GRAMMY-winning dancehall reggae artist Shaggy recently participated in an installment of The Recording Academy's 5 Questions With … series. Held at The Academy's headquarters in Santa Monica, Calif., Shaggy discussed topics such as songwriting, musical influences, advice for young musicians, his service in the Marine Corps, and his latest album, Summer In Kingston.

"If my first four bars don't hold [your attention], then it's no good," said Shaggy regarding his songwriting philosophy. "If I don't get a reaction out of you from the minute the music starts, then I'm not onto something. That's my thought process. "

Born Orville Richard Burrell in Kingston, Jamaica, Shaggy was nicknamed after the "Scooby-Doo" character. After moving to New York in his late teens, Shaggy joined the Marine Corps and was stationed in North Carolina. During his service, Shaggy wrote and recorded music but his career was put on hold when he served a five-month tour of duty in Kuwait for Operation: Desert Storm in 1991. Upon his return, Shaggy resumed his music endeavors and recorded a cover of ska group the Folkes Brothers' "Oh Carolina." Shaggy subsequently landed a deal with Virgin Records and released his debut album, Pure Pleasure, in 1993. The title track to his sophomore effort, 1995's Boombastic, became his second UK chart-topper and shot to No. 3 on the Billboard Hot 100. The album also netted Shaggy his first GRAMMY for Best Reggae Album.

Hot Shot, Shaggy's fourth album, was released in 2000 and vaulted to No. 1 on the Billboard 200. The album spawned a pair of No. 1 hits, "Angel" and "It Wasn't Me," and has sold more than 6 million copies, an impressive crossover feat for a reggae artist. Shaggy has since scored three No. 1 albums on Billboard's Top Reggae Albums chart, Lucky Day (2002), Intoxication (2007) and Summer In Kingston (2011). In addition to music, Shaggy's philanthropic efforts include the Shaggy Make A Difference Foundation, which he established following a visit to Bustamante Hospital for Children in Kingston. In January 2009 Shaggy staged a benefit concert that raised $250,000, which was utilized to purchase medical equipment for the hospital.

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Updated Friday Oct. 13, 2023 to include info about Kendrick Lamar's most recent GRAMMY wins, as of the 2023 GRAMMYs.

A GRAMMY veteran these days, Kendrick Lamar has won 17 GRAMMYs and has received 47 GRAMMY nominations overall. A sizable chunk of his trophies came from the 58th annual GRAMMY Awards in 2016, when he walked away with five — including his first-ever win in the Best Rap Album category.

This installment of GRAMMY Rewind turns back the clock to 2016, revisiting Lamar's acceptance speech upon winning Best Rap Album for To Pimp A Butterfly. Though Lamar was alone on stage, he made it clear that he wouldn't be at the top of his game without the help of a broad support system. 

"First off, all glory to God, that's for sure," he said, kicking off a speech that went on to thank his parents, who he described as his "those who gave me the responsibility of knowing, of accepting the good with the bad."

Looking for more GRAMMYs news? The 2024 GRAMMY nominations are here!

He also extended his love and gratitude to his fiancée, Whitney Alford, and shouted out his Top Dawg Entertainment labelmates. Lamar specifically praised Top Dawg's CEO, Anthony Tiffith, for finding and developing raw talent that might not otherwise get the chance to pursue their musical dreams.

"We'd never forget that: Taking these kids out of the projects, out of Compton, and putting them right here on this stage, to be the best that they can be," Lamar — a Compton native himself — continued, leading into an impassioned conclusion spotlighting some of the cornerstone rap albums that came before To Pimp a Butterfly.

"Hip-hop. Ice Cube. This is for hip-hop," he said. "This is for Snoop Dogg, Doggystyle. This is for Illmatic, this is for Nas. We will live forever. Believe that."

To Pimp a Butterfly singles "Alright" and "These Walls" earned Lamar three more GRAMMYs that night, the former winning Best Rap Performance and Best Rap Song and the latter taking Best Rap/Sung Collaboration (the song features Bilal, Anna Wise and Thundercat). He also won Best Music Video for the remix of Taylor Swift's "Bad Blood." 

Lamar has since won Best Rap Album two more times, taking home the golden gramophone in 2018 for his blockbuster LP DAMN., and in 2023 for his bold fifth album, Mr. Morale & the Big Steppers.

Watch Lamar's full acceptance speech above, and check back at GRAMMY.com every Friday for more GRAMMY Rewind episodes. 

