Shaggy has been such an unwavering global presence in music that it’s hard to believe he’s just unveiled his first album of new, original, non-holiday music of the decade.

Lottery, which arrived on May 15 via a partnership between VP Music Group and his own Ranch Entertainment, finds the Grammy-winning dancehall legend proving he can still toast with the best of them four decades into his storied career. Shaggy began working on the 13-song set “around seven or eight years ago,” but his attention kept getting diverted to new opportunities.

At the turn of the decade, Shaggy stepped in to help straight out dancehall queen Spice’s VP Records deal, ultimately signing on to executive produce the Grammy-nominated record. Titled 10, the star-studded project also spawned “Go Down Deh,” an international smash collaboration between Spice, Shaggy and fellow Jamaican crossover sensation Sean Paul that’s collected over 103.7 million official on-demand U.S. streams, according to Luminate. By 2022, Shaggy teamed up with longtime friend and collaborator Sting for Com Fly Wid Me, another Grammy-nominated record that found the Kingston-born superstar reinterpreting the Frank Sinatra songbook in a reggae style. The following year, Shaggy tapped soca sensations like Kes, Bunji Garlin and Patrice Roberts for his genre-blending In the Mood EP.

As a natural creative, Shaggy’s endeavors extended into the theater world by 2025, when he signed on to Sting’s The Last Ship musical, joining a rebooted version of the production in a custom role for international performances in Paris, Amsterdam and Brisbane. At the close of that year, he also co-headlined a benefit concert to raise funds for recovery efforts in his home country following Hurricane Melissa.

“At some point, Chris and Randy [Chin] from VP [Records] gave me a deadline, so I had to [stop] abandoning the record,” Shaggy tells Billboard, just hours before borough president Antonio Reynoso declared May 19 “Shaggy Day” in Brooklyn. “But coming off ‘Go Down Deh,’ the building was very excited about putting out a new record, so everything fell into place.”

Boasting a star-studded lineup of collaborators, including Robin Thicke, Jeremih, Dexta Daps, Sting and Anthony Hamilton, Lottery is a convincing return to form for Shaggy. He honors his sound system roots with “Til A Mawnin,” delivers a sly sequel to “It Wasn’t Me” with “Bun (She Love Me),” and even links up with new-school talent like 450 on the infectious “We Love Di Gal Dem.” Perfectly sequenced for the pre-game, main fete and post-party wind down, Lottery is the culmination of four decades of Shaggy betting on himself — and coming out on top every time.

Below, Shaggy breaks down his new album, reflects on Flatbush’s glory days and dishes on delving further into the acting world.

What was the last song you added to the track list? Why did it make the album feel complete?

The opening track, “God Is Amazing,” was the last record added, not because I didn’t want it — it was done earlier — but because I didn’t want it on the album without the right sound. I had other singers on the hook, but the feeling was missing.

There’s a young lady named Vanessa Amarosi, whom I came across while watching her sing Annie Lennox’s part for a Eurythmics set at Night of the Proms in 2024, and she’s so dynamic. I didn’t even know she was a big singer in Australia, but I was taken by her massive voice. I got friendly with her and her manager, played her the record, and she called me back the next morning with her recording. She cut it in the bathroom of her hotel. She just went into full church mode on it, and that made the album complete.

Was it always meant to be the opening track?

No. But after Vanessa’s vocals came in, the whole team was like, “This is what you should start with.” And then [acclaimed Jamaican dub poet] Mutabaruka was on there, so it just felt like something to open it. It’s almost like praying before you go on stage.

When and how did you land on the album title?

Normally, when I’m doing an album title, I look at the tracklist and see what title fits the story of each record. I also knew I wanted it to be one word, like Boombastic. If you listen to the song “Lottery,” it’s probably the most shallow song on the album, but in the context of the title, there were ways I could spin it.

In the music business, there’s no clear-cut way to success, so it’s really like playing the lottery. It’s like gambling at this point, but I’ve always bet on myself because there was no record company when I started that was thinking of giving dancehall artists a marketing budget. There was nobody before me having that kind of success. In the early stages of my career, the label would always fight everything that I put forward.

For instance, “Mr. Boombastic” was the B-side to “In the Summertime,” which [the label felt] was a more popular record. I had done “Oh Carolina,” and there were a bunch of big records at the time using a similar beat to Chaka Demus & Pliers’ “Tease Me,” so the record company wanted me to do so as well. In hindsight, I probably should have, because I would have made money, but I was young and a creative, so Sting International and I brought them “Mr. Boombastic” instead. I was labeled as being difficult, and the compromise was making that song the B-side. And then “Mr. Boombastic” became the bigger record worldwide.

