Celebrity Name: Tim O’Brien
New Company: The Kurland Agency
Primary Agent: Jack Randall
Department: Music Booking
Territory: Worldwide
- Grammy-winning bluegrass legend Tim O’Brien has officially joined The Kurland Agency, with agent Jack Randall handling his worldwide booking representation.
- O’Brien, a West Virginia native with a 50-year career, brings 2 Grammy wins, 7 nominations, and a 2025 IBMA Hall of Fame induction to the deal.
- The signing comes ahead of a major milestone release, The Tim O’Brien Songbook, a collection of 40 original songs dropping May 2026.
- His current album Lonesome Armadillo (Howdy Skies Records) is out now, with active touring expected under the new representation.
Grammy-winning singer-songwriter and multi-instrumentalist Tim O’Brien has signed with The Kurland Agency for worldwide booking representation, with agent Jack Randall leading the partnership. The Kurland Agency made the announcement via their official Instagram.
Born in Wheeling, West Virginia in 1954, O’Brien built one of American roots music’s most respected careers from the ground up. After seeing Doc Watson on TV as a kid, he became a lifelong devotee of old-time and bluegrass music, and hasn’t looked back since.
He burst onto the national scene in 1978 as a co-founder of the Colorado bluegrass band Hot Rize, writing songs that would go on to define the genre.
O’Brien’s pen proved just as powerful as his picking. His tunes “Walk the Way the Wind Blows” and “Untold Stories” became hits for Kathy Mattea, and his catalog has since been covered by Garth Brooks, Nickel Creek, and The Dixie Chicks.
Living in Nashville since 1996, he’s become a go-to session player on guitar, mandolin, fiddle, and banjo; collaborating with Steve Earle, Mark Knopfler, Sturgill Simpson, Billy Strings, and even The Chieftains.
The accolades tell the full story: 2 Grammy wins, 7 nominations, IBMA Best Male Vocalist in both 1993 and 2006, IBMA Song of the Year (2006), induction into the West Virginia Music Hall of Fame (2013), the Colorado Music Hall of Fame in 2022 with Hot Rize, and most recently, the IBMA Hall of Fame in 2025.
The timing of this signing couldn’t be better. His current album Lonesome Armadillo is out now on Howdy Skies Records, and The Tim O’Brien Songbook (collecting 40 originals from his 50+ year career), drops in May 2026.
This signing follows a wave of notable artist representation moves in 2026, including country star Keith Urban signing with Crush Management and rising talent Mary Kutter signing with WME.
This signing is more than a business transaction, it’s a statement. The Kurland Agency is one of the most trusted names in folk and roots music booking, and adding a Hall of Famer like Tim O’Brien to their lineup strengthens their roster considerably.
For O’Brien, the move is perfectly timed: a fresh Hall of Fame badge from 2025, a live album in the market, and a career-defining songbook on the horizon gives his new agent serious ammunition heading into 2026’s festival and touring season. This is what smart career management looks like at the highest level.
Will The Kurland Agency unlock bigger festival slots and international touring opportunities for O’Brien in 2026? What other roots artists would you like to see make a similar representation move?
