By Raisa Bruner
December 18, 2019

Jason Derulo is disappointed in himself. This morning, after waking up at 5:30 a.m., he couldn’t find his sneakers. And then he had to find the gym. By the time he arrived for his workout, he only had 35 minutes left before his day’s appointments would begin—Sirius Radio, Jimmy Fallon, James Corden. Usually he can power through 100 push-ups in 10 minutes, but today he only hit 80. And for one of the world’s top-selling pop artists—and, now, an actor with a breakthrough role in the live-action movie musical Cats—that just isn’t good enough. “Gotta get right,” he complains, shaking his head.

Derulo knows this because he’s been putting in the work to make it in showbiz for his entire life. He notched his first big hit in 2009 with his moody pop-R&B debut single “Whatcha Say,” but he knew he wanted to be a performer at the tender age of four, after discovering Michael Jackson. And now he’s here: in a suite at New York’s opulent Plaza Hotel, just a few hours before the world premiere of the star-studded Cats. His eyes gleam almost as much as the glittering diamond choker around his neck; it’s been a good week for Derulo. He has been basking in the viral attention he’s received after a picture he shared on Instagram of himself in his underwear was removed for violating the platform’s Community Guidelines, prompting the hashtag #BringBackAnaconda. While making the rounds to promote Cats, he also spoke on the same theme when discussing the editing process for the “digital fur technology,” a topic that commanded widespread attention when the first trailer dropped this summer.

It’s all been rather R-rated. So how did one of pop’s sexiest voices, best known for club-favorite songs like “Wiggle” and “Talk Dirty,” end up in a PG movie musical helmed by the Les Misérables and The King’s Speech director Tom Hooper, based on the legendary Broadway show by Andrew Lloyd Webber, and co-starring the likes of Judi Dench, Ian McKellen, Taylor Swift, Jennifer Hudson, Idris Elba, James Corden and Rebel Wilson?

The cast of 'Cats' attends The World Premiere of Cats, presented by Universal Pictures in New York City on Dec 16, 2019.
Kevin Mazur—Universal Pictures/Getty Images

As it turns out, Derulo has always been a bit of a musical theater nerd. “Pretty early on, I started going to performing arts schools,” he explains. “I learned everything to be the consummate performer: every genre of dance, of music, mostly classical.” In middle school, he recalls, he walked by a room filled with “kids in costumes singing and dancing—and I thought, wait a minute, why the f-ck am I not doing this too? So from then on I was acting, too.” He went to college for theater, at the behest of his mom. When his music career took off, the acting got sidelined. But he had been looking for the right introduction to the world of movies. “I wanted to find a legacy role,” he says. “I was getting scripts all the time—but nothing inspired me to make that jump. Until Cats.”

A word about Cats: as one of Broadway’s longest-running and highest-grossing productions of all time, its cult-favorite status is hard to explain. Based on a book of playful T.S. Eliot poems, it introduces a series of idiosyncratic feline characters, many of whom are competing at the annual “Jellicle Ball” to receive the honor of ascending to the “Heaviside Layer” and starting a new life. As a movie starring Derulo and the rest, it’s just as hard to parse, though not without its pleasures. At the film’s premiere on a rainy night at Lincoln Center’s Alice Tully Hall, an exhausted Hooper—he said he finished editing the movie just the day before its screening—suggested it was about “the perils of tribalism and the power of kindness.” It’s also, as the movie’s finale lays out, about the fact that cats are not dogs.

“Doing theater, you cannot escape [Cats],” Derulo explains. After hearing that Hooper—“one of the classiest directors out there”—was slated to direct, Derulo made quick work of getting cast: “I went in to read for it, met with him, did some improv, danced, sang. Later that day they told us they wanted us to be a part of it,” he recalls. When you see Derulo in his Rum Tum Tugger glory, it all makes sense: his rakish sense of fun and his physicality as a performer all come together to make him a crowd favorite. With his blingy fish-skeleton chain necklace and Rum Tum Tugger’s reputation as the “terrible” and “curious” cat who all the lady felines adore, Derulo gets to shine in a raucous song-and-dance number that sees him making good use of his vocal chops and slick dance moves. (At the premiere, his moments onscreen were met with audience applause.)

