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Bobby Bones vs. Country Music

How a pop DJ conquered the largest, most insular radio format in the nation while feuding with some of its biggest stars

(Getty Images/Ringer Illustration)

Looking to get in touch with a country star? There’s a good chance Bobby Bones has the number — not that he’d ever call them, or want them to contact him either. "I don’t want these people texting me," the radio DJ says. "I don’t want to be that guy who is at all the things, mingling with all the people. That’s the worst."

A socially awkward and painfully honest 37-year-old with a top-rated country radio program that is heard on more than 100 stations nationwide, reaches more than 3 million daily listeners, and often feels more like a confessional than a music show, Bobby Bones is the most widely heard DJ in the format. In theory, country music is the focus of The Bobby Bones Show, but in truth it’s all about Bobby, including his familiar relationships with his longtime cohosts, Amy Brown and Dan "Lunchbox" Chappell; the middle finger he regularly gives to Nashville’s power brokers; and the way his palpable insecurity and desire for acceptance often hang over the proceedings.

It’s easy to write off his loose lips and tendency to overshare as a deliberate radio persona, but Bones simply refuses to play by the rules. He routinely defies country radio. He almost never goes to industry parties. Every Friday he turns his show into a "dance party," during which he plays pop, hip-hop, and whatever else interests him. He asks personal, sometimes intrusive questions to artists during interviews and calls them out if they slight him.

But he is still an employee of iHeartMedia, the largest radio conglomerate in the country, where his own popularity is trumped only by that of Ryan Seacrest. One might assume that Bones is a disruptive presence for iHeart. After all, the FCC once fined the company $1 million after a fake emergency alert played during a 2014 broadcast of his show.

But he’ll tell you, "My company knows what I do." Bones says iHeart has long been his most ardent champion and defender. It’s why he felt so bad about that FCC fine. "That was the hardest part for me," he says. "People really stuck their neck out and said, ‘This is our guy. Let’s invest in him.’ And I really screwed up."

Yet for all his polarizing behavior, his ratings have more than tripled since his early days in Nashville. In the past seven months, his show has been picked up by 12 new stations, bringing him to 108. Last year he released a memoir that topped the New York Times best-seller list, and in November he’ll be the youngest inductee into the National Radio Hall of Fame. Bones has taken over country radio in spite of himself.

Bobby Bones is proud of three things: his career, his individualist streak, and his home state of Arkansas. His modest office at the iHeartMedia radio studio on Nashville’s Music Row is decorated with his personal effects: a massive picture of Tusk, the University of Arkansas’s live razorback mascot, and two framed pictures of Donald W. Reynolds Razorback Stadium. To Bones, Fayetteville, where the school is located, may as well have been the big city.

Bobby Estell was raised 185 miles to the southeast of the university in Mountain Pine, a 770-person town where 25 percent of the residents live below the poverty line. He grew up in a mobile home, where he would fall asleep on the couch to the sound of his mother cracking open a can of Busch as she watched The Golden Girls, though he was principally raised by his grandmother. He briefly knew his biological father, who left abruptly when Bones was 5. Early on, Bones didn’t see poverty as an obstacle. "To me, being poor was easy," Bones says. "I was good at being poor." On days when his mother couldn’t afford to buy food for him, he would bring "fake meals" to school: "brown bags with nothing in them to look like I had something to eat."

Scrawny for his age, he was regularly picked on by his classmates, but he found solace through the small radio that his aunt Cindy bought him for his fifth birthday. He decided early on that he was going to be a radio DJ. "It was weird to me that my friends didn’t know what they wanted to do when they grew up," he recalls. "’Cause I always knew." He became obsessive in his love of talk-show hosts, listening religiously to his local Top 40 radio station, 105.9 KLAZ. At 8 years old, upon discovering David Letterman, he’d stay up late watching Late Night or go to his local library and watch clips of the late-night host’s early gig as a wisecracking weatherman in Indiana. Letterman showed him that oddballs like him could parlay their talents into being revered. He realized, "Wow! People who are awkward can make it too."

