Troy Gentry’s heart was like how he lived: wide open, full-tilt, up for anything. He loved just about everybody, worked hard to make people happy and never met an adventure, honky-tonk, all-night party or hardcore hillbilly rocker he didn’t like.

When I met Montgomery Gentry—halfway past the launch of 1999’s Tattoos & Scars—it was because the circus had overwhelmed the music. With their hard-charging post-Southern rock dressed up as raucous barroom country, they were living the life, and had turned into a bit of a sideshow of booze, booze and more booze. Everybody wanted to drink with them, and they took all comers. But nobody was ever left standing. Into the debauchery and wild nights there something relentless and blue-collar. Somewhere between the sweaty factory men in Cleveland and Akron, Ohio clocking muscle-aching eight-hour shifts and Merle Haggard’s unblinking reality, they kept their dignity even as they swung hard and shot out the lights. It’s a kind of brio I didn’t understand ‘til I moved to Florida, and my father found the bars “west of Military Trail.”

Out there, South Florida paradigms fell away; they weren’t playing, but they were having fun. You took stuff outside. You worked up a sweat worse than the condensation on your Bud longneck in the airless bars. And you stood down to no one. You could plan on sidestepping two or three fights in the unpaved parking lot on a way to the best time you’d ever had—people were friendly, the band loud, the energy uplifting, all the way to closing.

Sitting on their manager’s desk, I had to explain the duo had pretty much shot their shot at critical mass. Credibility was not for them; but there was one thing. CMA Duo of the Year. The incredulity busted their faces. The pair who’d become the WWF in boots, brazen musicality and a bottomless bar tab, couldn’t believe the hubris.

“You mean the Brooks & Dunn Award?” Troy cracked, flashing that smile that was all gleam and a hint of dimple. His eyes flashed, too, titillated by the unthinkable.

“Yeah, the Brooks & Dunn Award,” I echoed.

They asked to step into the hall, taking the manager with them. They were gone almost long enough for me to regret sitting on that hard-edged desk. But they came back deadly serious.

“Let’s do this,” Troy said.

“Yeah,” Eddie Montgomery agreed. “Let’s do this.” In a world of John Prine and Rodney Crowell, Patty Loveless and Emmylou Harris, signing Montgomery Gentry made no sense. But a scrappy Cleveland girl saw the fighter’s glint and deep desire to tattoo something more than tire tracks on a Kentucky back road in their eye. Guys like them know how hard it can be. They don’t whine or flinch, and they’ll just keep coming.

When they took that stage, they played for keeps: guitars surging forward, the drummer sharp and pounding. It was merciless what they did to songs.

And God liked these two. Backstage at the American Music Awards, chewing my cuticles with John Dorris, Jr., their manager, I saw them named Best New Country Act. It was a total left-field win. Suddenly we knew: we were in the game. As I dragged them through the press rooms and standup one-on-one interviews—Eddie heh-heh-heh-ing, Troy gleaming and winking—they were a hot knife through butter.

As we stopped at a late-night quickstop in a limo half a block long in the worst part of town on our way back to the hotel from Los Angeles’ Shrine Auditorium, three black ladies—quite possibly professionals—gave Montgomery the eye. Gentry just cackled, smirking. “He’s a big man in a bigger hat; the ladies just love him.” He burst out laughing when his partner opened the car door to climb inside, fresh pack of smokes shook to the top and ready for lighting.

Not long after that, we took the boys to the Palm for Sunday dinner with Chuck LaBella, who’d booked Politically Incorrect, now handling music for Craig Kilborn. Who would be more willing to take a chance on an act out of the box? Who’d get the relentless gauntlet that comes from living the Southern rock dream?

They came in full drag: Eddie in a full-length black duster and the BAH (Big Ass Hat), Troy in a close-cut buckskin jacket, like they wore to the Troubadour in its heyday. In a room packed with the likes of Russell Crowe, Gina Gershon and Rick James, every eye was on them.

