vocal abilities, made a deal with Tyminski, a member of the band providing support. “I’ll act, you sing,” Clooney said to Tyminski.
Tyminski was initially upset that he missed out on his chance to record with Clooney, and he worried it would be obvious that Clooney wasn’t the one singing. But the feeling didn’t last long when the film became a sensation—Clooney won a Golden Globe for his performance; the album of O Brother won multiple Grammy’s, including for Album of the Year—and the royalties started streaming in.
“Had Clooney sang that song, I would have made my $365 for the session fee, and I would have been more than happy, and I would have told the world about how proud I was that I recorded with George Clooney,” says Tyminski. “But because George let me sing that song and didn’t sing it himself, I got to then go home and pay off my house and buy new cars and put my kids through school.”
And no, he says he doesn’t get tired of talking about something that earned him and his family security—and which earned bluegrass music a new audience. “It was a shot in the arm that the music really did need.”
But Tyminski has always been about the music, and so even after O Brother fame, he went along as he had before: performing and touring with Krauss and Union Station. “And honestly, I was so happy and so content with how my career was going, I never made a change for the next 15,” he says.
Tyminski grew up in Vermont, where there wasn’t a lot of bluegrass music around, but remembers playing pinball machines as a young kid in the country music bars his parents would take him to. And soon they discovered a bluegrass festival where they camped out for two nights. Tyminski was instantly hooked for the sense of community he found there.
“My first jam session, I think I was maybe six years old,” he remembers. “I was just playing a little Jew’s harp on my mouth. I didn’t know how to really play any instrument yet. But I stood in a crowd of people, and they were picking songs and they welcomed me in. I just felt like I was accepted, and I belonged at the very earliest age.”
From there, he just kept on going to bluegrass festivals, learning how to play music through the act itself. He started touring as a 19-year-old, first with a band created with his brother in the early ‘80s, and then with one called the Lonesome River Band. In 1992 he joined Krauss and Union Station, where he spent the rest of career—until recently. His last tour with Union Station was in 2015, and he’s since dedicated himself to his own band: the Dan Tyminski Band.
The ushering of any traditional form of music into contemporary contexts is almost always marked by debates around authenticity. Union Station, as well as Tyminsky’s own musical endeavors, is considered part of a progressive movement in the bluegrass genre. But what does that mean?
“Contemporary bluegrass and traditional bluegrass, there’s not a large degree of separation. In my opinion, good traditional bluegrass can be interpreted either way, depending on who’s playing it,” he says. “So, contemporary bluegrass, that’s just what we’re listening to today, because it’s right now.”
In a joke that’s not a joke, he says, “It’s just probably a little more in tune than the old style.”
“When you think of bluegrass music, it’s very easy to think of the hay bale and the straw hat, and you’re musically plinking on a banjo, right? But I think people that aren’t into the music are really not aware that it is so much more than that. The nuance and the subtleties that go into it are kind of mind blowing.”
When asked what it’s like to play in venues like Eastman, a place of formalized music learning and performance, he says it’s intimidating.
“I’m not a very educated musician, but I’m a passionate player,” he says. “I’ve played my whole life, and what I love to do is offer it to other people. Performing, I discovered through a lifetime of playing music, that’s right where I think I shine. It’s where I have the most fun. It’s where I feel like I’m the most effective, playing music where I get to actually communicate to a live audience.”
Audiences, he says, usually respond with jaws dropped.
“So, to play the music school where we have people who love music but aren’t necessarily interested in bluegrass, I look at this as the biggest opportunity that I could have.”
Dan Tyminski Band
Presented in partnership with WRUR Rochester
Saturday, November 16
7:30 p.m. | Kilbourn Hall
Tickets can be purchased through the Eastman Theatre Box Office