Sting and Shaggy always looked like unlikely collaborators, but it’s the collaboration that keeps on giving.

“When you’re with Sting, you can’t say never, especially when it’s him, me … and gin,” Shaggy says. “Who knows what we’ll come up with?”

Shaggy, the Jamaican reggae/dancehall star, and Sting, the British Rock & Roll Hall of Famer, won a Grammy for their 2018 album, “44/876.” They also toured with a show that year and performed a Tiny Desk Concert for NPR in 2019.

More recently, they teamed up for “Com Fly Wid Mi” (2022), an album of Frank Sinatra covers performed by Shaggy and produced by Sting.

Shaggy (aka Orville Richard Burrell) calls Sting (aka Gordon Sumner) the brother he never knew he needed.

“It’s just an unlikely situation,” says Shaggy, 54. “You go into it collaborating with someone you see and admire. It’s a great opportunity, and in the interim I found my best friend.”

Most often, he says, “you find yourself surrounded by people who are not really your friends. They work for you — they’re your inner circle. It takes a minute to find someone who doesn’t rely on you for anything, who’s self-reliant, that person who is into you for you and not what you do and who you are.

“I talk to Sting about twice a week no matter that time zone we’re in.”

They met in 1994 when Shaggy jumped onstage while Sting performed “Roxanne.” They shared an artists and repertoire label representative at the time; they now share a manager.

Shaggy says the idea for “Com Fly Wid Mi” came while he and Sting were on a boat in Norway. Sting jumped into the water; Shaggy refused. Instead, while Sting waded, Shaggy put on some Sinatra music and sang. Sting popped his head up and said, “Dude, you sound like the dude. Wouldn’t it be cool if we did this as reggae?”

The concept made sense for Shaggy, who says that, though Jamaica is the home of reggae and calypso, you don’t often hear those sounds on the radio there.

“My house was filled with Nat King Cole, Frank Sinatra, Mahalia Jackson, Patti Page — my grandmother’s music,” he says. “That’s what she loved. I was raised on that type of music.”

He credits Sinatra with penning some of the best-written songs in the world — iconic, unforgettable tunes.

“A lot of those instrumentals were done by Black people,” Shaggy says. Quincy Jones’ work with Sinatra included producing “L.A. Is My Lady” (1984), his final solo album.

Though he was familiar with the music, “Com Fly Wid Mi” was the toughest album Shaggy has recorded. His discography includes “Pure Pleasure” (1993), “Boombastic” (1995), “Hot Shot” (2000), “Intoxication” (2007) and “Summer in Kingston” (2011).

Sting recorded Shaggy’s vocals for the Sinatra project and helped him through the process.

“I really studied these songs,” Shaggy says. “After the first week of songs, I got the hang of it.

“I had to train myself to hear them. Sting was very helpful in that. He was very patient. Once I told him I can’t hear it, he sat with me. He was patient in teaching my ear to hear that. He has the most amazing ears and one of the most amazing voices.”

He says working with a giant like Sting, in producer mode, allowed for creative freedom. Throughout the process, he says Sting was “fascinated in what I do and how I do it. He’s fascinated with how I can freestyle a song.”

Ultimately, Shaggy says, this is the album he’s most proud of.

“I didn’t know I could do it,” he says. “The real success is when you step outside of your comfort zone.”

Sting told him, “‘You can do so much more with your voice than you are letting yourself do.’”

While “Com Fly Wid Mi” has not been a commercial success, Shaggy says it has been good to him.

“You would not believe the offers I’ve gotten since that record,” he says. “I had Broadway offers, but it conflicted with a tour I already had. It was based on them hearing that record.”

His new album, “In the Mood” (2023), also brings him back to more familiar territory.

“It’s a Caribbean project I just did,” he says. “It’s seasonal music, but I enjoy it even when it’s not in season. It’s not just Carnival music. It’s feel-good music.”

Shaggy is currently on tour with TLC, Sean Kingston and En Vogue for “Hot Summer Nights.”

“It’s a fan appreciation tour,” he says. “If you’re a fan and see a lineup like this, why wouldn’t you go to that? All of the hits are lined up together. ‘How am I not going to that?’ It’s a string of hits and just a great summer thing to do.”