Both proud Kentucky natives, Gentry and Montgomery's first joint musical effort was as part of a band called Young Country. After two years with that band, Gentry left to try his hand at a solo career. He won the Jim Beam National Talent Contest in 1994 and earned opening slots for Patty Loveless, Tracy Byrd and John Michael Montgomery (who is Eddie’s younger brother).

Without being able to turn up a solo deal, Gentry forged a duo with Montgomery, building on their rowdy fan base in the Kentucky nightclubs. Their onstage experience has established them as a good-timing crowd favorite, while they’ve scored country hits like “Lonely and Gone,” “She Couldn’t Change Me” and “My Town.” They won the CMA vocal duo award in 2000.

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