This article has multiple issues. Please help improve it or discuss these issues on the talk page. (Learn how and when to remove these template messages)(Learn how and when to remove this template message)
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 compliment 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.
- "Singing Like He Feels: A Conversation with Bobby Osborne". The Bluegrass Situation. 2017-07-14. Retrieved 2017-08-04.
- "Osborne Brothers - A high lead, a long run - Page 2 of 5". No Depression. 2000-03-01. Retrieved 2019-06-21.
- "Watch Alison Krauss Sing Pleading 'Windy City' on 'Jimmy Kimmel'". Rolling Stone. Retrieved 2017-08-04.
- "Alison Krauss Soars to No. 1 on Billboard's Country and Bluegrass Charts With "Windy City"". Nash Country Daily. 2017-02-28. Retrieved 2017-08-04.
- "At 85, Bluegrass Legend Bobby Osborne Looks Back on Appalachian Upbringing & His Legacy". Billboard. Retrieved 2017-08-04.
- "2017 International Bluegrass Music Awards - Bluegrass Today". Bluegrass Today. 2017-09-28. Retrieved 2018-01-30.
- "Bluegrass legend Bobby Osborne celebrates first solo Grammy nomination". The Tennessean. Retrieved 2018-01-30.