This was larger-than-life in real life, not characters projected on a giant screen. My best friend, who happened to be in California, never got over it. “There were all these huge movie stars, and they were invisible.”

Part of it was how they looked and dressed, no doubt. But part of it was their raw charisma. They exuded it. Troy, especially, who seemed to fill his tanks on feeding women’s sense of self. The more he laid it on—going nowhere, he loved his wife Angie, who looked like a cross between a Bettie Page vixen and a little fox—the more they ate it up, and the happier it made him. When they won that AMA, given people had written them off as ignorant rednecks, I thought, “Queen Latifah.” We could not get them on TV, given the resistance to the roughneck drive of their sound. What would be more radical for the pair? Running it by them, they both puffed up.

“Hell, Yeah!” they chimed. They loved the idea of a talk show built around a founding hip-hop queen.

So, they went to New York, played “Hillbilly Shoes” for an urban TV audience fielded for the pioneering female rapper. They turned the place out. Up. Side. Down. Screeching, catcalling, the works. The song that invoked the delivery of Christ in its opening lines and drilled down to how we view, marginalize and thrust people into the worst possible interpretations.

“You want to judge me,” Gentry’s tenor leveled, true and strong, “for the whiskey on my breath… You think you know me, but you ain’t seen nothing yet.”

It pierced, went straight in like a hollow-point bullet. Tough, staunch, but mostly knowing what those words meant. It wasn’t a threat, wasn’t a taunt. But it was a menace to the truth that didn’t need explaining, and it was a truth they were more than willing to stand up for.

By the time they got to the bridge—"Work all day in the muck and the mire/ Dance a little jig and a stomp by the fire/ Ain’t too much these boots can’t do/ Might even kick a little sense into you”—and Montgomery’s near-clogging in very large red cowboy boots, the crowd was wild. It was a giant throwdown in an ice-cold Manhattan TV studio.

In the hotel bar after, waiting for a car to the airport, Troy, who’d always found me a little too Type A and preppy, taunted me just a little. Why wouldn’t I ever drink with them? Not even one? Couldn’t I take it? What was I scared of?  You don’t say, “Watching you two, someone has to stay sober.”

When I final relented, he was beyond a gentleman. Having the bartender ice the tequila down, putting it in a straight rocks glass, he made sure there were plenty of lime for the post shot.

Clinking glasses, we threw it back. Glasses coming straight down, he was shocked I didn’t flinch, didn’t gag or squeal.

“You can do that,” he said incredulous.

“I’ve been in bars since I was 13,” I explained. “I have no need to keep up with you. I can’t win, and I prove nothing.”

He laughed so long, the barmaid came over. Robin Majors, their long-suffering tour manager, did, too. “What do we have here?” implied by the body language. We all just laughed more without saying a word, as much at the surprise inside the obvious as the buoyancy of laughing.

They weren’t fancy, and they weren’t interested in the affectations that consumed so many new acts. Working-class people were their stock in trade; they applied the same ethos to how they chased their music. Not that they didn’t have fun—giant, oversized barrels of fun, which they often tapped for everyone and anyone around. Buy a ticket to the show, and know: They were coming for ya. Throw down, drink up, laugh out loud and enjoy every last moment, because Monday is coming.

Watching one of his opening acts of the 21st century, new-country slant, Kenny Chesney half-smiled, looked sideways and said, “Man, I miss having Eddie and Troy out here! They got the audience so worked up, you got on that stage and they were just ready to get rocked.”

Beyond the drinking, there was a code of honor between them. When the stories out of being so wasted at Country Radio Seminar and almost pulverizing CBS exec Jack Sussman made their way back to me, Gentry got a solid verbal beating all day long. I’d been furious at them for showing their ass with a man who in many ways controlled access to network award shows, but it wasn’t until we were in the room waiting on the ACM Awards nominations that I realized it was Montgomery who’d been falling-down drunk.

“You didn’t tell me,” I chided. “You didn’t say anything.”

“You didn’t ask,” he hissed right back. “You rode my ass all day, sure it was me… See, smarty-pants.”

