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Born and raised in rural Tennessee Mike Webb learned to play dobro and banjo from longtime Roy Acuff sideman Pete "Bashful Brother Oswald" Kirby. Mike Webb worked for a time in Grand Ole Opry member Wilma Lee Coopers band the Clinch Mountain Clan. He teamed up with another Acuff band member, Charlie Collins and worked as a duo for 11 years until Collins' death. Having played dobro on and off with the Tennessee Mafia Jug Band Webb then joined that group full time appearing on the Grand Ole Opry as well as across the country and abroad. He has appeared on the Marty Stuart Show on RFD with the group often performing comedy as well as playing dobro. Always willing to help a good cause he has been closely involved in his community often doing benefits to help the Senior Citizens Center as well as other worthy causes.