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, Montgomery Gentry were nominated for Top Vocal Duo at the ACM Awards and Vocal Duo of the Year at the CMA Awards each year. In 2009, Montgomery Gentry were invited to join the Grand Ole Opry.

Montgomery Gentry last released an album, Folks Like Us, in 2015. On Friday (Sept. 8), the duo was scheduled to play a concert in Medford, N.J.; sadly, prior to the show, Gentry was killed in a helicopter crash.

"It is with great sadness that we confirm that Troy Gentry, half of the popular country duo, Montgomery Gentry, was tragically killed in a helicopter crash," a press release from the duo's record label, Average Joes Entertainment, sent out on Friday afternoon, reads. "Details of the crash are unknown. Troy Gentry's family wishes to acknowledge all of the kind thoughts and prayers, and asks for privacy at this time."

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

Country Artists Remember Troy Gentry