- In 2001 won the Grammy for "Best Male Country Vocal Performance" for his a capella rendition of the traditional song "O Death", from the soundtrack to O Brother, Where Art Thou? (2000).
- Received an honorary doctorate in music from Lincoln Memorial University in 1976.
- He was awarded the 2006 American National Medal of the Arts by the National Endowment of the Arts in Washington D.C. for his services to music.
- Inducted into the Grand Old Opry in January 2000.
- With brother Carter Stanley (d. 1966) formed the much-heralded bluegrass band The Stanley Brothers.
- Carter played guitar, and the two brothers performed at school and community gatherings, inspired by musicians they heard on the radio. In 1946, they formed the Clinch Mountain Boys, named after a mountain ridge in the region. They played on radio stations in southwestern Virginia. They were soon popular with audiences and began making records.
- He was born into a large family - his older brother Carter, plus seven older step-siblings. Both parents had been previously widowed. His mother bought him his first banjo for five dollars.
- Synonymous with Appalachian music, Stanley experienced a resurgence with his contributions to the 'O Brother, Where Art Thou' soundtrack.
- Named a "Living Legend" by the United States Library of Congress in April 2000.
- In 1985 received the United States National Endowment for the Humanities' "Traditional American Music Award". He was the first to receive this award.
- In early January 2007 Stanley was hospitalized with pneumonia. By mid-January he was back out on tour.
- Coeburn, Virginia (September 2006)
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