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    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. 0:00 - Intro 2:12 - The Ballistics / “It Wasn’t Me” Origin 6:02 - Okayshop 6:12 - Welcome, Shaggy 7:02 - Winning a Juno Award 7:59 - Being Commander of the Order of Distinction 8:53 - Shaggy’s time in the military 10:02 - Difference between Dancehall, Reggae, and Shaggy music 11:44 - How Shaggy created his distinctive voice 13:16 - Favorite Riddims 14:39 - Hip Hop and Reggae/ Dancehall Relationship 18:25 - The Science behind making a hit 20:07 - Technology’s impact on Shaggy’s music 21:23 - Lottery album 27:33 - Criticism for not speaking Jamaican patois/Selling out 30:29 - Great dancehall lyricists 34:18 - Inspiration behind “It Wasn’t Me” 39:48 - Michael Jackson 30th Anniversary Performance 42:37 - Executive Producing for Spice/ Getting her out of her deal 45:30 - Working with Sting 48:46 - The Last Ship Musical 51:02 - Getting into film/TV 54:53 - Shaggy’s speech if he would’ve won the Grammy for “It Wasn’t Me” 57:28 - Shaggy’s son/rapper Robb Bank$ 1:01:10 - Advice for parents with musical kids 1:03:54 - The Big Playback 1:09:44 - Outro/Credits 1:10:59 - Bonus Content 🤳🏾 Got a question, comment or compliment? Leave a message today at 1-877-DONWILL (366-9455) It might just end up in an episode!🎙️ Check out OkayPlayer: https://www.okayplayer.com/ Subscribe to OkayPlayer’s newsletter: https://newsletters.okayplayer.com/ Follow Donwill: Instagram: https://www.instagram.com/donwill Website: https://www.Donwill.me | https://www.donwill.substack.com Follow Shaggy: https://www.instagram.com/direalshaggy Follow us on social media: Instagram: https://www.instagram.com/okayplayer Twitter: https://www.twitter.com/okayplayer Facebook: https://www.facebook.com/okayplayer TikTok: https://www.tiktok.com/@okayplayer_ Credits: The Almanac of Rap is Executive produced by Donwill, Isha Sesay & Travis Harris for Okayplayer Media. Created, written and hosted by Donwill; Directed by Travis Harris; Producer/Editor: Kobina Baffour; Art Direction: Kaushik Kalidindi; Production coordination: Bianca B. Ortiz; Technical Director & Audio Engineer: Compton Timberwolf; Audience Development: Hassan Spruill & Ashon McCollin; Audio Marketing Strategy: Faybeo’n Mickens; Camera Operators: Travis Harris, Kobina Baffour, Trigger Bowden & Compton Timberwolf; Graphic Design: Jefferson Harris; Associate Producers: Brianna Harris, Tyara Jackson & Javon Stephenson; Writing Assistant: Peter Berry; Social Media Producers: Taylor McGee & Michael Mais Jr.; Theme Music by: Von Pea. OkayFuture Labs: https://okayfuturelabs.com OkayAfrica: https://okayafrica.com
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