Come Fly Wid Reggae Star Shaggy (Part 3 of 3)

Continued from Part Two…

Shaggy: So I put my phone on some Bluetooth. And I have a Sinatra playlist. You know, what a lot of people don’t know is radio stations in Jamaica didn’t start playing reggae music on the radio 24/7 until around the ‘70s. Before that, it was a lot of American music: people like Bing Crosby and Nat King Cole, and a lot of country music. And Sinatra was a big part of my household growing up.

But anyway, Sting heard me sing along with one of the songs. He just cocks his head and says, “Oh, my God, do that again.” And I kept singing. It was like, “That’s your key.” I’m like, “What are you talking about?” He says, “Your voices are so similar.” He’s always just heard me do dancehall reggae things.

And Sting’s like, “Wouldn’t it be great if we would do a cover of that?” And then he said, “Wouldn’t it be great if we do it in reggae?” Then we start talking. Of course we’re having a couple of drinks at this point. And we’re like, “Well, maybe we do an album of it.”

This thing sat around for two years. The world went through Covid, done with Covid, Sting’s playing a residency. I came to see him, and he takes up the guitar, and he started playing a couple of chords from “Come Fly With Me.” I just started singing with him. And he’s like, “We should really do this.” It was about Christmas time. He says, “We should do it in January.”

Sting showed up in Miami at my house and says, “Come, Shaggy; let’s do this.” And so now I’m scrambling, trying to get musicians. We flew a couple people in from Jamaica for the rhythm section, and I was like, “Okay, let’s see what we come up with.” Sting picked the songs that were gonna do, and now we had to figure out how to make those chord changes work in reggae to where it sounded cool and not corny.

And that was where the challenge was, and where the magic came. We averaged about two songs a day on vocals. And within about six weeks, we had the whole project all wrapped up as far as the making of the songs. It was just incredible; we did a couple of shows together, him and me.

Was CCome Fly Wid Me: The Sinatra Songbook Inna Reggae Style pressed on vinyl as well?

No, but we did 44/876 on vinyl. Funny enough you’re saying this. A couple of weeks ago I was over at Sting’s house. He has this wonderful record player and he looked around and it was like,”Yo, we should get this on vinyl.” So that’s probably something that we’ll end up doing.

You’ve got two Grammy awards, and at least six other nominations. Beyond the honor of getting them, do awards, make any real difference in your career?

I don’t think it makes any real difference. But, listen: it feels good when you win, man. I’m not even gonna lie. It’s gonna be hard for a guy like me. You see, I will be nominated six or seven times, but I won’t be the guy getting it because I am not your traditional guy.

And your voters are traditional people, you know, and they’re going to be voting on that Bob Marley style reggae that I don’t particularly make. You know, I represent the genre and I’m from that genre and I respect it and I love it, but I’m not inspired to make it. And the reason is that I look at these guys as masters of their craft. Now, would I be thinking that I could make a record just like Bob Marley and do it better than him? Who am I to think I could be doing it better than Dennis Brown?

I think what’s a better legacy to me is the barriers that I’ve broken down over three decades. “Oh Carolina” was the first dancehall record to ever go #1 in the British chart. “Mr. Boombastic” was the first reggae or dancehall record ever to debut at #1 in the British chart. I debuted again at #1 with “It Wasn’t Me.” And I debuted again with “Angel” at #1 in the British chart. And the Hot Shot album debuted at number one in the British chart. To this day, I’m the only reggae dancehall artist from Jamaica that has a number one Billboard album. No one else has.

We have sold 40 million records. And I was the guy that was responsible to take it to mainstream. And by the way, I did all of this without ever having great executives. You look at great artists, from Springsteen to anybody: They all had great executives who believed in them. This guy don’t. The point I’m trying to make to you is that I have done all of this without having that Tuesday morning conversation, “Let’s put $10 million behind this artist.”

And why would they? There was no track record of reggae being played on radio in that kind of rotation. I am the first. I think that’s a bigger legacy than any award. I rather go for the reward than the award.