Entertainment
The true, authentic Kenny Chesney
Just as the sun was going down in the heart of old Key West, Florida, a self-described pirate rode his rust-ravaged bike to the Blue Heaven restaurant to meet a friend – a friend we just happened to be in the middle of interviewing. “She said come in!” David Wegman laughed, as he joined Kenny Chesney.
But that’s the thing about Chesney – down here, he’s not really a country music superstar. He’s just another laid-back local. “We know a lot of the same people,” Chesney laughed.
He collects characters like seashells – he met Wegman at Ivan’s Stress-Free Bar down in the British Virgin Islands. “Above the bar was written in shells: ‘No Shirt, No Shoes, No Problem,'” Wegman recalled.
That 2002 song, “No Shoes, No Shirt, No Problems,” helped make Chesney one of the biggest touring acts around. Almost every summer he turns stadiums into beach parties. Among his many accolades: the Academy of Country Music’s Entertainer of the Year Award, which he won four years in a row. And just last week, he was inducted into the Country Music Hall of Fame – a career-topping accomplishment that he credits to taking that tropical turn in his career.
“You know what’s crazy?” he said. “I had an 18-song Greatest Hits album, and nobody knew who I was. They knew the songs, but I wasn’t comfortable in my skin yet. I didn’t know who I was supposed to be as an artist yet. I would go do shows and they would go, ‘Oh yeah, that’s the guy that sings that song.’ And then, ‘That’s the guy that sings that song.’ When I started being my true, authentic self, that’s when everything changed.”
He could have taken us to some Tiki bar down in the Keys to keep up his tropical brand. But instead, he wanted to show us the room where Ernest Hemingway worked on “To Have and Have Not” and “Green Hills of Africa.”
I said, “The space, it’s almost like sacred place.”
“Yeah, do you feel it? I feel it,” Chesney said. “I spent so much, almost two weeks straight on the bow of my boat in the Virgin Islands reading those books.”
Which might explain why he came down here to work on his first book, out next month: “Heart Life Music.” “This book forced me to pause,” he said.
William Morrow
For all of his love of the islands, he writes it was his own mom who first realized that he may have drifted too far from his East Tennessee roots. “She wanted her 12-year-old boy back in ways, and he was gone. Gone gone gone,” he said.
“She had a hard time finding you, kind of had a hard time reaching you?” I asked.
“It hit me a little bit, but I was so already so addicted to seeking an adventure and all of it, and all these new things happening in my life that I dismissed it.”
He kept going, kept touring, kept writing, until a concert in Indianapolis back in 2009, which he describes as hitting a wall, and crying on stage. “In that moment I was so exhausted and numb to all of it, that it wasn’t making me happy,” he said. “I wasn’t creating the same way. I wasn’t connecting to the audience. It just hit me. It took sports to get me out of that funk.”
He grew up playing baseball and football – loving every inning, every down. So, when a song called “The Boys of Fall” crossed his path, he didn’t only record it; he began interviewing coaches and players about sports and life, and turned it into a documentary for ESPN, “Boys of Fall.” “I needed Joe Namath, I needed Bill Parcells,” he said. “I sat in Bobby Bowden’s living room and he talked to me like a deacon in a Baptist church! I woke up one day, and I went, I’m back.”
Now he’s the one doing pre-game pep talks backstage, like at Sphere in Las Vegas. Many on his team have been with him for decades. There’s confidence in familiarity. “If I had to sit on the bus and think about what I’m getting ready to go do, it would – yeah, I don’t do well with that,” he said.
He put on the kind of show his fans expect – a kaleidoscope of sand, sunsets and songs.
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When me met him the next morning, he was still buzzing about performing in Sphere. “The first couple of nights, I caught myself singing a song and I was like, Well, this is so cool! And then, I forgot the words to a song that I actually wrote!”
On stage with him this night was Grace Potter, the singer-songwriter he recruited for a duet, even though country really wasn’t her thing. The two are now lifelong friends.
“There’s people who have always seen him as just the iconic, you know, Statue of David of country music,” she said.
“I’m gonna go to Florence and stand beside it!” he laughed.
“But there’s just so much more underneath it that’s more interesting than the sculpture itself,” Potter added.
Indeed, the off-stage Kenny Chesney is a more complicated guy, a more thoughtful guy, even a little shy if you can believe it. That’s the East Tennessee part that will always remain even as he’s chasing sunsets.
Chesney said, “It takes a certain amount of ego to be up there on stage and to do what I do, right? But I try really hard to leave that person up there. I can’t live that person every day. And I don’t want that person in my life every day, but I’m really glad to meet him when I go back up there.”
READ AN EXCERPT: “Heart Life Music” by Kenny Chesney with Holly Gleason
WEB EXCLUSIVE: Extended interview – Kenny Chesney (Video)
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Story produced by Aria Shavelson. Editor: Remington Korper.
