How reggae legend Shaggy teamed with Sting to sing the Frank Sinatra songbook

Following the Grammy Award for their collaborative album 44/876, Sting and Shaggy have joined forces again for Come Fly Wid Mi.

This new album, produced by the 17-time Grammy winner Sting, features the dancehall reggae legend Shaggy singing the Frank Sinatra songbook.

The songs on the album include That’s Life, Come Fly With Me, That Old Black Magic, Fly Me to the Moon, You Make Me Feel So Young, Under My Skin and all the Sinatra classics.

The idea of Sting and Shaggy making an all-Sinatra album in a reggae style is just so crazy that it might work — in fact, it does.

Shaggy joined us in the Gumbo Kitchen to talk about the new record.

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Shaggy, how are you?

I’m doing very fine, my brother. Thank you very much. Every day above the ground is a good day.

Hey, you never get any older. This is unbelievable.

You know, I put that to good life and don’t put too much energy on things that aren’t that big. We tend to worry about so much things in life. Sometimes, less is more. We’re put in a position to try and achieve more in life, and the more things we achieve the more responsibility, which brings also more stress. And dealing with people is also more stress, because you’re bringing their energy on also! It ages you. I’m telling you, bro. It ages you. The more you deal with people, it ages you. If something is good, that’s what you rock with.

Let’s talk about your new album of all Frank Sinatra music done in a reggae style, produced by Sting. How did this idea come about?

Dude, it’s such a great idea I wish I could take credit for it. That was all him, man. I just was on this boat singing these songs that were the soundtrack to my life. A lot of people don’t know that in Jamaica, that repertoire was played on Sundays. It was a thing. It goes with the rice, peas and chicken. It’s Frank Sinatra, it’s Nat King Cole, it’s Sam Cooke, it’s Bing Crosby. That’s what was played. And a lot of country, too. Kenny Rogers and Dolly Parton were a big part of what was played on Sundays in Jamaica. So, I was familiar with the repertoire already. I was on this boat and put the music on while [Sting] was in the water. He come back up and hear me singing and he was like, “Bro, that’s your key. It’s amazing how you sound. You’re a bass tenor. Frank is a bass tenor. It’s perfect.” I don’t understand what he’s talking about, but then we started to talk and he’s saying we should do a couple of covers. It just sat around for about three years, until I was in Vegas and he asked, “What are you doing at the top of the year? Let’s go do this.” We flew a couple of musicians up from Jamaica. In the first week, when we started to hear how they were coming out, we knew we really got something here.

How did your relationship with Sting happen?

The first time I actually met Sting was when I jumped on a stage with him in Antwerp in 2004. I was there with James Brown and Cindi Lauper, a bunch of us doing Night of the Proms. I ended up jumping on Roxanne, rocked it, and I never saw him again for years — until I had this song called Don’t Make Me Wait, and my A&R at Interscope [asked me] to send him the song. I was in Los Angeles doing some other project and then I seen Sting walk in singing the song and said, “Come Shaggy, let’s do this. This is a hit record.” I’m like, wow. In that session, we cut the record and we ended up having a conversation that was way more fun than even the work. From that point, he was motivated to not just move on the song but to do a reggae album.

Were you always a Sinatra fan growing up? I guess he was always in your life, right?

What I really liked about a lot of Sinatra stuff was the songwriting. They were really great songwriters who wrote a lot of these songs. Frank had a way of delivering these things. It seemed simple, because he’s not one of those riffers. He’ll just sing it to you straight, effortless. It seems easy until you’re doing it. That’s when you start to realize the genius of Frank’s voice, and of his style, and of how great his ear was. That’s what really moved me. But the songwriting was just amazing. These guys were songwriters that wrote timeless records.

The first thing that struck me when I heard Come Fly Wid Mi was how these two different worlds — Shaggy and Sinatra — came together seemingly effortlessly. The spirit of these songs translate beautifully into reggae. Somehow it works, doesn’t it?

It does! Most reggaes are two chords, and this repertoire has five, six or seven chord changes, at times. So, to make it work without it sounding corny, we had to cut certain notes out. It could easily sound too jazzy, because those are jazz chords, or you might do it where it’s too reggae. We had to have the right blend of jazz to complement the main part of it, the reggae.