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  • From Hyden, Kentucky (Lives in Portland, Tennessee)
  • The elder of the Osborne Brothers, he formed his own band The Rocky Top Xpress, after brother Sonny retired in 2004.
  • He is the only bluegrass artist (so far) to be elected twice into the Bluegrass Music Hall of Fame (as a member of the Osborne Brothers and also as a member of the Lonesome Pine Fiddlers.)
  • 2001, released a duet album with Jesse McReynolds Masters of the Mandolin (Pinecastle).
  • 2006, was appointed to a professorship at Hazard Community & Technical College in Hyden, Kentucky (his home town), teaching music.
  • Songwriting credits include: Bluegrass Express, Big Spike Hammer, Memories, I’ll Be All Right Tomorrow, Son of a Sawmill Man, Pain in My Heart and This Heart of Mine Can Never Say GoodBye.
  • His son Bobby Osborne Jr. is a member of his band, known as “Boj.”
  • 2007, released Bluegrass Melodies album (Rounder).
  • 2009, released Bluegrass & Beyond album (Rounder).
  • 2010, released Memories album (Rural Rhythm), celebrating Bobby’s 60 years in bluegrass music.
  • 2012, released New Bluegrass & Old Heartaches album (Rural Rhythm).
  • 2017, released Original album (Compass), produced by Alison Brown.
  • 2017, won IBMA Award for Recorded Event of the Year (for “Gotta Get a Message to You” from his album Original on Compass Records).
Artist List

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