Cover Story: So my brother wants to be a country-music star

The first thing you need to know about my little brother is that he never does anything on a small scale.</
Take the Great Peach Campaign, for example, which really started the whole phenomenon of Bill Gentry: the biggest country-music star you’ve never heard of.</
In 2001, Bill was still honing his chops as a performer and gigging in little country-music juke joints. But he was also hustling enough to get himself a showcase in Nashville. Now, any aspiring country singer can book a “showcase” in Nashville. The trouble is, if no one knows who you are, no one is going to show up to see your show.</
For Bill Gentry, a Nashville showcase in front of an empty house was not an option. Hence the Great Peach Campaign.</
It began one morning when every single person who arrived to work on Music Row saw the same thing plastered on almost every bus-stop bench they passed: a sign that read, “Do You Know Bill Gentry?”</
A few weeks later, a second sign mysteriously appeared on almost every bus-stop bench around Music Row, this time with: “Have You Heard Bill Gentry?”</
This is where the peaches come in.</
The logic was simple. He is from Georgia. Georgia means peaches. So he buys 3,000 pounds of peaches. He buys 10 big wooden crates. He puts 300 pounds of peaches into each crate, along with a supply of baskets. Then he gets a couple of fake delivery company uniforms and enlists his old college roommate to help him. And then Bill Gentry delivers a crate of peaches – courtesy of Bill Gentry – to every major record label on Music Row. Individual peach baskets included.</
My kid brother had materialized in Nashville out of thin air and created an almost unheard-of buzz. Almost 1,000 people turned out at his showcase, including representatives from three record labels. One of them, the president of Virgin Records’ country division, called Bill’s publicist the very next morning to request a meeting. And even though the label closed its country division a couple months later, Bill Gentry had put himself on the Music City map.</
When Bill first announced his intention 10 years ago to become the Next Big Thing in country music, I watched with detached bemusement. I was a musician. I played blues music, the real stuff. To me, he seemed determined to market and self-promote his way to stardom. He struck me as a poor man’s Garth Brooks.</
I didn’t think he stood a chance.</
This was before he built a mammoth fan base in North Georgia; before he opened Wild Bill’s, the largest country-music club in America; before I saw him repel down from the roof to the stage to open a concert in front of 5,000 adoring fans; and long before the most powerful attorney in the music business decided he was going to get Bill Gentry a major-label deal.</
This month, he returns to Nashville to work with a big-name producer. He’ll record songs that will soon be on the desks of the top music executives in Nashville. And they will be pushed very hard by some very important people to sign him to a record deal. After all this time, my little brother is actually on the brink of becoming a country-music star. So, OK. Maybe I was a little wrong. But I’d thought he was merely chasing a dream.</
I had no idea he was actually trying to chase down a ghost.</
THE GREAT CAKE CAPER is truly the stuff of family lore. The cake in question was baked on a Saturday for a Sunday get-together. Bill and his older sister, Mimi, begged for a slice, but the cake had to remain pristine and uncut. Which brings up the second thing you need to know about my brother: Once he sets his mind to something, he’s not going to stop until he gets it. He’s the kind of person who thinks sheer force of his nature can transcend logic.</
After everyone went to bed, Mimi and Bill sneaked downstairs. They took a knife, cut all the way through the cake about a quarter inch from the bottom. Then they carefully lifted the cake from its bottom layer and placed it onto a new plate, and gleefully gulped down their bounty, thinking no one would be the wiser. Of course, they got busted. Bill always got busted. That was part of his charm.</
Bill and Mimi are actually my step-siblings. My father married their mother in 1979, 10 years after their father had died from heart problems. Bill’s father was Lee Gentry, a Presbyterian minister from Mississippi. Mimi and Bill were born in Mississippi but raised on a 250-acre cattle farm outside Carrollton, about 45 miles west of Atlanta. Their three oldest siblings were from their mother’s first marriage, to a former football star who also died unexpectedly.</
Creative juices flowed in the family. Lyle Garrett, the oldest brother, sang on Broadway and starred in European productions of The Phantom of the Opera. Mimi starred in musicals at the Springer Theatre in Columbus and modeled in Paris. Bill, the youngest, played the guitar and sang, but his ambition outstripped his natural talent.</
Bill, now 40, was always different from the other kids in the family. He was the problem child, clearly affected by the death of his father. “Bill was only 2 when that happened,” Mimi told me. “He spent many of his waking hours as a kid trying to find his daddy.”</
