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  • From Wheeling, West Virginia. Lives in Nashville.
  • A singer/songwriter and multi-instrumentalist (primarily mandolin and fiddle) who rose to prominence with the Colorado-based group Hot Rize (1979-1990). Since then, he has performed as a solo artist and with his band The O’Boys. He has also toured and recorded with his sister Mollie O’Brien, Darrell Scott, New Grange, the Earls of Leicester and several other ensembles.
  • Early years: had a group in high school called the Northern Valley Boys (in high school). He also performed as a solo act in a pizza parlor in Jackson Hole, Wyoming and spent some time as a member of the The Hutchison Brothers, an Ohio group. After moving to Colorado, he worked with a group called Ophelia Swing Band.
  • He plays the role of Red Knuckles in the Hot Rize western band “Red Knuckles and the Trailblazers.”
  • 1984, released Hard Year Blues album (Flying Fish).
  • 1990, sang duo with Kathy Mattea on “The Battle Hymn of Love” a #1 record.
  • Has also sung and played on albums by Mary Chapin Carpenter.
  • 1990, signed by RCA Records but was subsequently dropped due to budget cuts by the label before his first album was released.
  • 1991, released Odd Man In album (Sugar Hill).
  • 1993, released Oh Boy! O’Boy! album (Sugar Hill).
  • 1995, his song “You Love Me, You Love Me Not” was recorded by country singer Hal Ketchum.
  • 1996, released an album of Bob Dylan songs Red On Blonde (Sugar Hill).
  • 1997, became the first artist to achieve three #1 albums on the Gavin “Americana” Charts.
  • 1997, released When No One’s Around album (Sugar Hill).
  • 1997, Garth Brooks recorded a song co-written by Tim called “When There’s No One Around.”
  • 1998, performed with Jeff White, Charlie Cushman, Mark Schatz and Jerry Douglas in a group called “The Flattheads.”
  • 1999, formed a group with Darol Anger, Mike Marshall and Alison Brown called New Grange.
  • 1999, released an album of Irish music The Crossing (Allulu).
  • 2000, began recording and touring as a duo with guitarist/songwriter Darrell Scott.
  • 2001, was appointed president of the IBMA. Resigned two years later.
  • 2002, released Two Journeys album (Sugar Hill).
  • 2003, released Traveler album (Sugar Hill).
  • 2006, won Grammy Award for Best Traditional Folk Recording.
  • 2006, won his second IBMA Award for Male Vocalist of the Year (also won in 1993).
  • 2005, released Real Time album with Darrell Scott (Full Skies).
  • 2005, released Fiddler’s Green album (Sugar Hill). He won a Grammy Award for this album in the categor “Best Traditional Folk Album.”
  • 2006, won IBMA award for Song of the Year (“Look Down that Lonesome Road”).
  • 2012, released We’re Usually A Lot Better Than This album with Darrell Scott (Full Skies).
  • 2013, was a founding member of the Earls of Leicester. He won a Grammy Award for the band’s self-titled album.
  • 2013 was inducted into the West Virginia Music Hall of Fame.
  • 2013, released Memories & Moments album with Darrell Scott (Full Skies).
  • 2013, released new Hot Rize album When I’m Free and began touring once again with the group.
  • 2015, released Pompadour album (Howdy Skies).
  • 2017, released Where the River Meets the Road album (Howdy Skies).
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