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As Jagged Edge and Nelly asked in 2001, where the party at? On May 6, it's at the Las Vegas Festival Grounds thanks to Lovers & Friends.

The star-studded festival largely celebrates the R&B and hip-hop stars of the '90s and 2000s, with a lineup that boasts Missy Elliott, Mariah Carey, Boyz II Men, Usher, Christina Aguilera, Nelly, and 50 Cent, among countless other hitmakers. With a jam-packed roster, it's hard to believe the fest is only one day. But one thing is guaranteed: it's going to be a day full of bangers.

There's also a good chance that there will be some viral moments from the second annual Lovers & Friends fest. Several of the stars on the bill have delivered some smash hits together, and they may just take the stage together to perform them — whether it's Chris Brown and Busta Rhymes for "Look At Me Now," Frankie J and Baby Bash for "Suga Suga," or, yes, even Jagged Edge and Nelly for "Where The Party At."

Even if you didn't get a ticket to this year's sold-out fest, that certainly doesn't mean you can't get in on the nostalgia. GRAMMY.com has curated a 50-song playlist to highlight all 50 performers on the Lovers & Friends 2023 lineup (which also includes current stars like Summer Walker, Bryson Tiller and Partynextdoor), and it will undoubtedly get you pumped up.

Below, jam out to GRAMMY.com's Lovers & Friends 2023 playlist, or listen to it on Apple Music, Amazon Music or Pandora.

"There’s no need for purist music," says reggae icon Shaggy, who brought this attitude to an unlikely source.

His latest album, Com Fly Wid Mi, runs Frank Sinatra songs through a filter of ska, swing, and reggae rhythms. On his second collaboration with producer Sting, Shaggy dropped his signature dancehall toasting voice in favor of a new croon, which floats through a range of Ol' Blue Eyes' tunes — from “Luck Be a Lady” to “Fly Me To The Moon." 

"Whatever we're doing has already been done by somebody, but it's the feel that you put in that makes it different," Shaggy tells GRAMMY.com. The pair's unique feel netted Com Fly Wid Mi Best Reggae Album nomination at the 2023 GRAMMYs.

Shaggy — born Orville Richard Burrell — has been making musical nods to his predecessors since 1993. That year, he released a high-energy dancehall version of “Oh Carolina,” a 1958 Folkes Brothers tune that was an early hit in the genre of ska, the precursor to reggae music. 

Since then, Shaggy has released more than a dozen albums, often featuring an eclectic range of samples — from Steve Miller Band's "The Joker" to Cyndi Lauper's “Girls Just Wanna Have Fun.” He frequently collaborates with artists like will.i.am, Maxi Priest, Spice, Chaka Khan, Sean Paul, and Barrington Levy. Shaggy’s music has won two GRAMMY Awards, a Brit Award and a Juno award; he received an honorary degree from Brown University and a Jamaican order of distinction.

From his home studio in Miami, where he's worked for many years, Shaggy spoke with Grammy.com about his love of reggae and how Sting helped him learn to appreciate his own voice. 

How are you? What have you been up to? 

I had a great year. We toured Europe and Australia, and had a really good time. I teamed up with Sting again to do crazy things and we released this album Com Fly Wid Mi. With this project, I didn't know what we were doing and how it would go. But we had a vision. 

But the year was also bittersweet because I lost [bass player and producer] Robbie Shakespeare of Sly and Robbie. He was a mentor of mine, like a father figure to me. We went to the funeral and that was rough. 

Shakespeare was one of the greatest musicians and also an amazing person. Humility is the biggest thing he taught me.  As a person from the ghetto, he helped me realize my purpose. He would say you're here as a servant to change people’s lives. 

Well you clearly listened. Don’t you think you’ve found your purpose?

In '93, when we did [a cover of the Folkes Brothers 1959 song] “Oh Carolina,” I was dubbed a one-hit wonder by British tabloids. I had flipped an old song and it went Top 5. It was the first time a dancehall song went to the top. 

They said I’d never get another one. They said you’ll never write your own hit. The next record I wrote, it had to be bigger, and I had to write it myself, so I wrote Boombastic” which won a GRAMMY [for Best Reggae Album at the 38th GRAMMY Awards]. So it was off to making history from that point on. 

Why did you and Sting decide to interpret Frank Sinatra songs in a reggae style? 

Look at artists like John Holt, who wrote “The Tide is High,” which Blondie covered. In his earlier days, he was super popular, and used to do a lot of older American pop songs and soul songs that became part of the Jamaican songbook. 

