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Troy Gentry Proved Nice Guys Can Finish First

One word kept popping up again and again on Twitter Friday afternoon (Sept. 8) as the country music community learned of Montgomery Gentry singer Troy Gentry’s death: friend.

The emotional depth to the standard round of tweets from contemporaries and legends was beyond standard. Gentry’s death at the age of 50 is not the same as when an elder statesman like Merle Haggard dies — very few of today’s top stars interacted with the Hag much, and while he surely influenced younger generations, he wasn’t a friend to many under 40.

That’s not true for Gentry. Blake Shelton, Rhett Akins, Lee Brice, Gretchen Wilson, Terri Clark, Travis Tritt, Brad Paisley, Chris Young, Cowboy Troy, Jake Owen … it’s a seemingly infinite list of singers from the Montgomery Gentry generation and beyond that were personally devastated. Who knew country-rock outlaw Shooter Jennings was such good friends with Gentry?

As a duo, Montgomery Gentry overachieved. That’s not a slight; the opposite, after all, is to underachieve, and who wants to be known as an underachiever? Hard work and kindness filled any holes in their artistry. Perhaps only the top 10 percent of country musicians can get by on talent alone.

For years they played runner-up to Brooks & Dunn at awards shows, but they were just as reliable. Troy Gentry the singer was no Ronnie Dunn, but the duo’s best songs impacted their fans in the same way as Dunn’s most moving ballads. “Something to Be Proud Of” was capable of providing all the feels in the same way as “Believe” — theirs was a more blue-collar, rugged brand of country and rock that took time to be celebrated on a commercial level.

For three years Montgomery Gentry’s track record with radio was spotty. Two Top 5 singles (“Lonely and Gone” and “She Couldn’t Change Me”) fell amongst a few that barely dented the Top 40. By 1999 the duo had been together nearly a decade, building a loyal fan base the old fashioned way, one fan (or friend, as the duo was fond of saying) at a time. They weren’t good live, they were great. Eddie Montgomery’s stomping stage antics were the show, while Gentry’s stability provided the go. He was the glue, often taking lead in interviews to allow his partner to do what he did best: interject with a signature punchline, rowdy outburst or baritone laugh. Montgomery Gentry made great radio.

As a list of Montgomery Gentry’s Top 10 songs shows, from 2002 to 2008 MoGent owned the world until their grip on radio started to loosen. After departing Sony something remarkable happened: they got a second chance, and then a third and a fourth. Rebels on the Run produced a Top 10 hit for Average Joes Entertainment. For the next record, they’d hop to Blaster Records before coming back to Average Joes to finish an album just prior to Gentry’s Sept. 8 death in a helicopter crash.

This doesn’t happen to an ass. When a decision maker is tasked with dropping an artist after a series of poor-performing singles on the radio or signing an artist to a new record deal, potential is considered, but a tie can go to the nicest guy in the room. Who does a label want to work with? Who does a label president believe will do the work necessary? Again and again, people took a chance on a pair of aging country-rockers with some baggage (the ugly bear incident haunted Gentry to the end of his days).

The Country Community Grieves Over the Loss of Troy Gentry

This isn’t the rule. Any artist (or journalist) could list artist after artist that was prickly, difficult, rude or a flat-out jerk. Reputations can open a door or slam one shut — when you ask why no one will sign your favorite artist, or why no one is playing your favorite artist on the radio any longer, consider the possibility that nobody likes him or her.

But everyone liked Gentry and Montgomery. They were easy to cheer for to the tune of 15 Top 10 hits and a 2000 CMA Vocal Duo of the Year win. To his final day, Gentry was doing the work necessary to better his band’s chances moving forward. They certainly didn’t have to do the free charity shows or the interviews. Montgomery was besieged by personal troubles including cancer, divorce, bankruptcy and the death of his son. Gentry himself lost a brother too soon and helped his wife Angie through cancer. He carried it all on his broad shoulders and continued to show up on time and answer sometimes difficult questions with poise and grace.

One final note about Gentry’s unbiased kindness comes from a fan. @Shann77 on Instagram shared a story with Taste of Country that shows the Kentucky native’s manners weren’t reserved for the cameras (see below). The genre lost two gentle giants on Friday (Don Williams also died). In both cases, their big hearts will be missed long after their musical influences wane.

November of 2006…one of the coldest November days in Corinth, MS that I can recall….I was at my THIRD job for the holiday season and had been up since 4:30 AM that morning… I was not very familiar with country music and I think that's why they gave me the job of being a Runner (which is just a credentialed gopher) for Montgomery Gentry and Little Big Town. I remember being invited onto MG's tour bus to meet Troy Gentry. He then proceeded to tell me he wanted to have a cookout. I'm pretty sure I had a confused look on my face, wondering if I had heard him correctly….I mean, you could see your breathe the minute you walked outside, but yes, he wanted to have a cookout and gave me a specific list of items he needed. I went all over the big town of Corinth trying to find his specific ketchup and mustard bottles..( thank you Dollar Tree!) After dropping Little Big Town back to their hotel, I was throughly exhausted when someone on their team told me I could go lay down in this little room behind the stage to rest for a few hours before my next errand. It was cozy, quiet (besides the audience noise) and dark. I was just about to drift away when I heard the door open, my face was turned to the inside of the couch so I figured whomever it was would just leave…Nope! I listened to a man quietly change his clothes, while humming to himself, as I pretended to be fully asleep. He stayed in there for what felt like forever, until I heard a knock on the door and someone say "stage call, Troy"… I have had quite a few crazy adventures in my life along those lines, but that is one of the most vivid….#troygentry #montgomerygentry #rip #hineshouse #nashvilleliving

A post shared by shanann77 (@shanann77) on

Next: Troy Gentry, In Memoriam

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