Why Shaggy Feels Like He’s “Won The Lottery”

Halfway into Shaggy’s SummerStage concert in New York City, as 5,000 reggae lovers swayed side to side on a warm July night, Mr. Boombastic abruptly cut the music. “Stop! Stop! Stop! Stop!” he roared. “We are in Central Park!”

“Facts,” his hype man replied.

“This is New York City.” 

“Facts.”

“House full of Caribbean people.”

“Facts.”

“Why y’all acting like this is a damn opera?”

In a time-honored reggae tradition, Shaggy’s band ran the tune back from the top, launching into an uptempo remix version of “Til A Mawnin,” Shaggy’s latest collab with the iconic musician and actor Sting (the two won a Grammy for their collaborative 2018 album 44/876). The audience responded with even more energy, waving their cellphones and lighters in the air.

A master showman who’s been working crowds all over the world since the early ’90s, Shaggy’s been perfecting his onstage banter for almost 40 years, but there was another layer to this particular routine. The last time Shaggy performed in New York he and Sting actually were at the damn opera—the Metropolitan Opera House to be specific, where Shaggy portrayed the Wallsend Ferryman in Sting’s musical The Last Ship—if you know you know.

“I’m allergic to boredom,” says the 57-year-old artist whose breakout hit “Oh Carolina” topped the UK pop charts in 1993. “The older I get, the harder it is to stay inspired. So you pull inspiration from everywhere. If I’m doing the musical with Sting and I pull inspiration, which is great because it’s new. I’m pulling inspiration from people who are masters of that craft, and try to use them as the bar to beat, you know what I’m saying?” He’s also been shooting a movie with Kevin Costner, Honeymoon with Harry, alongside Jake Gyllenhaal and Rita Ora—as well as starring in a 2021 Superbowl halftime show ad for Cheetos, portraying Sebastian the Crab in Disney’s The Little Mermaid Live, running Shaggy’s Boombastic radio on Sirius XM, and establishing the annual Island Music Conference, an industry convention that brings international opportunities to Kingston’s aspiring music biz players.

Music will always be his first love, and last night’s SummerStage performance demonstrated that Mr. Lover Lover is still at the top of his game. Joined by day-one sparring partner Rayvon for dancehall classics like “Big Up” and the #1 pop single “Angel,” Shaggy flowed seamlessly into more recent hits like “Mood,” a collaboration with Trinidadian soca legend Kes, and “Looking Lovely,” featuring Robin Thicke, the lead single from Shaggy’s new album Lottery. Dressed in dark shades and a slick black suit, Robin Thicke raised the temperature with “Blurred Lines,” climbing off the stage and into the crowd as they sang “you’re the hottest bitch in the place.” The few high-profile features who couldn’t make it in person—Sting, for one, Sean Paul and Spice for “Go Down Deh,” and Akon and Aidonia for the Lottery single “Boom Body” — were represented via a giant video screen behind the stage. 

In an exclusive interview with Boomshots correspondent Reshma B, Shaggy took a moment to reflect on his life’s journey leading up to the release of his first true Shaggy album in seven years—not counting Come Fly Wid Me, his 2022 album of Sinatra covers, or the 2020 holiday album Christmas in the Islands. 

“This is the first album where I’ve done a lot of mainstream collaborations,” says Shaggy. He notes that some of his biggest hits were recorded with relatively unknown artists—the hook on “It Wasn’t Me,” for instance, was sung by a dude named Rik Rok. “I just figured that I’ve been, what, 30 years in this? I think I’ve earned the right to get some help,” Shaggy says. “But the help that I’m getting are friends of mine. You know, like Sting is not a collaboration. Sting is my brother.” Shaggy also has genuine chemistry with R&B heavyweights Robin Thicke, Akon, and Jeremih, as well as Jamaican stars Beres Hammond, Dexta Daps, Aidonia, and 450.

Shaggy never fit the cookie-cutter template of a reggae and dancehall star. Although his music career began in New York, Shaggy was born in Jamaica and lived in the rough downtown Kingston neighborhood of Rae Town before moving to Brooklyn as a teenager. Soon after arriving in New York, he enlisted in the US Marine Corps and served as an artilleryman during Operation Desert Storm. He recorded his first songs with ace producer Sting International (not to be confused with the other Sting) during weekend leave, sometimes showing up at the studio in his uniform. His remarkable accomplishments—selling 40 million albums, topping the UK pop charts four times and U.S. pop charts twice, and popularizing the slang term “Big Up” with his 1992 song of the same name—are sometimes downplayed by reggae and dancehall purists. There was a time when this bothered Shaggy, but after all these years he’s definitely come to peace with exactly who he is.

“There’s three types of music,” Shaggy says. “There’s dancehall music, there’s reggae music, and there’s Shaggy music. I’m doing Shaggy music. I’ve done hybrid music my whole life. I’ve been criticized for it when I started to do it. People was like, ‘What the fuck is this?’ I’ve always been a guy that goes against the grain. I’ve always made disruptive music. And I do it selfishly to please myself.”

And the fans who packed the SummerStage show in Central Park—some of whom were not even born when Shaggy started making music—wouldn’t have it any other way. 

Describing Lottery as “100% unapologetically me,” Shaggy advises listeners not to expect any departure from his signature style. “If you go buy this album to get some sort of trend, you know, whether I’m doing trap music or Afrobeats or whatever, you’re not going to get that,” he says. “You’re getting a 2026 version of Shaggy.”

He says the title of his new album has many meanings. “It’s about betting on yourself,” he says. “It’s about showing everybody that you can be at your full potential.” But most of all, he called the album Lottery because he feels like he has won the lottery in life. 

“I’ve been won the lottery,” he says, reflecting on his life’s journey. “I won the lottery from day one. From the day I left outta Rae Town in a tenement yard and moved to New York, I won that lottery. You know, I’m a winner from that day on, man, you know? Jackpot!”