When I listened to [Jamaican radio station] Irie FM in the late '80s and early '90s, they played a lot of American music, as well as country music from Kenny Rogers and Dolly Parton. Songs by Bing Crosby, Nat "King" Cole, and Patti Page were played in my house, with chicken and rice and beans for Sunday dinner. Growing up as a young Jamaican, I heard that music a lot. It’s not by chance that Sting heard me singing Sinatra songs for fun. 

I became known for my signature dancehall voice from Boombastic, but with Sting in the studio, he heard my real voice. He said you can really sing, you’re not just a dancehall singer. He was in love with my voice and pushed me out of my comfort zone. I’m not really comfortable with my singing, but Sting is a great producer and my big brother, so if he says sing, I will sing, no matter how uncomfortable it is.

Why are you not comfortable with your singing?

I came up in dancehall, so my heroes are Josie Wales, Super Cat, and Shabba Ranks. Those guys are giants. In dancehall I was getting big hits, so I was comfortable only in playing that part, but if you're comfortable, you are stagnant, and Sting kept pushing me to be uncomfortable. 

What unique challenges and opportunities did you both experience turning Sinatra tunes into reggae songs? 

The main challenge is that it could easily get corny. Also, Sinatra songs are jazz tunes with five or six chord changes, but most cool reggae is just two chords, so we had to limit the changes to make it cool. So we had to figure out which chords to take out to make it reggae. It can’t be too jazz, or too reggae, so that was the balance. 

That’s where the genius of Sting came in. He knew what notes to take out but how to keep the melody that makes it work. That took effort. It's really cool to know I did something cool that nobody had done. 

**You’ve worked with Sting twice now, and your previous collaboration with Sting, 44/876,  also won a Best Reggae Album GRAMMY Award. How is your work with Sting different from other projects you’ve done?**

This is an unlikely pairing. We’re from two different eras, and he’s a giant. We have a good f—ing time bro. We tell jokes and we're laughing. 

He clearly knows way more about music than me, but admires me enough to work with me. In the studio, I’m throwing freestyle and gibberish. He said he had never done that; he’s usually by himself working quietly. He said he had never seen anyone write songs as quickly as me. I write about four songs a day.  I never paid attention to the instrumentation as much, but he taught me to pay attention and be a part of it. 

Sting said he watched [Aston] “Family Man” [Barrett] play with Bob Marley and tried to emulate him on bass, but couldn't do it. So he came up with a hybrid, and that became the sound of the Police. He and I agree, there’s no need for purist music. Whatever we're doing has already been done by somebody, but it's the feel that you put in that makes it different. There’s always a new story to be told. There’s records you hear, but then there’s records you feel. Like Bob Marley, when he sang, you felt it.

You turned Sinatra’s “Come Fly With Me” into a rocksteady/ska tune and "Oh Carolina"  was a remake of Prince Buster's  1960 ska tune. What’s your connection to the legacy of early reggae/ska/rock steady? 

My grandmother was a Christian woman, but she loved Toots and the Maytals, and those ska records were played in my home a lot. It’s ghetto music but fun music, and so danceable. 

Dude I make everything from what was made before. I’m not inspired by what is happening now. I’m always thinking, how can we take what was done then and make it unique and cool now?  Three days ago I was listening to “Guns of Navarone” by the Skatalites, and wondering how can I use this? I pull a lot of my inspiration from that old stuff.

You’ve won many awards and accolades. Which one feels most special to you? 

I’m proud of the JUNO [Canadian Music Award] because I was the only international act to get one. But anyone who gets a GRAMMY is happy. 

And here we are again. I’ve been a changer of this reggae genre through and through. I step outside the box, that’s the only way the genre will grow. I take changes, I step out.

Reggae music has gone through so many changes and iterations since its origins in the late 1960s in Jamaica. What do you think is the core element of reggae that gives it such staying power?

Reggae is the first and last music; so many genres have come from it. Reggaeton started from Puerto Rico. It was Spanish reggae, and the Latin community grabbed onto it and it became massive. Look at hip-hop. Kool Herc took Jamaican toasting and put it over R&B beats. When I go to Africa, they play dancehall in the clubs, not Fela Kuti. 

The impact Jamaican culture has had on the global culture is incredible. I am blessed to be a reggae artist. Reggae is not an art form, it's a lifestyle. I get up every day and this is what I’m doing. I don’t want to do anything else. Bruh, I work for the rewards, not the awards. I’m so fortunate. I would do this for free.