There’s a lot of Bill Withers on this album. Why was he such a major influence on this album?

When Sting and I did the 44/876 tour [in 2019], we would freestyle for soundcheck. He’d start playing different bass lines, and sometimes we’d end up on a Bill Withers song because we’re both big Bill Withers fans. When he asked me to do Sinatra songs in reggae, he taught me how to sing. I wasn’t confident enough to say that I was a singer.

He would play every note on the keyboard, so I could hear what I was supposed to be hitting. That challenged me vocally because I couldn’t hear those in-between notes normally. Dancehall is two chords, and now I was dealing with six, sometimes seven chords. Sting taught my ear how to pick up on that, and my confidence started building.

When I was doing this album, I decided to flip “Ain’t No Sunshine” into reggae as we did with the Sinatra records. I sent the demo to Sting, and he added a harmony that changed the color of the whole thing and made it so great. And when we went to clear things with [Bill Withers’] wife, she was so gracious and lovely.

Why did you tap Dexta Daps for “Dancehall Nice?”

The world has not yet seen what Dexta can really do vocally. He does things in the studio where I’m like, “Why don’t you let people hear this?” But he doesn’t want to blow up too big too quickly, and I get where he’s coming from. You get a hit record, and the leeches come. And you can tell he’s an emotional guy, so he knows his limitations and boundaries.

You’ve scored three Rhythmic Airplay hits from this album — including “Looking Lovely” (No. 32, with Robin Thicke) and “Boom Body” (No. 28, with Akon and Aidonia) — that began with “Til A Mawnin” reaching No. 35. What does that kind of longevity mean to you?

“Till A Mawnin” was a huge tribute to Henry “Junjo” Lawes, who’s arguably the main architect of dancehall. He started to have artists toast on reggae beats, and all the early Yellowman and Eek-a-Mouse records were done with live bands. It wasn’t until King Jammy came in and started to program music with Steel & Cleavy that things changed. I don’t think Junjo even knows how much of an architect he was at the time. He was just a dude that had a lot of ideas and a great ear and knew how to surround himself with great artists.

I actually got a little bit of pushback from Sting [on this song] because the hook wasn’t something he was used to. But he did it for me, because it’s me. And once he heard the final version, he knew I made the right choice putting him on the song. It was so authentic to how reggae singers do it. And it was actually Sting’s first time being on a Rhythmic [Airplay] chart, so I was proud.

Why is it important for you to continue upholding sound system culture?

I started DJing sound systems in Brooklyn, and that’s where I learned my artistry, my stage performance, how to freestyle and how to read an audience. Me and Super Cat used to be running around Flatbush all the time.

It’s crazy because Flatbush is getting so far removed from that time.

You had Starlight Ballroom, but the most gunshots used to be inside of Biltmore [Ballroom]. I remember one night I was crawling on my belly after some shots got fired, and Cat was on the ground like, “Di one time mi decide fi leave my gun, they go shoot up di place.” It was early days, bro, we were all risking our lives for dancehall.

What’s it been like stepping into the theater world?

I learned that Sting is always right — and he’d take joy in hearing that! [Laughs.] He wrote the part for me, and even though it wasn’t something I was super interested in, he convinced me to try it. It’s not something I thought I would be doing at all. But it’s amazing how, after learning my lines, doing live theatre and getting standing ovations, it’s really become second nature, and I can make it my own.

Even when I got the movie role [in Amazon MGM’s upcoming Honeymoon with Harry dramedy], I thought we weren’t going to do it because they were shooting at the same time I was doing The Last Ship in Australia. But it turned out they were shooting in Brisbane! So, I would do the play at night and film my parts for the movie in the daytime. I’m actually going back in two days to finish.

Would you want to do more movies in the future?

It all depends on how I’m feeling. I will probably have to get an acting coach to take it more seriously now that I’m in it. I also got really friendly with Kevin Costner, who gave me a lot of pointers. I had movies when Hot Shot was hot [in 2000] and roles that I turned down. I even turned down my own television show because I was doing things in dancehall that had never been done, and didn’t want anything to derail me.

Really and truly, I just had idiot management around me. I was young as hell and could’ve done both. That’s why it’s very important to have experienced people around you.

Would you want your own biopic?

Probably not. There’s this old saying: Never let the truth get in the way of a good story. Maybe if I’m dead, they’ll do one; it wouldn’t matter to me after that.