Still, he set a low bar for himself, which he credits with leading to his eventual success. "It was OK to fail because I wasn’t expected to have anything," Bones says. "It was like, cool, I’ll go out and fail and be poor. That’s what’s expected of me." No one in his family had attended college, but Bones sensed from a young age that academic achievement was his only avenue to a fruitful career. "I couldn’t afford college, so it was simple: perform well at school and get out of town."

His high school teachers remember him as quiet until a microphone was placed in his hands. "He would turn it all on," his cohost Brown learned after visiting Bones’s alma mater, Mountain Pine High School. "Whether that meant being funny or vulnerable, he was going to do it behind a microphone." Bones talked his way into a job sweeping floors at the local radio station, KLAZ, and was named the weekend DJ when the spot became vacant. The station’s program director, Kevin Cruise, informed the then–high school senior he’d need a radio name. Bones isn’t sure how Cruise came up with his options, but he told the new DJ he had two: Bobby Z or Bobby Bones. He got the name T-Bone as a child during wrestling practice when his pants split open to reveal an erection, so Bobby Estell was henceforth known as Bobby Bones.

He honed his skills working at KLAZ while attending nearby Henderson State University on a full academic scholarship. After graduating, he convinced Little Rock’s Q100 to hire him as their full-time evening DJ, and at that point, Bones knew he would never be as slick or professional or polished as other DJs that he admired. He decided to make his personal life the star of his radio show.

"It wasn’t any brilliant idea," Bones says of the decision that would catapult him to national acclaim. "I just thought, ‘I don’t want to suck forever. And if I’m going to suck I want to suck being me.’ The only thing you own is yourself," he adds. "The only way I was going to be distinguishable from other people is to just be me. Good or bad. Ugly or pretty."

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The Bobby Bones Show as we know it was born in 2013, as Nashville country radio was undergoing a sea change both in terms of content and listenership. Artists like Luke Bryan and Florida Georgia Line were racking up №1 songs, and the term "bro-country" — often applied derisively to artists whose songs had a narrow focus, typically partying and pickup trucks — was first coming into the consciousness.

Country had long been popular with the 25–54 age demographic, but now a younger audience was flocking to the genre. An off-color, outside-the-box personality like Bones was a perfect fit because he had no problem discussing tabloid topics and was an early adopter of using social media to interact with his listeners. "It really was a very fortuitous perfect storm," says Lon Helton, the longtime host of Westwood One’s Country Countdown USA, member of the Country Radio DJ Hall of Fame, and founder of the country music trade publication Country Aircheck. "You put on a personality who is going to appeal to the younger end of an audience and all of a sudden country radio finds it coming to it in droves."

But the Top 40 show that he hosted in Austin at KHFI 96.7 was where the program first built a following. Bones landed the job after executives at the station had caught wind of a stunt he’d pulled in Little Rock. Irritated at his rival station, Alice 107.7, Bones had his sidekick Gilligan sneak into their studio, get on the air, and call Bones, who proceeded to badmouth them remotely via cell phone on the station.

In Austin, Bones refined his on-air persona and doubled down on sharing the most intimate details of his life with his listeners. He’d discovered Howard Stern in college and was drawn to the radio personality’s open-book approach to his personal life. "I liked when he was being human," Bones says. "I strived to be like that."

To that end, on a recent morning’s broadcast of his show, Bones casually told Amy Brown, his best friend and eye-rolling foil, and Lunchbox Chappell, a goofy man-child of a sidekick, that he sits down to urinate in order to avoid dribble. "Now I don’t change underwear twice a day!" Bones declared.

The process by which he recruited his cohosts was as off-the-cuff as his on-air style: Bones met Lunchbox at a bar and Brown at a Culver’s where she was handing out ice cream coupons. Neither had any radio experience: Lunchbox had been a stock boy at Sam’s Club; Brown had been selling granite. Bones says gut instinct alone told him to bring them into the fold.