What made you want to sing in the first place? 

I learned the tone of my voice in the military by singing cadences. I would do these comical cadencies, so they called me out to sing them all the time and it made people laugh. It was hard because we did four or five miles at a time, so that was a lot of singing. 

I had no lessons, never had a vocal coach. I started on sound systems and perfected my craft by hanging with great singers like Barrington Levy. The closest I came to real training was with Sting. Anything theoretical was done through Sting. 

You’ve been mentored by Sting and Jamaican artists like Robbie Shakespeare, but now you’re also a mentor to younger musicians. How does that make you feel?

After a while life comes to you with a pursuit. James Brown told me once in my dressing room that they can take away your wife and your house, but not your talent. I believed him.

None of those accolades I can take with me, but I can inspire, and change someone’s family. I’m the only musician in my family, and now I have a niece at Princeton. We have changed the cycle of our lives, and that moves me, that excites me.

How has life during the pandemic been for you? Have you stayed busy or have you been taking it easy?

I worked throughout the whole thing. Now I’m excited about production projects with young writers and musicians. I’m like a kid in a candy store. Everybody keeps asking for a Shaggy record. But when Sting says let's go now, you go now! So we did the Sinatra album. It's like I'm his little project. But I’m overdue for a Shaggy record.

Will your new record come out in 2023?

I’ve been working on my latest record for the last three years. I have about 100 songs, and keep redoing it. I get inspired over and over again with new stuff. The hardest part is taking stuff out. 

Every record from my career has been done in the basement of my house, and I’m still in my basement. I’m still that guy, down with my crew and my team and f—ing with shit, and having fun. 

Whatever I do next won’t be what’s expected. If I do what's expected, then I’ve failed. I’m always looking for that new sound. I make records selfishly to please me. I don’t want to be bored, I’m allergic to boredom. If I'm not bored, then the record is timeless. 

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Updated Monday, May 22, to include information about the re-air date for "Homeward Bound: A GRAMMY Salute To The Songs Of Paul Simon."

"Homeward Bound: A GRAMMY Salute To The Songs Of Paul Simon" will re-air on Wednesday, May 31, at 9 p.m. ET/PT on the CBS Television Network, and will be available to stream live and on demand on Paramount+.

Many tribute shows for legacy artists end in a plume of confetti and a feel-good singalong. But not Paul Simon's.

At the end of the songbook-spanning "Homeward Bound: A GRAMMY Tribute To Paul Simon," the only person on the darkened stage was the man of the hour. Sure, the audience had been baby-driven through the Simon and Garfunkel years, into the solo wilderness, through Graceland, and so forth. But all these roads led to darkness.

Because Simon then played the song that he wrote alone, in a bathroom, after JFK was shot.

It doesn't matter that Simon always ends gigs with "The Sound of Silence." After this commensurately cuddly and incisive tribute show, it was bracing to watch him render his entire career an ouroboros. 

That "The Sound of Silence" felt like such a fitting cap to a night of jubilation speaks to Simon's multitudes. The Jonas Brothers coolly gliding through "50 Ways to Leave Your Lover," juxtaposed with the ache of Garth Brooks and Trisha Yearwood's "The Boxer," rubbing up against Dave Matthews getting goofy and kinetic with "You Can Call Me Al," and so on and so forth.

The intoxicating jumble of emotions onstage at "Homeward Bound: A GRAMMY Tribute To Paul Simon" did justice to his songbook's emotional landscape — sometimes smooth, other times turbulent, defined by distance and longing as much as intimacy and fraternity.

Here were eight highlights from the telecast — which will re-air on Wednesday, May 31, at 9 p.m. ET/PT on the CBS Television Network, and will be available to stream live and on demand on Paramount+.

Read More: Watch Jonas Brothers, Brad Paisley, Billy Porter, Shaggy & More Discuss The Legacy And Impact Of Paul Simon Backstage At "Homeward Bound: A GRAMMY Salute To Paul Simon"

Woody Harrelson's Lovably Bumbling Speech

After Brad Paisley's rollicking opening with "Kodachrome," the momentum cheekily ground to a halt as Harrelson dove into a rambling, weirdly moving monologue.

"The songs of Paul Simon really are like old friends," the cowboy-hatted "The Hunger Games" star remarked, interpolating one of his song titles and crooning the opening verse.

