Sitting on opposite sides of a plain, wood table, Sting and Shaggy are anything but ordinary.

Their 20-year friendship - unlikely on the surface, but quite fitting musically given Sting’s reggae leanings with The Police - has yielded joint tours, a Grammy-winning album (“44/876”), a curated festival and a volley of good-natured zingers.

Ask what they most appreciate about each other, and Sting, 73, lands first.

“Oh, where should I begin?,” he muses. “Let me count the ways.”

Shaggy, 56, hops in with a checklist of mutual interests. They’re both Libras. They share an affinity for Monkey 47 gin. They adore Bill Withers.

“We’re both obsessed with music and we love the element of surprise," says Shaggy. "What is so unique is we have different processes of how we achieve... I’m fascinated with his process and I think he is fascinated with mine.”

Cue a quizzical look from Sting.

“You have a process?” he deadpans.

Much laughter is shared as the pair chat from the Czech Republic in July, where they were playing (separately) at the Colours of Ostrava Festival.

They’ll unite again for their One Fine Day Festival, a two-stage, all-day event curated and headlined by the twosome. Joining them for the Sept. 6 production at The Mann in Fairmount Park in Philadelphia is an eclectic lineup featuring O.A.R., Marcia Griffiths, Chance Emerson, The Original Wailers featuring Al Anderson, Big Freedia and Sophie Grey.

This is the second installment of One Fine Day - named for a song about climate crisis on Sting’s “57th & 9th” album - which they also staged in Philadelphia in 2023. The festival is also a charity partner for St. Jude Children's Research Hospital.

For both artists, the element of surprise is integral to the festival, along with having a blast performing together.

Here’s more from the duo about their mutual admiration society, the endurance of Sting’s “Fragile” and why Shaggy loves hearing his music played by a symphony.  

Question: What do you appreciate about performing together?

Sting: I love his spontaneity. Shaggy is a very spontaneous performer and creator. I’m a lot more hidden in my book.

Shaggy: People expect him to be this really straight-laced guy and he’s super funny. We play off each other. We like each other and it feels good.

Who takes longer to get ready to go onstage?

Sting: He’s very vain. I just go on as I am because I’m perfect (laughs). I wear the same T-shirt every night because that shirt knows all the songs. I’m not going to give that up. (Looks at Shaggy) You have a different frock on every night and jewelry… it’s like going onstage with the Queen of England, God rest her soul.

Shaggy: Don’t let him fool you. He has a rack of clothes, they’re just all the same T-shirt (laughs).

What is your favorite song of each other’s to perform?

Sting: Mine is Shaggy’s wonderful morality play “It Wasn’t Me,” because as scabrous as it is, it has a moral to it.

Shaggy: That’s when he goes into that schoolteacher talk! But for me, “Fields of Gold.” It’s an incredible melody. The song is recorded with a certain mood. There are some songs you hear and some you feel, and that is one I feel.

With the festival, who curates the lineup and what are you looking to bring fans?

Sting: We want to surprise people. When we did it two years ago in Philly, he and I introduced every act and walked the audience from stage to stage. We genuinely curated the mood. We didn’t just sit in our dressing rooms waiting for our bit. We will be the gracious hosts.

Festivals are not easy to produce. Why do one in the first place?

Shaggy: It’s cool to do it where you’re hanging with your peers. I did it with Shaggy and Friends in Jamaica so I know how difficult it is. But if you’re gonna do it, have a partnership with Live Nation because this is what they do. It’s different in the U.S. with laws and regulations and permits and they take care of all of that.

Sting: We became aware that there was a niche in the marketplace that could be filled by us in Philly, which is a great music town, a great music audience.

And you will share the stage again?

Shaggy: We have two bands together and we just trade and he sings a couple of my songs and I do a couple of his.

Sting: We usually start with “Jamaican in New York,” which used to be “Englishman in New York,” but I got pushed out of the way. But I don’t mind.

Shaggy: Lately we’ve been having fun with “It’s Probably Me.”

Sting: I wrote that for Danny Glover and Mel Gibson in a “Lethal Weapon” movie. I’m the Danny Glover in this relationship.

Sting, “Fragile” has been getting some attention lately with its use in (Netflix series) “Adolescence” and you duet with Barbra Streisand on her new album. What is it about that song?

Sting: It was always my ambition to write standards; songs that would survive the test of time, that would be covered by other artists and I think “Fragile” has achieved that state over the years. It’s quite an old song (from 1987’s “Nothing Like the Sun” album). It has many meanings. What am I singing about? A relationship? The fragility of the planet? Of our democracy? Our ecosystem? It’s all of those rolled into one. And I love Barbra’s version of it.

Did you record in the room with her?

Sting: Yes! There I was on one side of the microphone and one of the greatest singers of our era is standing a few feet away from me. That’s something you don’t take for granted.

And Shaggy, you’ve performed with symphonies in Pittsburgh, Houston and San Diego. How do you feel hearing your songs presented so differently?

Shaggy: The first time I saw (contemporary music with a symphony) was when Sting did it (on his 2010 Symphonicity Tour). It sounded so great I thought, I’m gonna do that. For an artist who has been doing this for almost 30 years you look for different ways to be inspired and I’m not shying away from any of these things. Sting made me sing Frank Sinatra in reggae the other day. Who would have gotten me to do that?

Sting: Guilty!

(c) USA Today by Melissa Ruggieri