Fed up or not, he knew it was my fire to see them succeed that drove me. It was that faith when so many people thought they were a train wreck in a Silver Eagle tour bus that bound them to me, unlikely a team as we were.

Acts you can believe in like that, who look at those regular fans and see heroes, who want to lift the average up high, say “Hell, Yeah,” empower and encourage, the ones who almost incinerate you with how much they mean it. That was Montgomery Gentry on their best days.

Like Huck Finn or Ferris Bueller, he was going to stretch the rules ’til they sprang back, snapped and flung across the room.

They’d surprise you, too. Robin Majors remembers the day they got their first tour jackets, how proud they all were, and drinking down on Lower Broadway like they did. Wandering out of the bar at closing time, they came upon a homeless man with in a t-shirt with no sleeves, shivering as the winter was starting to fall. Troy paused a beat, then he peeled off his coat, and handed it to the dirty man who’d been on the streets too long. They didn’t have the money to just get another, and proud as Troy was of that tour jacket, he saw the need—and he’d rather do the right thing.

That was the deal: They’d do whatever was required. Seen, unseen, it didn’t matter. Get a tattoo for CNN? Sure, if it could be at Sunset Tattoo where the Allmans, the bikers and hard rockers got inked. Troy talked through the whole thing, filling out his bad-boy bona fides without a single declaration. Flying cross-country when necessary, waking up before daylight—or not ever bothering to sleep—to do morning television. Meeting and greeting ‘til it was a blur of faces, places, broken white lines and tires turning.

They understood the conventional approach of good reviews, building critical consensus and meaningful TV wasn’t going to happen, given the way Tattoos & Scars launched. It was going to be a different tack: powerhouse momentum and the larger-than-life personalities were what was going to deliver. Because who they were was in the music.

When they took that stage, they played for keeps: guitars surging forward, the drummer sharp and pounding. It was merciless what they did to songs. But when you come up in bars where you either get tipped or dodge beer bottles, you learn how to stand and deliver. You learn about Saturday nights that are life or death, people who need to blow off steam, who dig in and make life happen there at the margins.

In their life-by-the-horns ethos, they burned down an abandoned house to demonstrate the intensity of their emotions for their “Lonely & Gone” video, provided an FFA Scholarship when nobody in Nashville was thinking about family farmers. They weren’t afraid of press releases about stolen tube socks and jockey shorts, or the catfight between Miss Easy Rider and the Penthouse Pet of the Year over the privilege of bringing them on at the Sturgis.

They played the Midnight Jam at Ernest Tubb’s record store, honoring a tradition that goes back to when the Opry was at the Ryman. They played Tootsie’s, because scrappy bar bands with no shot at the brass ring know that’s as close as they’ll ever get to the dream of making it in Nashville. And when they finally made their Opry debut, Eddie and Troy couldn’t help talking about how much it would’ve meant to Eddie’s honky-tonk-singing father.

It was cumulative. Piece by piece, moment by moment.

Suddenly, people were talking. They were laughing, but not at them. Montgomery Gentry made country music fun. And real. It was the same kind of stuff Haggard, Cash, Jones and Coe had done before them: Raise hell, and live to tell about it. And Charlie Daniels, whose “All Night Long” they’d cut on their gold and heading-to-platinum debut, adored the wild-eyed singers.

To see Troy Gentry doing Gregg Allman’s “Good Clean Fun,” perhaps the least subtle come on ever written, was to watch someone soaking in a song’s ultimate possibilities. Naughty was as naughty did, but when Gentry pushed the notes, lingered a bit as he made his way across the stage, it was obvious there was little clean or church-leaning about his intentions. Like a bad kid who knew how to charm, he shamelessly churned the song, knowing full well there was no nuance, and not really caring.

Going into the CMA nominations, all they needed was to make the final five. If they did that, we had Charlie Daniels in our pocket—and a whole other tilt to the smoothed-over country that was Nashville at the century’s turn. And if they did that, well, hell, that promise made in their manager’s office of “I can’t turn the press around, but there is one thing: CMA Duo of the Year” was almost half-true right there.