The show developed into something more akin to siblings roasting one another and laughing at the world than the typical contrived morning-radio banter, and Bones refined a sixth sense for what audiences wanted to hear him and his team talk about. "He had this knack," of knowing what comedy bits or games or discussion topics or even music selections would play well, Brown remembers. "It’s this odd gift. Some people have it. And he’s definitely got it."

The Bobby Bones Show resonated with listeners in a major way: Over 10 years in Austin, it became the top-rated program in the city for nearly every age group, and it landed in syndication in smaller markets, from Wichita to Tuscaloosa. In 2013, the senior vice president of programming at iHeartMedia, Rod Phillips, offered Bones the opportunity to move his show to Nashville and make it the widest-reaching program in the country format.

For Phillips, the decision to bring Bones into country radio was a risky one. The DJ had always been in Top 40, where he’d developed a reputation as a wild card. Country radio listeners, and the industry at large, were traditionally averse to change, so "it wasn’t a no-brainer," Phillips admits. "We were definitely stepping out of the format. Nobody saw that coming." But even if he came from a different genre in Austin, Phillips "always felt like the show wasn’t that far [from] being acceptable to the country audience. … It was a bunch of country people on a Top 40 show."

Bones was confident his show could have worked in any musical format — mostly because he views himself as an outsider. During our time together, he compared his outsider mentality to the label-eschewing hip-hop artist Chance the Rapper. He’s fluent in pop and rock and hip-hop, and for a time he even cohosted a national sports show on Fox Sports Radio with tennis champion Andy Roddick. But he grew up on country music, and the country market was an exciting challenge for him.

Before Bones arrived on the scene, he was convinced the format had gotten stale. So when Phillips and other iHeartMedia executives first proposed moving The Bobby Bones Show from Austin to Nashville — which would increase his distribution to 35 stations immediately and make his show the flagship radio program in Music City — Bones agreed because he thought he could breathe new life into the genre.

"How cocky am I to think that?" he asks now. "But I really felt like that. I felt like I could go in and move it forward a bit in the direction of ‘Let’s catch up with the rest.’"

He came in to fill a vacancy left by the revered WSIX DJ Gerry House. For 27 years, House anchored BIG 98’s Gerry House and the House Foundationbefore he retired in 2010. Honest and revealing, House was well respected by the country music industry and cozy with the Nashville establishment. Bones, by comparison, was an outsider who’d never worked in Nashville or country radio. Almost immediately he fought, in person and on social media, with country record label executives, journalists, and even artists.

In early 2014, Bones exchanged a series of barbed tweets with singer Kacey Musgraves. He accused her of being rude in an interview for his show. Their conversation lasted less than two minutes and never aired in full on his show. But Bones edited out a portion of it and used it as part of a segment he called, "Is Kacey Musgraves Annoyed?" He then took to Twitter:

Musgraves responded.

Bones fired back.

More recently, this year in an interview with Jake Owen on his podcast, BobbyCast, Bones accused the singer of badmouthing him to some listeners in a bar in Dallas. "My feelings were hurt," Bones said. Owen responded by saying Bobby "[stirs] some drama up."

Bones is not exactly apologetic, but now says he realizes such reactionary behavior is more out of defense than spite or malice.

"When I get pushed I tend to push back harder. It’s not a good trait," Bones says. "If I would have just not conformed it would have caused issues. But I was in people’s faces about it. It was obnoxious."

One incident he’s not ashamed of is the time he launched a negative PR campaign against himself. Sensing his show was floundering, he spent almost $13,000 of his own money and put up billboards in highly trafficked areas of Nashville for three weeks that read, "GO AWAY BOBBY BONES." Not until his memoir was released last year did he reveal the stunt was his own doing.

It was inspired by a story he read about Brian Bosworth. The polarizing former NFL linebacker sold "I Hate Brian Bosworth" shirts at away games and "he would make tons of money off it," Bones says with a laugh. "I thought, ‘Man, that’s really smart.’" In Bones’s case, the billboards were "about creating buzz" and "getting people to pay attention to my show. … Good, bad, or indifferent I didn’t care," Bones says. "As long as they’re talking about me."