When he was 19, Bill dug one of his father’s old suits out of mothballs. He parted his hair like his dad, and had his mother take a picture of him wearing the suit and holding his father’s Bible. “He wanted to be like him,” says Mimi. “And everyone who knew our father says Bill is just like his daddy.”</
Another thing about Bill: Once he’d become obsessed with something, there was no stopping him – until the next thing came along. There was the bodybuilding phase in high school. The rock ‘n’ roll phase. The political phase in college when he interned for U.S. Sen. Sam Nunn and ran (unsuccessfully) for the Waleska City Council. And then there was the make-a-lot-of-money phase after he graduated from Georgia State.</
But those were nothing until Bill latched onto his greatest and longest-lasting obsession of all: the become-a-country-music-star phase.</
THE NEXT THING you need to know about my brother is that he is always late. To give you an idea of how bad he is, a few weeks ago we were meeting at 8 o’clock to go to a show, and he called at 7:45 to “warn me” that he was actually going to be on time.</
So I’m not surprised on the night I’m supposed to interview him that I’m standing alone inside the vast expanse of Wild Bill’s – the huge country-music club he built in Duluth – and he’s just texted me that he’s running late. The first time I was in the club was during the final phases of construction in 2003. Its sheer enormity overwhelmed me then, and it still does. I mean, he built a club that holds more people than the Fox Theatre, and built it explicitly as a venue for him to perform.</
When he arrives (90 minutes after our original meeting time, which, for him, is good) we greet each other with a hug. He has such a disarming smile, and it’s impossible to stay angry at him. He is tall and lanky, with a Keith Urbanish haircut complete with blond highlights, and eyes that are focused and intense. His clothes, even his jeans, are custom-tailored to ensure a perfect fit.</
We walk back to the small rehearsal room he’s had built in the back of the club to do something we’ve never done before: talk as journalist interviewing singer. It allows me to ask questions I’ve never asked before, and I quickly realize I don’t know my brother as well as I thought I did. Our lives have had more parallels than I’d realized. Like me, his entire identity in high school was music. We each had garage bands; we each worked as roadies for local bands. After college, we each veered away from music – me into journalism and he into a data-collection business he founded with one of his college friends.</
In the meantime, the three youngest kids all scattered away from home – Bill to Gwinnett County, Mimi to Phoenix, me to Macon and then Rhode Island. When Mimi returned in 1997 after a long absence, Bill hatched another one of his grand schemes: a band called the Gentrys. “She and I had grown apart because she was living in Arizona, and I thought a good way to get to know each other again was through music, for us to sing together,” he says.</
Their first paying gig was at the Country Star in Buckhead, now the ESPN Zone. The room was filled with all of Bill’s frat brothers and every friend he could convince to come out. As first gigs go, it was pretty dreadful. Their “band” was a bass player.</
“I still have nightmares about that night,” Mimi recalls. “We played three sets of 10 songs apiece, and every song had a bass solo.”</
For Bill, the duo with our sister may have begun with a noble motive, but quickly evolved into a different monster. Mimi remembers Bill making her promise that she’d stick with him until they reached Nashville.</
Bill had made a fortune with his data company, and had money to spend to promote the Gentrys, and hired the best musicians he could find for the backup band. He paid, conservatively, $20,000 in 1998 to produce a self-released CD of all-original songs, never mind that neither one of my siblings were songwriters. “He said he’d done market research on hit albums and told me what songs he wanted,” Mimi says with a laugh. “There had to be three slow songs, one in a minor key, three midtempo songs and one song with a double entendre.” They dashed off seven new songs and hit the studio three weeks later.</
The clichéd titles tell it all: “Playing With Fire,” “In Case of Emergency,” “Don’t Try This at Home,” and, the double-entendre song, “This Dog Will Hunt.” The CD also featured an homage to the old Georgia state flag called “Stars and Stripes.” Even Bill is embarrassed by it now. “That album is so far buried now, it’s not even funny,” he says.</
But there was one moment of truth. It was a ballad in a minor key, a song he wrote when he was 19. The first lines were wrenching: “God left a little boy / With nothing but his toys / And no dad to show him how to use them.” Mimi played that song for me not long after they’d recorded it, and there was a long silence – we both felt awkward at the emotional rawness of the words.</
