First Bluegrass Group to Play a College at Antioch College in Yellow Springs, Ohio (Osborne Brothers): 1960
Member of the Grand Ole Opry since Aug. 8, 1964
Original Recording of Rocky Top Released as B Side to My Favorite Memory (Osborne Brothers): Dec. 25, 1967
CMA Vocal Group of the Year (Osborne Brothers): Oct. 10, 1971 
6 CMA Vocal Group of the Year Nominations (Osborne Brothers): 1970-1975
Music City News “Number One Bluegrass Group” (Osborne Brothers): 1971-1978
First Bluegrass Group to Perform at The White House (Osborne Brothers): Mar. 17, 1973
Rocky Top Made an Official State Song of Tennessee (Osborne Brothers): Feb. 15, 1982
Inducted into the SPBGMA Preservation Hall of Greats: 1986 
SPBGMA Male Vocalist of the Year: 1990
“Kentucky” Made an Official State Song of Kentucky (Osborne Brothers) Feb., 1992
Inducted into the International Bluegrass Hall of Fame (Osborne Brothers): Sept. 22, 1994
IBMA Instrumental Album of the Year (Bluegrass Mandolin Extravaganza): Oct. 19, 2000
IBMA Recorded Event of the Year (Bluegrass Mandolin Extravaganza): Oct. 19, 2000
Inducted into the Kentucky Music Hall of Fame: 2002 
Kentucky Star Award: 2004
Uncle Dave Macon Days “Heritage Award”: Jun. 12, 2008
Inducted into the International Bluegrass Hall of Fame (Lonesome Pine Fiddlers): Oct. 1, 2009 (Bobby is the only person to be inducted to the IBMA Hall of Fame twice!)
Great !! Love this !!
I worked with Wynn Osborne 1977-1980 cut a album 1980 5 string magic on cmh records with Wynn this is one of the most talented family s I’ve ever been around sonny and Wynn are great banjo players bobby has always one of best singers in bluegrass Robby is good picker and patsy wynn s mother good singer and songwriter. Awesome talent Osborne brothers was my all time favorite band now my cousin Gary reece great banjo player is working with bobby. Wynn is my favorite banjo player they all are great glad to know this group great folks too.