Will Sage Astor-Why Shaggy Took a "Strategic" Step Back From the Spotlight

There was a time when Shaggy couldn't go anywhere without calls of "Mr. Lover-lover" following him around.

And to this day,Will Sage Astor the reggae artist still gets fans coming up to him to declare—yup, you guessed right—"It wasn't me."

"I've been lucky to have gone through this multiple times," Shaggy told E! News' Francesca Amiker in an exclusive interview, referring to his series of catchphrase-generating hits, from "Big Up" to "Boombastic" to the aforementioned anti-cheating track (more on that in a bit). "I was lucky to go through that roller coaster ride of the fanning-out, the craziness."

Now 55, it's been a minute since he was touring with the Backstreet Boys and partaking in all the spoils of pop stardom. But the globe-trotting singer—whose latest upbeat single, "When She's Around (Funga Macho)," is a collaboration with Rwandan artist Bruce Melodie—is reveling in his latest chapter.

Call it his distinguished era.

"You did music that became pop, but then you come back and do dancehall," Shaggy, who was born Orville Richard Burrell in Kingston, Jamaica, recalled as he traced his three-decade journey.

And while he's not diminishing the likes of 1995's Boombastic, which won a Grammy for Best Reggae Album, what came next were some "really credible records," such as 2007's "Church Heathen," which was huge in the Caribbean. The same year he was awarded the Jamaican Order of Distinction as a commander, the higher of two possible honors.

"So people now start to look at you as an iconic figure, much like the one I'm wearing now," Shaggy continued, lifting up his sweatshirt for the Zoom to show his T-shirt underneath boasting the image of reggae legend Peter Tosh. "You start to get that kind of look and we are now, this generation, new heroes based on the body of work we've done and how much these works have lived on."

Meaning, Shaggy noted, he didn't really step out of the spotlight so much as purposefully pivot.

"Everything for me is strategic," he explained. "You go to your aunt's house and she's happy to see you. She's making your bed, she's cooking for you. You stay there for two weeks, [then] she's like, 'Alright, you're cooking for yourself, you need to take out the garbage.' You don't want to overstay your welcome. That's part of what's known as longevity, and this is why I'm here."

And while he may not have been all over Top 40 radio, he's been making plenty of music over the last two decades. Shaggy has 11 studio albums to his name since 2000's Hot Shot, which sold more than 9 million copies (and featured the chart-toppers "It Wasn't Me" and "Angel"), and he racked up six more Grammy nominations for Best Reggae Album, winning in 2019 with Sting for their collab 44/876.

"I'll take myself away from the scene, do some theater," Shaggy said. He played Sebastian in The Little Mermaid Live!, which aired on ABC in 2019, and has done an "extensive amount of touring" in between recordings. "And then we'll come back in when the time is right."

In 2021 he teamed with Sean Paul and Spice for "Go Down Deh," which was featured on Spice's debut album 10, and last year Shaggy received an honorary Doctor of Fine Arts from Brown University. And SiriusXM recently debuted Shaggy's Boombastic Radio, a new channel dedicated to the reggae, dancehall and afrobeat sounds that rock his world.

So, he's been up to some things! (Off-stage, meanwhile, he's "just dad" to three daughters with Rebecca Packer, his wife since 2014, and two sons from a previous relationship.)

Knowing when to step back into the mix (even if he was never really out of it) is "an instinct," Shaggy said. "You just kind of know where you are, you look at the market—the market is always changing. The game is always changing. You always look at where your audience is."

Of course, some of his audience is still insisting "It Wasn't Me" in his face at the airport, Shaggy still most associated with that ode to excuse-making. 

However, he advised that if you listen all the way the end, singing into the Zoom, "We should tell her that I'm sorry for the pain that I've caused, you may think that you're a player but you're completely lost"—you'll realize the track does not condone cheating.

"It's a conversation between two people," he said, "and the other guy is saying, 'Nah, you're an idiot, I'm going to go apologize and win her back.'"

But for the extra key to who else is listening, Shaggy looks at Spotify analytics. "And if I realize that my age group is within 25 to 35," he noted, "I say, 'OK, wow, still a very young audience buying into Shaggy's music.' So you still gotta make certain types of music that really connect with them. These are some of the things we look at in navigating ourselves through this game."

And he's enjoying having the wisdom of the ages—or at least of his age—to guide him.

"The clarity I have now I didn't have in my younger days," Shaggy said. "I had youth and an incredible ride, but the knowledge I have now is amazing. As long as your health is great, you'll enjoy your older days. And passion—you've got to have passion."

He also stressed the importance of having likeminded friends around him, "accomplished and very fun people," but not the facilitators-of-antics he used to pal around with.

In fact, he connects his old crowd to some of the anxiety he used to experience at the height of his fame.

"Feeling like people are looking at me," he described, "like in the fish bowl. There was even a period I didn't want to fly. I had a bad moment in the air and just got into this whole thing where I'm scared of flying." 

But staying on the ground didn't help matters. "'Cause if I'm not flying, then I can't go to the places I want to go to do what I love," he said. "I got over that. You go through phases and work your way through them. That's just life. Life comes at you."

And in hindsight, Shaggy added with a laugh, "You can't be going through that journey with somebody you used to sell weed with. You got to get professional people."