As painful as it was to listen to the song, it was also the first time I saw something in his music that was personal and true, not contrived. And for that, I had to give him a brotherly nod in appreciation.</
MIMI LEFT THE Gentrys in 2000, the same year I retired my blues band. The long hours were getting to her, as was Bill’s single-minded determination with Nashville, no matter the cost. “Mimi said she was either going to kill me or bail,” he says. “In her words: She liked me much better as a brother than a partner.”</
For Bill, it was a moment of decision in ways that maybe no one in the family understood. “I realized that the person I’d been for the past seven or eight years, that wasn’t me,” he says now. “They weren’t things that were bringing me happiness. I had to decide if this was something I was going to do because it was my heart. And I decided I was going to jump in the deep end and go after it.”</
So he kept the band together, put his name out front and played in just about every venue in the region he could find.</
My first taste of his budding celebrity was when I went to see the Kentucky Headhunters at Cowboy’s in Kennesaw, then the biggest country-music club in Georgia. I walked in and did a double take; everywhere I looked I saw banners that read “Bill Gentry & The 35 Cent Rodeo.”</
In addition to his gigs at Cowboy’s, his group also became the house band at a club in Gainesville called Wild Horse. That’s where he truly began to build his following. Bill Gentry and the 35 Cent Rodeo played there three out of four weekends a month. The club advertised on radio. Between that job and his gigs at Cowboy’s, Bill had become the hottest new thing on the Georgia country scene.</
Here’s something else you should know about my brother: The best way to get him to do something is to tell him he can’t do it.</
For example, he closes every show with “Will the Circle be Unbroken,” the Gothic country classic about death and reaffirmation of life. He sings the song as a tribute to his father, but it has even deeper roots in our family history; our family had joined hands and sung that song around our grandmother’s hospital bed as she breathed her final breaths.</
Someone at Cowboy’s told him not to do the song – and especially not his religious-flavored spoken introduction – because he was in a bar and not a church. “That song’s not negotiable,” he told them. Finally they compromised; he could sing it, but he would pull back on the spoken-word intro that talked about God.</
But my brother was not happy that someone was trying to dictate what he did on stage. And then, two weeks later, the Cowboy’s house band hired away his fiddle player.</
Enough was enough.</
He grins sheepishly at the memory. “They don’t know this, but that’s when I decided I was going to build my own club,” he says. “A place where we’d have the freedom to do our music the way we do our music. And to be in competition with them.”</
ONCE HE DECIDED to open a country-music club, Bill Gentry flew around the United States and visited every major country-music venue in existence. He met the owners and learned from their successes and their mistakes. One thing he knew all along: He wanted his club to be big with a capital “B.” “When I made the decision to open a club, I knew the only way we could do it was to be the biggest club in the U.S.,” he says. “Because I knew if we were almost the biggest, I’d be disappointed down the road.”</
It was the same kind of drive his father had, an obsessive desire to succeed and to please everyone. “Our daddy was driven like crazy, never resting,” Mimi told me. “He had a heart condition and he literally drove himself to death. Momma always worries about Bill doing the same thing.”</
For his nightclub, Bill found an abandoned Service Merchandise store by Gwinnett Place mall that had 72,000 square feet of space. He coaxed an investor to go in with him on the club, and began the arduous chore of turning a big-box store into a first-rate venue. It’s a club whose very existence rested on his shoulders, because he planned to perform there himself three nights a week.</
At first blush, it seemed like madness. But when Wild Bill’s opened in May 2003, it caused a huge traffic jam all around the mall. “The opening night was surreal,” Bill says. “About 5,500 people came through. It was the largest crowd that I had ever played in front of. The adrenaline rush was unbelievable. But, mostly, there was massive relief that people had shown up.”</
Here’s something else you should know about my brother: When it comes to luck, he makes his own. Like the Great Peach Campaign. Or, like the time he flew to New York City to attend the 2005 Country Music Association awards show.</
He ran into a friend from Atlanta who had flown up on his private jet. And after the show, he invited Bill to fly back to Atlanta on the jet. Sitting across from him on that flight was Don Perry, who happened to be the right-hand man to the most powerful music lawyer in the business. By the time they reached Atlanta, Perry was so taken with Bill that he offered to set up a meeting. And days later, he met Perry’s boss – Joel Katz, who represents stars ranging from Willie Nelson to Christina Aguilera to Dallas Austin.</
