In the early 1990s, he began playing in a number of bands with partner Eddie and Eddie's brother, John Michael Montgomery. After he failed to secure a solo record deal when he won a talent contest in 1994, he formed Montgomery Gentry in 1999.
In 2000, Montgomery Gentry won the title of Top New Vocal Duo from the Academy of Country Music.
After marrying Angie McClure in 1999, they gave birth to a daughter named Kaylee in 2002. He also has a daughter named Taylor from a previous marriage.