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Born in Leslie County, Kentucky, Osborne is known primarily for his collaborations with his brother Sonny Osborne in their band, the Osborne Brothers. Osborne grew up helping his dad stock his granddad's general store and absorbing the songs on the Grand Ole Opry, eventually dropping out of high school to form a band with his brother, Sonny. He was a pioneer in conceiving the now-popular high lead vocal trio concept. He has released many recordings since the 1950s. The Osborne Brothers recordings of "Rocky Top", and "Kentucky" were named official state songs of Tennessee and Kentucky, respectively. Osborne was drafted into the U.S. Marine Corps in 1951 and while serving in the Korean War he was wounded in action and received the Purple Heart.
"Bobby knew nothing about bluegrass music. He was listening to the Grand Ole Opry one night on WSM radio. He liked the sound of that banjo, and found out later on it was Earl Scruggs playing a tune called “Cumberland Gap.” From then on, he became interested in that music". He appeared on many shows with his musical hero, Ernest Tubb, playing guitar and singing. Ernest Tubb suggested that Bobby play the mandolin to complement his high tenor voice. He began to play the mandolin and it remained one of his main instruments for the rest of his career.
The Osborne Brothers were made Grand Ole Opry members in 1964, and were inducted into the International Bluegrass Music Hall of Honor in 1994. Bobby now gives mandolin lessons at the Kentucky School of Bluegrass and Traditional Music in his home town Hyden, Kentucky.
In 2017 Bobby released a solo album called ORIGINAL. It was the first album since 2009's Bluegrass & Beyond. The album came about when, at 85 years of age he did a guest collaboration with Peter Rowan which led him to team up with Alison Brown and Compass Records to create music once more. Guest performers included many bluegrass/Americana musicians and artists like Vince Gill, Sam Bush, Jim Lauderdale, Sierra Hull, Claire Lynch, Del McCoury, Ronnie McCoury, Robbie McCoury, Stuart Duncan, Rob Ickes, Trey Hensley, Molly Tuttle, Josh Williams, David Mayfield, Dale Ann Bradley, Darrell Scott, Missy Raines, Bryan McDowell, Todd Phillips, Buddy Spicher, Matt Combs, and Kenny Malone."
A track from the album, a cover of "I've Gotta Get a Message to You", won an International Bluegrass Music Award (IBMA) for Recorded Event of the Year. Additionally, the album was nominated for Best Bluegrass Album in the 60th Annual GRAMMY® Awards.
Osborne continues to actively perform with his band, the Rocky Top X-Press in 2018.
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