Bones is fortunate: His reach is principally aided by iHeartMedia’s stranglehold on the radio industry. In the wake of the 1996 Telecommunications Act, iHeartMedia, formerly Clear Channel, "has grown from 40 stations to 1,240 stations — 30 times more than congressional regulation previously allowed," according to a report from the Future of Music Coalition. The only other radio conglomerate that compares to iHeart in its scope is the №2 radio company, Cumulus Media. iHeart owns more than 170 country stations, which makes Bones’s stated popularity a bit misleading, says Lon Helton, the host of Country Countdown USA.

"It’s always hard to tell where the success comes from," he says. "Did you build it one by one or were you born on third base and act like you hit a triple?"

There are other notable iHeart personalities, including Seacrest, Elvis Duran, and Steve Harvey, all of whom command large salaries and the company’s resources and attention, but Bones recently beat out Seacrest in a public vote to become the youngest inductee to the National Radio Hall of Fame. He bristles at any comparisons. "We’re just different. We do different things," he says, before noting that Seacrest has been "nothing but nice" to him over the years.

Even if iHeart’s grasp inflates Bones’s popularity, it doesn’t artificially grow his influence. He’s brought artists like Maren Morris, Kelsea Ballerini, and Chris Stapleton into his studio and played their music on the air while they were still unknown. Chris Janson was an unsigned artist who couldn’t land a meeting in town when Bones began playing his song "Buy Me a Boat" on the air and pushed it to no. 1 on iTunes.

It’s a vital service because even in the streaming age, country radio remains essential to its artists’ careers, and Bones is the genre’s voice and face. As detailed in a recent Washington Post article, country music record labels often spend hundreds of thousands of dollars to introduce their new artists to radio programmers and talent across the country, and there’s a vast landscape to blanket. Country is the largest radio format in terms of total stations; according to Nielsen, it comprises 13.6 percent of total listenership, making it the largest in the country. In recent years country radio has also been one of the fastest-growing formats: Between 2008 and 2015, the number of country radio stations grew from 2,874 to more than 4,000.

There are non-iHeart country radio personalities — including Graham Bunn at Los Angeles’s Go Country, and Trey Morgan and Lisa Taylor at the Cumulus-owned The Wolf in Dallas — with large followings. But as iHeart’s country meal ticket, and therefore the host being heard by more people on more stations than any of his competitors, Bones has a built-in advantage.

Additionally, like Seacrest does with TV and production work, both men also use their radio shows as jumping-off points for outside endeavors, which for Bones is touring with his band, the Raging Idiots, and performing on his Funny & Alone stand-up comedy tour.

It’s all part of his saturation campaign. "I need to be everywhere," he says. He recognizes the changing dynamics of how people consume content, and he doesn’t want to be left behind. "I just try to do as much as possible," he says. "It’s like I’m a bear about to hibernate: I’m trying to eat as much as possible so whenever winter does come, I’m prepared."

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In the ’90s, "shock jocks" the most notorious, outlandish, and provocative radio personalities — such as Stern and Mancow Muller and Bubba the Love Sponge — relied on pranks and profanity and explicit sexual material to attract attention. In the Internet Age, when shocking and downright disturbing fare is readily available, radio talent find themselves looking for growth opportunities outside the medium.

Despite a 2015 Nielsen report that showed terrestrial radio audience hitting an all-time high for the second year in a row, with 245 million Americans using the medium in a given week, the commonly held belief today is that someone like Bones will be left behind if he doesn’t expand into new media platforms. So with iHeart’s financial backing, plus a few sponsors, Bones records his BobbyCast podcast most weeks from an upstairs office bedroom in his sparsely decorated home in West Nashville.

