The Lottery feat Shaggy
7/2/20261 hr 22 min
On this episode of The Almanac of Rap, Donwill sits down with Grammy Award-winning artist Shaggy for a wide-ranging conversation about building one of the most enduring careers in music, navigating the intersection of reggae and hip-hop.
From his early days recording "Oh Carolina" while serving in the U.S. Marines, to the global success of "Boombastic," "Angel," and "It Wasn't Me," Shaggy reflects on the moments that shaped his career and the mindset that helped him remain relevant for more than three decades. Shaggy breaks down:
Working with Michael Jackson, Sting, Spice, and Eddie Murphy
Dancehall's influence on hip-hop, and Jamaica's rich lyrical tradition
His new album Lottery, and starring in The Last Ship at New York's Metropolitan Opera.
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Clips
Transcript preview
First 90 secondsShaggy· Guest0:00
What you getting from Lottery is really a 2026 version of Shaggy.
Don Will· Host0:06
Yeah.
Shaggy· Guest0:06
Of Shaggy's music. You know what I'm saying? If you coming on there saying you gonna get some, some trend or something like that, that's not that. What you g- I, I think that's a mistake I see a lot of legacy artists do by trying to make new music. And you got a fan base that has been with me for 30 years, that have been rocking with me and filling, you know, venues with me, and then you're gonna do something that they're like, "Well, I can't even relate to this."
Don Will· Host0:30
Mm-hmm.
Shaggy· Guest0:30
So I literally try to create, um, subject matters that's relatable to people's lives, both young and old, right? But it's still Shaggy.
Don Will· Host0:41
Yeah.
Shaggy· Guest0:42
You know? And that's that, that, that Shaggy feel that you're gonna get. Like when I say dancehall, reggae, and Shaggy music, it's Shaggy.
Don Will· Host0:48
Right. And like, and, and I would imagine, not even imagine, at your shows now, you have parents and children together- Oh, yeah, yeah, yeah ... coming in.
Shaggy· Guest0:55
It's mixed.
Don Will· Host0:55
So, so you're speaking to multiple generations.
Shaggy· Guest0:57
Absolutely.
Don Will· Host0:57
So- So I can't get too explicit either.
Shaggy· Guest0:59
I can't get... You know what I mean?
Don Will· Host1:00
Exactly. Like, and you- Yeah ... that, that hybrid style of like, like- Yeah, then you, then- ... Shaggy music is important Yeah.
Shaggy· Guest1:05
Then you, you know, you alienate yourself from the money.
Don Will· Host1:06
How long- [laughs] Man, that heavy talk right there. [laughs] This, this is what I need to hear.
Shaggy· Guest1:11
Like, why you wanna do that?
Don Will· Host1:12
[laughs] Why you wanna do that?
Speaker 31:13
[laughs] Yo, it's the Almanac of Rap show. I got opinions and they all factual. No news, just information that you won't be able to use unless you're at a dinner party trying to impress who's in attendance with endless tidbits of nonsense. We're gonna have a good time,