The banjo picker started his career with the Clinch Mountain boys and have shaped the sound of bluegrass to what it is today. Some of Stanley's best known work came in 2000 with his contribution to the "O Brother, Where Art Thou?" film soundtrack where he sang on the Appalachian dirge, "O Death". It was that song which gave Stanley a Grammy award in 2002 in the category of Best Male Country Vocal Performance, one of his three Grammy wins in the past 11 years.
The farewell tour, which starts on October 16 will run through December 2014, and will be Stanley's last.