See also:
Kenny Chesney spreads the love to Boston bombing victims (“Sunday Morning”)
The 2026 NFL Draft was completed with full of trades and surprises on Thursday night, April 23.
In a significant move, the Las Vegas Raiders opted for Indiana quarterback Fernando Mendoza with the No.1 overall pick.
After the first round, some teams are all in on their future, while others are dangerously close to being counted out.
Who’s in
The Las Vegas Raiders are in without a doubt. With the first overall pick, they drafted quarterback Fernando Mendoza, the winner of the Heisman Trophy, who will be the face of the franchise going forward.
All four teams in the NFC East are in contention now. The New York Giants are in after drafting Arvell Reese from Ohio State and tackle Francis Mauigoa. The Dallas Cowboys are in after trading up to select “transformative” safety Caleb Downs. Even the Philadelphia Eagles and Washington Commanders landed top talent.
The Los Angeles Rams are looking to build for the future. By taking Alabama quarterback Ty Simpson with the 13th overall pick, they’ve guaranteed themselves their man under center when Matthew Stafford retires.
Who’s out
The New York Jets didn’t find the right path. Despite having three first-round picks, officials panned their haul, calling edge rusher David Bairly at No. 2 a major reach.
Another setback was the Arizona Cardinals. Selecting a running back like Jeremiyah Love with an underperforming offensive line and dire needs defensively made one wonder if the team had already tanked.
The Miami Dolphins disappointed just as much. Following their spending in free agency on a quarterback such as Malik Willis, they didn’t provide him with anything worthwhile offensively.
Predictions for round 2 and round 3
As rounds 2 and 3 are approaching, analysts make major predictions.
Starting with Round 2, San Francisco will select Emmanuel McNeil-Warren as their safety selection at No. 33 overall, while Arizona selects Carson Beck as a future starting quarterback at No. 34 overall.
Buffalo will be taking a chance by selecting Josh Allen’s red zone target in Denzel Boston at No. 35 overall, while New York adds to their depth with Jermod McCoy at No. 37 overall.
Meanwhile, Baltimore is going for yet another falling star in Avieon Terrell at No. 45 overall. Teams that need a quarterback will watch closely as the Steelers draft Garrett Nussmeier at No. 53 overall.
In Round 3, Philadelphia drafts an offensive tackle to help improve their offensive line with Caleb Tiernan at No. 68 overall, while Cleveland takes care of one more defensive player.
Miami selects tight end Oscar Delp at No. 75 overall, and Pittsburgh looks to continue rebuilding its secondary. As the third round progresses, expect runs on receivers and interior offensive linemen.
Jada Pinkett Smith is asking a judge to order Will Smith’s former friend, Bilaal Salaam, to cover nearly $49,000 in legal costs after parts of his emotional distress lawsuit against her were dismissed.
According to court documents reviewed by TMZ, Pinkett Smith argued that Salaam should be responsible for the expenses she incurred defending herself.
Salaam had filed a $3 million emotional distress suit last year, claiming he was brought in to help Smith with damage control following the 2022 Oscars slap incident involving Chris Rock.
Salaam alleged that Pinkett Smith and members of her entourage threatened him after learning he was working on a memoir.
Allegedly, he was even warned that he could “end up missing” or “catch a bullet” if he continued “telling her personal business.”
He also claimed she pressured him to sign a nondisclosure agreement under implied threat.
Pinkett Smith categorically refuted all such claims calling them “false, uncorroborated and made to generate attention as part of an ongoing public campaign of harassment.”
She further argued that Salaam failed to provide evidence for claims that he lost a girlfriend, left the country, or suffered health issues due to distress.
While parts of the lawsuit have been thrown out, the case remains ongoing.
Denise Richards was able to make some lovely memories with Patrick Muldoon before his sudden death from a heart attack last week.
Muldoon and Richards — who dated in the 90s for five years and remained best friends for decades later — play romantic partners in the new action crime thriller film Dirty Hands, out in theatres on Friday, April 24.
“Pat & I were supposed to do press this week for Dirty Hands” Richards wrote on Instagram. “He was so passionate about this movie & worked so hard on it…We did our first movie together & I am so blessed & grateful I did his last movie with him.”
The post was accompanied by an emotional scene between their characters: Muldoon plays Chicago drug runner Patrick Muldoon and Richards plays his girlfriend Sheila, who is torn between her loyalties.
Richards, 55, and Muldoon, who was 57, first starred together in Starship Troopers in 1997, when they were 19 and 21 respectively. They formed a strong bond and dated for five years before deciding to remain friends.
Earlier this week, the Real Housewives of Beverly Hills star paid tribute to Muldoon on Instagram, admitting she’s “deeply heartbroken and devastated” losing her “best friend” and “family.”
“My whole adult life & I don’t know it without you. The friendship, love, support, respect & loyalty we we had was unconditional and rare,” she wrote. “You’ve had my back and protected me more than anyone. I don’t know what I’m going to do without you here.”
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