Perry says he was won over on the jet to Atlanta. “Bill’s got a great personality and just exudes confidence,” says Perry. “If that kind of person can translate his personality to the stage, then he’s got something. And when I saw him perform, I saw that same exuberance in his stage show.”</
Katz was also taken in by his bravado. “Bill is smart, he’s talented, a business success and a creative success,” says Katz. “He has a real shot to dramatically show what he can do.”</
It was Katz and Perry who enlisted Charlie Brusco – whose list of clients includes Lynyrd Skynyrd, Styx, Peter Frampton and Bad Company – to manage Bill’s career.</
When I heard those names, I knew it was going to happen. People like Joel Katz and Don Perry and Charlie Brusco don’t suffer fools.</
It became obvious that my little brother might actually reach his dream of a Nashville record deal. But he was also learning an important lesson: The closer you get to the top, the harder the climb becomes.</
IT TOOK HIM 10 years, but my brother finally invited me to sit in with his band last year. “I was afraid you’d say no,” he confessed a couple of weeks ago.</
Maybe he’s right, but I’m glad I said yes.</
Countless women screamed when he walked on stage with his band. The crowd sang along to songs they’d never heard even once on the radio. When my brother raised his hands and swayed them back and forth on a slow ballad, the audience mimicked him and there was a sea of swaying hands before us. He captivated the crowd, running across the huge stage he’d built and leaping off the drum riser like Springsteen and handing out T-shirts the way Elvis used to hand out scarves.</
The surprise was the music. These songs were smart and fun and full of radio-friendly hooks. They were ... dare I say it? ... good. Southern rock with twang.</
When he first put together the Gentrys, it seemed to be all about the thrill of trying to pull off the impossible. But as the years went by, he learned that part of the deal was having the music to pull it off. He made some smart moves. He surrounded himself with the best musicians he could find. He got his songs from Nashville songwriters, and showed a keen ability to pick ones that sounded as if he’d written them himself. He worked hard to improve his voice.</
After the show, one of his closest friends came up to me. “I’m so glad you played with him tonight,” she said. “Your approval means so much to Bill.”</
It had never occurred to me that maybe I had withheld the very thing he wanted the most from me. And that I wasn’t the only one whose approval he wanted.</
An interview can sometimes turn into a confessional. And when my brother and I sat in the rehearsal room, we talked deep into the night. At the end, I put away my notepad, and he spontaneously began to talk about his father. “I think my life has been about chasing the ghost of someone I never knew,” he said, as if revealing a deep truth that took him years to nail down. “Wanting his approval and his love, and wanting to make him proud of me.”</
MY BROTHER PLAYED his “farewell” show at Wild Bill’s in January in front of 5,000 people crammed into the club. He’s hired several young singers who rotate at Wild Bill’s, and he works with them behind the scenes to teach them what he’s taught himself through the years.</
He returns to Nashville in a couple of weeks to record four or five songs with überproducer Garth Fundis, best-known for Sugarland’s mega-hit debut CD, Twice the Speed of Life, and for his long association with Trisha Yearwood.</
“He’s going to have his shot, and he deserves it,” says Joel Katz. “He has to make the transition from a live performer to a recording performer. But Garth is very busy; he would never have taken the project if he didn’t see something there.”</
Charlie Brusco is less cautious. “These songs he’s about to record are going to lead to a major record deal,” Brusco says flatly. “I think he’s going to have hits on the radio. Over the next six to eight months, everything he’s done for the last few years will come together. An act that puts on a great show and has hit records, they end up having a career. Bill knows how to put on a great show. All we’re looking for is a hit.”</
This is do-or-die time for Bill, the moment he’s been building toward since he proclaimed 10 years ago that he was going to be a country star.</
On one hand, he says if he doesn’t make it, he’s satisfied with what he’s accomplished. He’ll have Wild Bill’s, and he might transition into someone who grooms others for Nashville.</
But I don’t believe it for a second. He’s already purchased a huge tour bus and vows to go on a national tour in September no matter what happens in Nashville. He declares that if he doesn’t get a major-label record deal, he’s got a backup plan: Just as he built his own club when Cowboy’s wanted to dictate his music, he plans to create his own record label if the Nashville establishment turns him down.</
If he does get rejected, he doesn’t plan a small, vanity label – he wants to compete with the labels that passed him by.</
Of course, I would expect nothing less. You know my brother – never anything on a small scale.