The duo’s first single, “Hillbilly Shoes” hit the Billboard Country charts in February 1999, peaking at No. 13 on the Hot Country Songs chart. Their next release, “Lonely and Gone,” would become their first of sixteen top 10 Hot Country Songs hits, peaking at No. 5. It would be two years until they hit the top 10 of the charts again, as “She Couldn’t Change Me” would make it all the way to the runner-up position on the charts in July of 2001. Still, their star was on the rise. In 2000, they unseated Brooks and Dunn as winners of the CMA’s Vocal Duo of the Year award, and watched as their first nine studio albums all hit the top 10 on the Top Country Albums chart – through 2011’s Rebels On The Run.
2002’s “My Town” proved to be the song that cemented their fortunes with country radio. The track made it all the way to No. 5 on the Country Airplay chart, and every subsequent release through 2011 made it to the top 25 on the list. Their first Country Airplay No. 1 hit came in 2004 with “Something To Be Proud Of,” topping the chart four additional times after that, most recently with 2008’s “Roll With Me.” Gentry’s voice can be heard most prominently singing lead on the 2003 single “Hell Yeah,” which peaked at No. 4 on Hot Country Songs.
All in all, the duo placed twenty-eight songs on the Hot Country Songs list, with sixteen becoming top 10 hits. The duo has sold over six million albums in the U.S. through Aug. 31, 2017, according to Nielsen Music, with their best-selling album being 2002’s My Town, which has sold 1 million copies. They earned two Gold and two Platinum albums during their career. Moreover, their music has moved 6.4 million song downloads and collected 163.1 million on-demand streams in the U.S. Following their consistent success, the duo achieved a career goal in 2009 with an invitation to join the cast of the Grand Ole Opry from longtime hero Charlie Daniels.
In 2014, Gentry spoke to Billboard about getting to fufill some of their longtime dreams by performing with their heroes, like Daniels: "When we started, Charlie Daniels came in and recorded 'All Night Long' with us. We were on Never Say Die, Waylon Jennings' last album, performing with him. On the road, we've worked with Hank Williams, Jr., Kris Kristofferson, and Merle Haggard. We've paid tribute to icons like George Jones, Lynyrd Skynyrd, and Glen Campbell."
And in 2015, Gentry told Billboard how much he and Montgomery enjoyed performing for their legion of fans. "Eddie and I are road dogs. We love traveling and playing live. We try to stay as busy as we can, and thanks to all the folks at CAA, they do a real good job at keeping us working."
The duo left Columbia Records in 2010, and signed with Colt Ford’s Average Joe’s Entertainment, where they scored a top 10 hit with “Where I Come From” in 2012. They switched labels again in 2015, recording the album Folks Like Us for Blaster, which peaked at No. 13 on the Top Country Albums chart. At the time of Gentry’s passing, the duo were putting the final touches on a new album for Average Joe’s, whom they had re-signed with – planned for 2018.
Gentry married Angie McClure in 1999, and had two daughters – Taylor, from a previous marriage, and Kaylee, born in 2002. Our thoughts are with Gentry's loved ones during this difficult time.