Even though his weekday morning show and a weekend countdown program, Country Top 30, reach a combined 5 million listeners, it’s still not enough for Bones. So he launched BobbyCast last August. To date, he’s recorded more than 70 episodes. It’s a longer, more in-depth format than his radio show, and one that he says inspires more personal, Oprah-like exchanges with the artists and songwriters he brings on.

iHeart was initially worried that this flurry of activity would take away from his radio show, but it quickly came to realize that it only further expanded his reach. According to a new Edison Research report, 67 million Americans listen to a podcast every month. The year-over-year growth rates for podcast listening have also been remarkably consistent, with steady annual gains of three to seven percentage points. And with Apple recently announcing its plans to provide comprehensive analytics about listener behavior to podcast publishers this fall, this trend is likely to continue as more ad money pours into the format.

"When I go to a sold-out 2,000-seat theater in whatever town," iHeart’s Phillips says, "and they’re there to watch Bobby do standup comedy, I think to myself, ‘How did a radio morning guy make this happen?’"

His success comes at a pivotal moment for iHeart. Its first-quarter financial results for 2017 revealed that its more than $20 billion in financial obligations may force it to file for bankruptcy by 2018, though the numbers may be deceiving. The debt is largely the result of a 2008 buyout in which Clear Channel Communications (now called iHeart) was taken private by two private equity firms; despite decreased ad spending on radio, the company’s foray into apps, concerts, and events, combined with sponsorships and licensing, have stemmed the tide.

If the goal for a company like iHeart is to expand its already massive reach, Bones is doing his part. "He can really transcend the other media outlets," Phillips says. "That’s been a win for both sides." Bones has landed a few TV pilots that stalled and died, including one that partnered him with Deion Sanders. But now his focus is on launching his own Nashville-based podcast network this summer and grappling with questions about how to grow an audience.

Even someone like Charlamagne tha God — a hip-hop radio personality who cohosts the syndicated Breakfast Club, is the author of a New York Timesbest-selling book, and is one of Bones’s closest friends and peers — says he struggles with how to diversify his audience in today’s fragmented media climate. He recalls a chat he had years back with Howard Stern’s legendary agent, Don Buchwald. Charlamagne says Buchwald told him in the early days he’d purposely keep Stern off any other media platforms besides radio so as to maintain a sense of exclusivity. "And in the era of Howard, absolutely, radio was enough," Charlamagne says. "But not in this era. In this era you gotta be on social media, you gotta be taking your content and putting it online. You have to go where the people are."

"Today you have a lot more avenues to get yourself started," contends Chris "Mad Dog" Russo, who was one half of the beloved Mike and the Mad Dogsports talk show on WFAN in New York with Mike Francesa. "But," notes Russo, who has his own channel, Mad Dog Sports Radio, on SiriusXM and hosts an afternoon radio show, Mad Dog Unleashed, "there are so many places people can go to get their information and opinions that it’s a little harder to set yourself apart. So you’re damned if you do, damned if you don’t. In the old days there weren’t many places to go to get a chance; today even if you’re great it’s hard to set yourself apart. It’s a very, very tough call."

Bones says there’s still "bad blood" between him and certain factions in Nashville. "You think there wouldn’t be," he muses, "but there doesn’t always come a point" where it ends. "And so I live with it. It’s fine."

Though a second later he admits, "I’d like for everybody to love me. Are you kidding? I feel like everybody should love me. Please love me! That’s all I’ve been doing my whole life — searching for love."

At this point in his career, Bones concedes that outside perception is largely out of his control. He can only continue getting on the radio every weekday morning and doing his job. "If the show gets good ratings, you can only say I suck for so long," he says with a laugh. "You just try to hit your numbers."

Thanks to a long-term deal with iHeart, which Bones signed in 2014, The Bobby Bones Show will remain on the air until at least 2019.

Not that it’s any comfort to him. "I’m just scared it’s going to all go away," he says. The media landscape is forever changing, and Bones doesn’t want to become a relic of a precious era. It’s why he overpays the utility bills for his home and says he often feels like he’s a fraud about to be exposed.

"It’s like I’ve been robbing stores this whole time," Bones says of his monumental career. "I feel like I’m still running from the cops and eventually they’re gonna catch me."

An earlier version of this piece incorrectly stated the details of the 2008 buyout of Clear Channel Communications; Clear Channel (now iHeart) was taken private by two private equity firms.