This performance—and moment—wasn’t just for two kids from Lexington, Kentucky; they were playing it for every loser, shattered vet, broken housewife and outsider.

Funny thing about real-deal country boys: they just keep swinging. With the nominations announced, producer Walter Miller, a man who saw the comic genius in Sam Kinison, got why and how they’d shake up his show, understood the energy they’d inject—and how they’d break up all that serious artistry with a good old-fashioned throwdown. And before there were Grammy moments, they were bringing something unique by pairing with Daniels to perform the icon’s party anthem at the Grand Ole Opry for the live telecast.

When the night came, they were just nervous enough. They were also just mad enough at the people who’d written them off, and serious enough about every also-ran whose dream they were also carrying on their backs. This performance—and moment—wasn’t just for two kids from Lexington, Kentucky; they were playing it for every loser, shattered vet, broken housewife and outsider.

When they finished, Vince Gill came from the wings, twirling and jabbing his mic. Laughing, he announced, “I think I’ve got a new trick…” as the cheers finally receded. The normally staid crowd had been on their feet, rocking. Maybe Montgomery Gentry weren’t refined, but that was never the core of country music.

A few moments later, the camera cut to the duo standing in the wings, hearing their names called as nominees for an award that had previously been a foregone conclusion. The tension tightening their faces, but it couldn’t blunt the desire blazing in their eyes. They almost weren’t breathing as the envelope was opened, the card withdrawn.

When they heard their names, there was a freeze-frame moment.

Eddie jumped on Troy, hat flying. Jumble, tumble, jumping up and down, clearly consumed by the moment.

They walked onto the Opryhouse stage, clearly moved, absolutely shaken, completely proud. With tears in his voice, Troy thanked me in two pieces, first name torn from the last. He knew how much I believed, and how much I knew what their music could mean. He thanked the label, the managers, country radio, especially the fans. 10 months earlier, this was an impossible dream. They’d done the unthinkable, never considered it could happen, but just kept swinging.

Sometimes someone else’s faith is even more important that your own. After all of it, the two screw-ups from Lexington were now the CMA Duo of the Year, breaking Brooks & Dunn’s eight-year stranglehold on the prize. They had given their hearts over to chasing the music, playing for the fans. And no matter what happened, they never wavered. It’s harder thank you think.

Two days later, I was fired. The label didn’t like how much gratitude I got, and so I had to go. Brooks & Dunn scooped me up, and then, suddenly, Montgomery Gentry was on B&D’s Neon Circus, which was Lollapalooza with spurs.

If country had gone metrosexual—and Gentry’s ridiculous good looks didn’t fly in the face of that—they remained full-grown men in full possession of their brio. When USA Today wrote a profile of Brooks & Dunn, anchoring on the tour, they headlined it: “The Return of Macho Country.” It was a wild summer.

Funny thing about real-deal country boys:
they just keep swinging.

Through it all, the duo never ever thought twice about shunning the political refugee. Fired for politics, but friend for passion. It was simple like that. Troy would find me in catering, wink across the soundboard, stop in the parking lot and talk about nothing; Eddie would do the same. They had the line on the best moonshine that tour, so they were ridiculously popular.

Eventually, they came back. Eventually, it was time again for them to move on as clients. It’s the nature and flow of the music business. New teams, alliances, needs. New priorities, notions, ideas. Not everybody gets the fundamentals, nor do they realize it’s the music that matters. Most artists never look back; some barely remember. But whenever you’d run into them on the road, it was always fun, always family.

Riding in the bus into shows, girls flashing, there’s nothing like a South Florida crowd “west of Military Trail” to really understand. At the same time, Troy taking one of my Palm Beach girlfriends riding around the chili cook-off parking lots on his Harley, he made the out-of-place seem natural. Teasing Binny about being on the back of his hog, they drove off laughing. Laughing came natural to him.

