In 1990, the duo that would become Montgomery Gentry first took shape: That year, Eddie Montgomery formed a band with his brother, singer-songwriter John Michael Montgomery, and Troy Gentry. When John Michael Montgomery's career began taking off, Gentry tried first tried for a solo career ... but then, he and Eddie Montgomery reunited, and Montgomery Gentry was born.

Montgomery Gentry signed to Columbia Nashville in 1999. The duo released eight studio albums, three of which have been certified platinum. Among their biggest hits are "Something to Be Proud of," "Lucky Man" and "My Town." All together, Montgomery Gentry earned five No. 1 singles.

In 2000, Montgomery Gentry were named Top New Vocal Duo or Group at the ACM Awards and Vocal Duo of the Year at the CMA Awards. From 2001 through 2009, they were nominated for Top Vocal Duo at the ACM Awards and Vocal Duo of the Year at the CMA Awards each year, and in 2009, the duo was invited to join the Grand Ole Opry.

Flip through the photo gallery below to re-live some of Montgomery Gentry's biggest career milestones:

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