Harrelson went on to recount a melancholic story from college, where the spiritually unmoored future star clung to Simon songs like a liferaft. We can all relate, Woody.

Garth Brooks & Trisha Yearwood's Pitch-Perfect "The Boxer"

Brooks has always been one of the most humble megastars in the business, praising his wife Trisha Yearwood — and his forebears — a country mile more than his own. (Speaking to GRAMMY.com, he described being "married to somebody 10 times more talented than you.")

The crack ensemble could have made "The Boxer" into a spectacle and gotten away with it, but Brooks wisely demurred.

Instead, the pair stripped down the proceedings to guitar and two voices; Brooks provided an aching counterpoint to Yearwood.

Billy Porter's Heart-Rending "Loves Me Like A Rock"

The "Pose" star blew the roof off of Joni Mitchell's MusiCares Person Of The Year gala in 2022 with "Both Sides Now," so it was clear he would bring napalm for a Simon party. 

Given the gospel-ish intro, one would think he was about to destroy the universe with "Bridge Over Troubled Water." 

Instead, he picked a song of tremendous personal significance, "Loves Me Like a Rock," and dedicated it to his mother. The universe: destroyed anyway.

Stevie Wonder & Ledisi's "Bridge Over Troubled Water"

The question remained: who would get dibs on the still-astonishing "Bridge Over Troubled Water"? A song of that magnitude is not to be treated lightly.

So the producers gave it to generational genius Wonder, who'd bridged numberless troubled waters with socially conscious masterpieces like Songs in the Key of Life.

But he wouldn't do it alone: R&B great Ledisi brought the vocal pyrotechnics, imbuing "Bridge Over Troubled Water" with the grandiosity it needed to take off.

Jimmy Cliff & Shaggy Brought Jamaican Vibes With "Mother & Child Reunion"

Simon embraced the sounds of South Africa with his 1986 blockbuster Graceland, yet his island connection is criminally underdiscussed; since the '60s, Jamaican artists have enthusiastically covered his songs.

For instance, it's impossible to imagine a "Mother and Child Reunion" not recorded in Kingston, pulsing with the energy of Simon's surroundings.

Enter genre luminaries Jimmy Cliff and Shaggy, who flipped the tribute into a bona fide reggae party.

Take 6 Dug Deep With "Homeless"

Leave it to the Recording Academy to avoid superficiality in these events: Mitchell's aforementioned MusiCares tribute included beyond-deep cuts like "Urge for Going" and "If." 

Most remember "Homeless" as Ladysmith Black Mambazo unaccompanied vocal cooldown after bangers like "You Can Call Me Al"; eight-time GRAMMY-winning vocal group Take 6 did a radiant, affectionate rendition.

When Simon took the stage at the end of the night, he was visibly blown away. Touchingly, he shouted out his late guitarist, Joseph Shabalala, who founded Ladysmith Black Mambazo.

"Imagine a guy born in Ladysmith, South Africa, [who] writes a song in Zulu and it's sung here by an American group, singing his words in his language," Simon remarked. "It would have brought tears to his eyes."

Angélique Kidjo & Dave Matthews' Love Letter To Africa

Graceland was Simon's commercial zenith, so it was only appropriate that it be the energetic apogee of this tribute show.

Doubly so, that this section be helmed by two African artists: Angélique Kidjo, hailing from Benin, and Dave Matthews, born in Johannesburg.

"Under African Skies," which Simon originally sang with Linda Ronstadt is a natural choice — not only simply as a regional ode, but due to its still-evocative melody and poeticism.

"This is the story of how we begin to remember/ This is the powerful pulsing of love in the vein" drew new power from Kidjo's lungs. 

Afterward, Matthews — a quintessential ham — threw his whole body into Simon's wonderful, strange hit, "You Can Call Me Al."

The Master Himself Took The Stage

With his still-gleaming tenor and still-undersung acoustic guitar mastery, Simon brought the night home with "Graceland," a Rhiannon Giddens-assisted "American Tune" and "The Sound of Silence."

At 81, Simon remains a magnetic performer; even though this is something of a stock sequence for when he plays brief one-off sets, it's simply a pleasure to watch the master work.

Then, the sobering conclusion: "Hello darkness, my old friend," Simon sang, stark and weary. With the world's usual litany of darknesses raging outside, he remains the best shepherd through nightmares we've got.

And as the audience beheld Simon, they seemed to silently say: Talk with us again.

15 Essential Tracks By Paul Simon: In A Burst Of Glory, Sound Becomes A Song