It wasn’t that life just beaded up and off him, either, but more how determined he was to be in love with life, his wife, his daughters and everyone in his purview. He was going to live every moment, taste every possible experience there was. Like Huck Finn or Ferris Bueller, he was going to stretch the rules ’til they sprang back, snapped and flung across the room.

The thing about living these gypsy lives, you never know when or where you’re gonna cross paths. It’s always somewhere out there, and just Sunday, in Miami for an all-day festival, there they were. Larger than life, they were standing against a backdrop where they posed for pictures and talked up the people who were backstage. They were in their glory.

Few people do meet-n-greets with such joy. Lingering behind an equipment case, I smiled, remembering how much every fan truly mattered to them. Leaning in for pictures, looking into eyes when they spoke. Yes, he had a million-dollar smile, but he also meant every penny of it. Watching an act meet their people is always fun, seeing the unadulterated spark on people’s faces.

As someone who’s learned to live in the cracks, mostly invisible even in blinding pink and green, I was surprised to hear Eddie in that gruff, husky voice go, “WHAT are you DOING here?”

The small talk back-and-forth about health and kids, life and how it’s going ensued. Eddie got pulled away, and Troy repeated the pattern.

“You good?”

“Of course.”

“Getting in any trouble?”


“That’s no fun.”

We both laughed; I explained about the book I’d edited, Woman Walk The Line, a collection of essays by women writers about the female country artists who changed their life. “You probably wouldn’t read it,” I ventured. “You don’t know that,” he volleyed.

As much as he liked women, he just might have. “Tell me more when we come back. Okay?”

Then they were gone on a golf cart to change, and get ready. Middle of the afternoon on blacktop is a tough time to play in South Florida. They didn’t care.

From the moment they emerged from the wings, Troy was on that stage, guitars blazing, trading vocals with Eddie—and they made it feel like the biggest party in a city that knows how to party. Hot and sweltering as it was, the crowd was up, dancing, yowling and throwing down to “Hillbilly Shoes,” “Gone” and Charlie Daniels’ “All Night Long.”

No doubt when Troy got in the helicopter to go flying, it was all the fun and adventure that made him go, “Hell, yes! I’m in…”

When Southern rock lost its cache, Eddie and Troy realized that was the music of their culture: the working people, the deep South, folks who liked the guitars to have that tinge of burn, the drums to crash and the words to dig into the moment and lift people up.

And that was the thing about Troy, it was all in such good spirits. It always rocked, and it made people feel more dangerous than they were, yet somehow kept them safe as new kittens. To be able to walk that line, maybe it truly does take hillbilly shoes.

All I know is they were having fun, throwing down. No doubt when Troy got in the helicopter to go flying, it was all the fun and adventure that made him go, “Hell, yes! I’m in…”

Who knows what went wrong? Maybe it doesn’t matter. Maybe it’s okay not to know, because it won’t change anything. Unlike Stevie Ray Vaughan, who died in a helicopter crash out of a gig, this was something undertaken for the thrill—and I can only hope that there was that rush before everything went so wrong.

50 is way too young. Especially for someone so strong, so in shape, with his eyes still firmly on the prize. For a band that had moved beyond merely tracking the charts and waiting on the awards nominations, they were kicking up the tar and dust, pushing the music like only a bar-honed band truly can.

It’s late afternoon, and I’m having a prickly-pear margarita; the salt comes from the tears I can’t quite keep in my eyes. It’s been years since they toured with Kenny Chesney, a constant presence out on the road, and years and years since we’d all worked together. But somehow all those memories rush in, vivid as Technicolor.

Turning around to think about small talk in the sticky heat last weekend, and a picture someone stole of me being busted by my friends at the back end of their meet-n-greet, I have a lump in my throat.

But more than that, it makes me realize: You better get out there and do it. Tell people you care, remember what really matters. Have the fun, feel the freedom, embrace the exhilaration; Troy Gentry sure did – and he’d expect no less from the rest of us.



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