At around five years old, Gerald Edward "Eddie" Montgomery began performing with his parents' band, Harold Montgomery & Kentucky River Express. When Eddie reached his teens he joined his father's band full-time and replaced his mother, Carol, as the group's drummer.
As a teenager, Troy "T-Roy" Gentry began doing guest vocals with area bands and eventually landed a gig with a group in his hometown of Lexington, Kentucky.
Eddie Montgomery and Troy Gentry first played together in Early Tymz, a Lexington, Kentucky, band formed in 1990 and led by Montgomery's younger brother, John Michael Montgomery. After Early Tymz broke up, the Montgomery brothers and Gentry formed another band, Young Country, but both John Michael Montgomery and Troy Gentry both left soon afterwards to pursue solo careers.
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