Earlier this year, Greensky Bluegrass, one of the marquee acts of the jam-grass scene, headlined the Telluride Bluegrass Festival in Colorado. It was a full-circle moment for the quintet: In 2006, Greensky won the fest’s hard-fought band competition.
“It was such an important landmark in the band’s trajectory,” lead singer Paul Hoffman tells Rolling Stone backstage at Telluride during the group’s 15th appearance at the festival. “[Winning the competition] put a lot of wind in our sails. It felt career-defining to be part of this event.”
Greensky is celebrating 25 years together with their latest album, XXV, a record that celebrates their steady climb over a quarter century from pizza shops and dive bars into arenas.
“I think that’s just the key to the success — I feel at home with our fans,” Hoffman says. “I look out there and I see my people.”
To mark the milestone, Greensky hosted a special two-night run over Halloween weekend at the Wings Event Center in the band’s hometown of Kalamazoo, Michigan. Opening acts included bluegrass mainstay Sam Bush, alongside rising stars Lindsay Lou and Holly Bowling.
“When we were playing the arena, it occurred to me what a great accomplishment to have a 25-year anniversary with these five guys that have been in that band,” Bush says. “It’s a testament to friendship, brotherhood, and the sharing the love of music together.”
Instead of a fresh record of new songs, XXV is a reinterpretation of the group’s large catalog of material. It’s a reimagining of certain signature melodies and deep cuts, selections that best represent the wide gamut of sonic textures and creative avenues that define Greensky.
“We’re always pushing our talent and our ability just a little farther, just to be a little bit uncomfortable,” Hoffman says.
Joining the outfit on this expansive project are an array of musical colleagues that have played significant roles in the backstory of Greensky, including Lou and Billy Strings, who both came up in the same Michigan scene as Greensky.
“Without Greensky Bluegrass, we would not have Billy Strings like the one you know today. He’d tell you the same thing,” Lou says. “[Greensky] has influenced so many of us who have made a home here in the scene.”
When Lou first started playing in the bluegrass circles of Michigan, Greensky had already been established for a decade. By that point, they’d become a prominent national touring act, especially on the festival circuit, and would always give a leg up to fellow artists also emerging from the Great Lakes State.
“The support and inclusion they’ve shown me has been seriously pivotal,” Lou says. “They’ve been such a touchstone of my journey that they really have all become like brothers to me.”
Along with Strings and Lou, Bush, Bowling, Nathaniel Rateliff, Ivan Neville, Aoife O’Donovan, Jennifer Hartswick, and Natalie Cressman all appear on XXV.
“They’ve transcended genre,” O’Donovan says of Greensky. “You’re watching this show with great songwriting, great singing, and great instrumental prowess. It’s a rock show, but it’s not a rock band.”
A prominent figure in Americana, bluegrass, and folk circles, O’Donovan is also a member of Grammy-winning trio I’m With Her. O’Donovan remembers first crossing paths with Greensky almost two decades ago at the Grey Fox Bluegrass Festival in New York, with everyone sitting around the campfire, drinking beers and jamming.
“I feel like they haven’t really changed,” O’Donovan says. “Their sound has evolved, but it’s not wildly different than it was when they started, and I really respect that.”
The Greensky Bluegrass sound is one rooted in freewheeling and fast-paced acoustic music — in the same vein as New Grass Revival, String Cheese Incident, Old & In the Way, or Leftover Salmon.
“In New Grass Revival, people would tell us, ‘That ain’t bluegrass,’ and we would say, ‘We know,’” Bush chuckles. “And I’d like to think Greensky is accomplishing [that, too], what Billy Strings is doing — the progressiveness and rock & roll side of the show.”
Greensky Bluegrass onstage at Red Rocks in Morrison, Colorado. Photo: Dylan Langille*
Formed in Kalamazoo in the fall of 2000, Greensky were initially a ragtag outfit of college kids with an interest in bluegrass music. Hoffman graduated high school, saw famed mandolinist David Grisman at the Hookahville festival in Ohio, and felt inspired enough to buy a mandolin right before he appeared on campus of Western Michigan University as a freshman.
“I didn’t even know what bluegrass was. I had no idea who Bill Monroe was. I didn’t know the context of it all. I was just totally going for it,” Hoffman told The Smoky Mountain News in 2022. “And I still don’t know what bluegrass is, which is why we’re not very bluegrass-y, because we’re just kind of doing our thing. I love playing bluegrass, but it’s not about the bluegrass as much as it’s about this acoustic ensemble thing — the challenge is to be a heavy metal band with a banjo.”
One night in October 2000, Hoffman wandered into the Blue Dolphin, a popular bar for college students in Kalamazoo, for weekly open mic nights. Onstage was guitarist Dave Bruzza and Michael Bont on banjo, who were jamming under the name Greensky Bluegrass. It wasn’t a real or serious group, just a funny name someone came up with.
Hoffman approached Bruzza and Bont and asked if they wanted to get together to jam. Bruzza gave Hoffman his home address and when Hoffman showed up, he essentially never left. Greensky Bluegrass had become solidified.
“Those early years were fun,” Hoffman says. “But, I never imagined it would be this serious or last thing long or that I would build a career on free beer and playing music.”
In the ensuing years, bassist Mike Devol and dobroist Anders Beck would join. From the outset, Greensky was an extremely hungry and determined act. Doing upwards of 200 gigs a year, the band would perform on any stage that would have them.
“Play gigs and go have fun. We hardly got paid,” Hoffman says, laughing. “But we loved it, and I think that’s what kept it going. We’re friends, we’re brothers. We still have fun — that’s the most important thing.”
Eventually, the band members were able to quit their day jobs and pursue music full-time. By 2006, they took home the band competition award in Telluride, which sparked nationwide interest from booking agents and festival promoters.
In the early years of Greensky, Hoffman attributes the group’s rapid-fire reputation as a “must see” live show to the “adrenaline and spirit in the band.” As time has gone along, the members’ quest to discover and explore new musical landscapes, onstage and in the studio, has only grown.
“The thing I love about our band, we have a shared responsibility for the rhythm, the music, the melody,” Hoffman says. “And then, organically, that role shifts throughout all the songs, especially when we’re jamming. It’s just so interesting and challenging.”
Greensky Bluegrass is now in the midst of a tour through the southeast, which wraps Nov. 15 in Miami Beach, Florida. They also just announced a spring 2026 run kicking off April 16 in Wilmington, North Carolina.
“Connecting people who don’t have anything in common except for liking music or liking the experience of our community is such a powerful thing,” Hoffman says. “It’s about so much more than music.”