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”)
Entertainment
Zoe Kravitz teases fans with ring in wedding finger
Zoe Kravitz has set off a fresh wave of speculation after being spotted wearing a ring on her wedding finger during a recent outing with Harry Styles, a detail that quickly caught the attention of fans.
The actress was seen strolling arm in arm with the pop star in Rome, looking relaxed and affectionate as the pair enjoyed time together, with the ring adding fuel to ongoing engagement rumours that first surfaced weeks ago.
The 37-year-old actress appeared comfortable and content alongside her 31-year-old boyfriend, choosing a casual look that included a cape-style jacket and a bright purple scarf.
As spotted by The Sun, Styles kept things low-key in a long grey coat, sunglasses resting on his head, while carrying a shopping bag after a stop at a jewellery store during what appeared to be a Christmas shopping trip.
The timing and setting only added to the curiosity surrounding the gold band on Kravitz’s ring finger.
The couple’s relationship became public earlier this year, with reports revealing they began dating casually in August after years of friendship.
An insider offered insight into why the couple seems less concerned about public attention this time around, saying, “Harry is a very private man – it’s no secret he’s dated lots of people but it’s not always so public.”
“If he wanted to, Harry knows exactly how to keep things underwraps. He’s been in this industry a long time and he knows how his fanbase reacts to things,” the source added.
“He doesn’t take introducing the world to a new girlfriend lightly. He has thought long and hard about it but he’s prepared for the backlash because he thinks Zoe is the real deal.”
The insider added, “It’s never easy for someone to date Harry and they’ve definitely chatted about what it will be like – and Zoe is fully on board. It’s not just a fling and them happily being snapped really shows that.”
Both stars come from recent high-profile relationships.
Styles previously dated director Olivia Wilde, while Kravitz became single in October 2024 after ending her engagement to actor Channing Tatum.
For now, neither has commented publicly on the ring, but the subtle detail has already spoken loudly to fans watching closely.
Entertainment
Paul Feig never expected this from Taylor Swift
Paul Feig went into the final stages of his latest film fully prepared for disappointment, never expecting Taylor Swift to say yes to a song he believed was too perfect to be approved.
But to his surprise, the pop superstar not only watched the movie, she signed off on the track he had hoped for all along.
Speaking during the red carpet premiere of The Housemaid on Monday, the four-time Emmy nominee admitted he had little faith that Swift would clear the use of her 2017 Reputation track I Did Something Bad for the film’s shocking ending.
As Feig explained, securing a Taylor Swift song is never simple.
“Well, that’s the thing; you want to put a Taylor song in your movie, but she and her company have to approve it,” he said while discussing the editing process.
Even with that reality in mind, Feig and his team took a chance.
“So, we were tempting with it, and we were like, ‘It’s so perfect, but she’s never gonna clear this,’” he added.
The unexpected twist came after Swift and her team were shown the finished film.
“Then we showed she and her people the movie, and she approved it. So, I guess she likes it. Thank you Taylor!”
The approval turned a long-shot wish into a defining moment for The Housemaid, which is now playing in theaters.
The film’s soundtrack leans heavily into emotionally charged and recognisable music, blending Swift’s song with tracks like Lana Del Rey’s Cinnamon Girl, Renée Rapp’s Why Is She Still Here?, Kelly Clarkson’s Since U Been Gone, and Linda Ronstadt’s Tumbling Dice and Blue Bayou.
Based on Freida McFadden’s 2022 novel, the thriller stars Sydney Sweeney as Millie, a housekeeper who steps into what appears to be a flawless household run by the Winchesters, played by Amanda Seyfried and Brandon Sklenar.
As the story unfolds, dark secrets begin to surface.
Entertainment
Prince Archie and Lilibet tipped for future roles in Sussex charity
Prince Archie and Princess Lilibet are quietly stepping into the spotlight, with hints they may play future roles in the Sussexes’ newly rebranded charity, Archewell Philanthropies.
The organisation, originally launched as the Archewell Foundation in 2020 following Prince Harry and Meghan Markle’s departure from royal duties, has now marked its five-year milestone with a fresh name and a subtle family-forward message.
To mark the occasion, the charity released a celebratory video reflecting on its work over the past five years and fans were treated to a rare on-camera appearance from Archie, six, and Lilibet, four.
The siblings featured alongside their parents during a recent visit to Our Big Kitchen Los Angeles, offering a glimpse into the Sussexes’ hands-on approach to community work.
In the heartwarming footage, Archie is seen earnestly scooping ingredients from a mixing bowl while Lilibet watches attentively from the counter.
Archie opted for a bright yellow long-sleeved top, while Lilibet stole the scene in a sweet tartan dress, her flame-red hair styled in a Rapunzel-like plait that eventually came loose as she busied herself in the kitchen.
According to Archewell, the family visit focused on preparing and packaging meals for people experiencing food insecurity.
Our Big Kitchen LA, a community-run nonprofit, typically produces around 70,000 meals for schools, shelters, senior centres and local organisations.
When it comes to parenting, Prince Harry and Meghan have made kindness a non-negotiable family value and Archie and Lilibet are clearly getting the message early.
Back in 2022, Meghan offered a rare glimpse into their hands-on approach during an interview with The Cut, when she invited journalist Allison P. Davis along for Archie’s school pick-up.
The moment captured everyday lessons with lasting impact. “If Archie forgets to say please or thank you, Meghan gently reminds him that manners matter,” Davis wrote.
At one stoplight, Meghan was seen retrieving a brand-new backpack from the car boot and asking her security team to pass it to an unhoused man nearby.
The Sussexes, Davis noted, explain to Archie that some people live in big homes, some in small ones, and others are temporarily without one at all.
The family even prepares care kits stocked with water, peanut-butter crackers, and granola bars to give out.
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