How Sting & Shaggy Came Up With Idea For Sinatra Reggae Covers (Hint: Beers Were Involved)

American singer and actor Frank Sinatra remains a topic of discussion among other great musicians, two of which happen to be Shaggy, and former The Police frontman, Sting. The latter conceptualized an idea to cover The Sinatra Songbook ‘in a Reggae style’ for a new album titled Com Fly Wid Mi—after the most random occurrence in Norway with Shaggy.

In a Q&A video sent to DancehallMag (watch it below), Sting recalled how the concept went off like a lightbulb after learning that the Jamaican megastar was a fan of Sinatra’s music.

“About three years ago, Shaggy and myself, Sting, were on tour in Europe and we were in Oslo and it was a nice day off so we rented a boat and we went into the fjord,” the British singer began, with legs crossed—completely juxtaposing Shaggy’s comfortable manspreading—on an outdoor swing.

“We had a few beers, yeah, and there was a record player, you know, like a CD player. It was playing Frank Sinatra’s greatest hits. So, I come out of the water and I’m heading back into the boat and I hear somebody joining in with Frank Sinatra, and it was this man (points to Shaggy),” he said, adding that the song being rendered was Come Fly With Me.

“It sounded pretty good because you have the same kind of voice as Frank…he’s a baritone tenor; not a tenor, but a baritone so Frank had that fantastic tone, but in a high range. I think, ‘Shaggy, you like his music?’ And he was like, ‘yeah.’ And this little light went off in my head and I had this idea in my head. It may be the craziest idea I’ve ever had, and I’ve had a few. But I thought, what about Frank Sinatra Songbook, sung by Shaggy, in a Reggae style. Who’s ever done that before?,” Sting recalled.

The 17-track project will debut on May 25 on all digital platforms. The new album boasts reggae interpretations of some of ‘Ol’ Blue Eyes’ most beloved songs, kicking off with the uplifting ode to resilience That’s Life, followed by Come Fly with Me. The album also includes the sultry, That Old Black Magic, the metaphoric euphoria of being in love embodied on Fly Me to the Moon, and the misery of lost love on Angel Eyes, Luck Be a Lady, Witchcraft, and Under My Skin.

Sting noted that a Reggae collection of Sinatra’s hits was fitting because of the mood the genre evokes on listeners.

“There’s a joy about reggae. There’s an energy about it which is similar to the energy that Frank’s music had in the late 50s and early 60s. So, I said let’s try it. We got some really good Reggae musicians; I’ll bring some guys from the jazz world and combine it…we’ll thread this needle,” Sting said.

When asked why they decided to follow through with the idea of compiling a Sinatra-inspired album, Shaggy did not hesitate to say it was a “why not?” situation.

“It’s us getting together and doing some crazy s–t, because we enjoy that and we like to shock people,” he said as he burst out laughing. “And literally, we’re both allergic to boredom and we’d do anything to make us not be bored.”

Mr. Boombastic, who copped a Grammy Award for 44/876, his last collaborative project with Sting, said he has been exposed to Sinatra’s sound for two decades.

“Frank has been in my home as a child. I don’t know if you noticed, but in my home in Jamaica, I would say around 20 years that we started Irie FM where they played old Reggae—it used to be on Sundays where they played Frank Sinatra and on major radio stations in Jamaica at that time, Sunday was the major day you heard Sinatra, Bill Crosby, Nat King Cole, was always played on there,” he said as he turned to Sting, relaying the memory.

Sting, who is seemingly very excited about the album, is pleased that they are the first to undertake something like this. He said they also collaborated with American record producer, Rob Mathes.

“Rob is my long time friend…an incredible musician. He loves and respects the original material. (There is) a sense of honour. You wanna honour the material and not make a mess of it.”

For Shaggy, experimenting with international genres and amalgamating them with his own native genre was seamless, according to him.

“I’ve been doing hybrids my whole life. I mean, Oh Carolina was done by the Folk Brothers…I covered that but what I did was bring my own style to it and what I did was a hybrid and I sang kind of in the Queen’s English…it’s a mixture of patois and the Queen’s English. Same thing with Mr. Boombastic.…”

For the new album, the pair – both managed by The Cherrytree Music Company — selected a slew of other reggae, jazz and mainstream musicians including Diwali riddim producer/musician Steven “Lenky” Marsden, who arranged the songs.

Recorded in Miami and Jamaica, Com Fly Wid Mi was engineered by Grant Valentine, Earl Smith Jr. & Garfield McDonald, and mixed by Robert “Hitmixer” Orton.