Dean began his music career at age five, learning to play the piano from his father. While attending a concert by his cousins the Osborne Brothers, Dean fell in love with Bluegrass music. At age fourteen he got his first banjo, a Hondo II. In 1980, Dean graduated from his Hondo II to a 1979 Gibson Mastertone and formed his first band, the “Thousandsticks Express”. The band, named after Dean’s family home place in Leslie County, Kentucky, played until 1986, when the first version of the “Eastbound Band” was formed. During the 1990’s, Dean played a Rich and Taylor “Sonny Osborne” model banjo (#95122). He now plays a limitededition Osborne Chief, number 41, which was custom made by Frank Neat.
About the time that the “Eastbound Band” was formed, Dean began promoting shows in the Lexington, Kentucky area. In 1990 he started what is now known as “The Red Mule Bluegrass Festival”. In 1994 he started the Osborne Brothers Hometown Festival in Hyden, Kentucky to celebrate the career and contribution of the Osborne Brothers to Bluegrass music. The Osborne Brothers Hometown Festival was nominated for the IBMA Festival of the year in 2001. Also in 2001, Dean founded the J.D. Crowe and the New South Bluegrass Festival in Wilmore, Kentucky.
Dean has shared the stage with some of the most well-known names in the Bluegrass world, including the Osborne Brothers, J.D. Crowe and Ralph Stanley. He has also recorded as a guest artist with Richard Bennett and appears on Rebel Records first “Live” video featuring Richard and Wanda Bennett, Randall Barnes and Phil Leadbetter.
Dean has an album entitled “Kentucky Son”, which was released in 2000 by Pinecastle Records. He is now preparing, along with the other members of the band, to tour and record in 2003.
In his spare time, Dean enjoys training Tennessee Walking Horses, collecting antiques, instruments, vinyl records and bluegrass memorabilia.
He also spends time restoring an 1893 house in downtown Lexington, Kentucky.