Shaggy Credit: Photo: Courtesy of the Pittsburgh Symphony Orchestra

“You never know what a song is going to do,” Shaggy tells the Pittsburgh City Paper. “I can’t believe this record almost didn’t happen, but I knew it was something special because I fought for it.”

The Jamaican born musician is referring to his 2000 hit “It Wasn’t Me.” The catchy lyrics and reggae sound made for a fresh, fun pop banger that became one of the most recognizable songs of the Y2K era.

“I am not a cookie cutter and like to step out of the box,” Shaggy says. “At the time, we were in Britney and *NSYNC mode, and here comes this song that comes out of nowhere.”

Shaggy says he had to be confident in himself to release “It Wasn’t Me,” a song that he calls “unorthodox and against the grain.” Also, record companies were hesitant to put millions behind an artist with no track record at the time.

Two-and-a-half decades later, there are TikToks with Gen Zs dancing to the song, and another one of Shaggy’s hits, 1995’s “Boombastic,” was recently featured in a Fiat ad.

Now, Shaggy is on a mission to present a history of reggae that will bring him to the Heinz Hall stage to perform with the Pittsburgh Symphony Orchestra. He first got the idea to tell this story with his music through an unlikely friendship with Sting (more on that later). After watching Sting’s 2023 performance at the same Pittsburgh venue, Shaggy was moved, and after speaking with Sting, was inspired to do his own show.

“When Sting did it, he did it with really just his catalog, but I wanted to use the platform to tell a story of Jamaican music,” Shaggy says. “Jamaican culture has been so influential in popular culture — look at everything Grace Jones did, or Lady Gaga or Doja Cat, or the biggest rock band in the world, U2, which was founded by Chris Blackwell, had some Jamaican reggae influence.”

Even Sting’s band, The Police, has reggae and Calypso influences.

Shaggy is planning to showcase a reggae anthology where he tells the backstory of how influential the music has been on popular culture. He also plans to tie it into his catalog of music, and the stories behind some of his songs, and how they’ve become a part of pop culture — like “It Wasn’t Me,” which has transcended multiple decades.

“There’s been a lot of negativities associated with reggae over the years,” he says. “A lot look at the music and culture as a homophobic culture with homophobic music, or it’s the music of guns and violence, or the music of weed.”

Shaggy encourages those who are interested to “not judge a book by its cover.” “A lot of things reggae is involved in are incredibly positive, and that is what I try to do, shed the light on their importance,” he says. “Reggae and dance hall music is a music of love, a music of fun, and a music of celebration; it’s also a music of protest — I want to bring audiences on that roller coaster of different things.”

In addition to his show in Pittsburgh on February 26, Shaggy is releasing a song with Sting later this month. Calling Sting the “bro he didn’t know he needed,” the two first met in Antwerp, Belgium in 2004 when Sting called him to the stage to perform “Roxanne” with him. Shaggy didn’t see Sting for years after until they had dressing rooms next to each other at an awards show. They spoke again a while later after Shaggy’s A&R (artists and repertoire) representative played Shaggy’s song “Don’t Make Me Wait” for Sting. Sting loved it, and the duo “ended up in the studio having more laughs than work,” Shaggy says.

The two collaborated on the Grammy winning 2018 album 44/876, touring the world together.

Sting’s wife, Trudy Styler, and Shaggy got along well, as did Shaggy’s wife, Rebecca, and Trudy. Their families vacation together and now, Sting and Shaggy speak every week, sometimes multiple times per week.

As far as his time in Pittsburgh, Shaggy is looking forward to having Primanti’s version of a cheesesteak.