To prepare for the role, Derulo dug in to the Rum Tum Tuggers of yore; he says he’s watched “every Rum Tum Tugger that there ever was, from community theater to Broadway.” His approach: “Cat first—really f-cking going there as a cat first.” He, along with the rest of the cast, participated in the much-discussed “cat school” to perfect their animal mannerisms. He spent time alone practicing his feline moves in the mirror until he felt satisfied. One thing he didn’t manage to do, though, was become a fan of actual cats.

“I’ve done like four cat [photo] shoots,” he says. “They want to put me with cats for some reason. I’m like, this is the worst idea! I’ve got on a fly outfit and you’re gonna put me with these dirty cats right now? Nah!”

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He did, however, bond with his fellow human cats in the cast. “It was like a four-month summer camp with some of your favorite people,” he says of the experience filming in the U.K. “An insane group. So much weird sh-t.” Like what? “Like Rebel Wilson licking me all day long. All day. You just have to keep doing the scene. We’re cats. We’re sniffing each other. We were pretty much naked. Lycra. Just naked. So we got very close, to say the least.”

Derulo also became closer to Swift, who he’s known for years, and found time to pick the brain of Elba, who he considers “the premiere black actor right now,” about his craft—specifically in action movies, which is where Derulo would like to see himself next. Derulo, who directs his own music videos but would like to move into longer-form directing, also did his best to learn from the Oscar-winning Hooper.

But still. Why Cats? “It transports you to a different dimension,” Derulo says. The movie is set in a human-sized world, with the sets scaled up so that everything is seen from a cat’s perspective. “I hope it inspires young kids,” he adds. “It’s a musical that we’ve needed for a long time. It’s very dance-centric, with all sorts of genres. And different races; everyone can see themselves. It’s very inclusive.”

That said, don’t expect to see Derulo in another movie musical any time soon. “If I do another one, then I become that guy,” he jokes. Right now, he’s in the middle of a two-part album, aptly titled 2Sides; the first half, which featured collaborators like Stefflon Don and Ty Dolla $ign, was released in November, and the second half is due in early 2020. A lot has changed in the music industry since he snagged his first hit a decade ago. “I sold like 4 million regular singles, and then 4 million ringtones,” he remembers, a bit incredulously, about the pre-streaming era. Those kind of sales don’t happen anymore, though. So over the past decade, he’s diversified his portfolio: he’s an investor in fitness company Rumble Boxing, in the L.A. hotspot Catch, in real estate. He’s performed at big-budget weddings in distant resort locations. He says he has a total of 13 businesses, not all of which he can currently disclose details about.

In a way, Derulo is the ultimate expression of a nimble millennial celebrity; now 30, he’s adapted to the changing music industry and celebrity complex to meet his audiences on every front, from Instagram to his brand collaborations. “What I did was very different from what any black male artist has ever done,” he recalls of his early days. “There has never been a black male artist to come out as a pop artist; that was unheard of.” This is, of course, somewhat hyperbolic: his own initial source of inspiration, Michael Jackson, famously earned the moniker “King of Pop.”

But Derulo has a point. Artists are often unfairly categorized based on appearance, race or origin, although Derulo’s genre-blending music has allowed him to sidestep limiting labels like “urban” or “R&B.” By sticking to his sound—big, club-ready dance tunes with catchy melodies and memorable samples—he’s made mainstream hit after hit. He may be best known for his name-dropping tagline, but he actually hasn’t put a signature “Jason Derulo” in his music since 2014. Now a Derulo song is recognizable because it feels like a Derulo song. “I always try to keep people guessing,” he says, “because once I do something a lot of people tend to jump on that vibe, so I can’t stay on that vibe for too long.”

Later on the night of the premiere, at the afterparty, Derulo swans around Central Park’s iconic Tavern on the Green in a long red coat, flanked by his team as he obliges requests for fan photos. Waiters pass around Cats-branded champagne and mini lobster roll toasts; a DJ who goes by “Hesta Prynn” plays hip-hop, although no one is dancing and the marquee’s plastic roof has started to leak under the drumming of the rain. Derulo seems content to hang out, though. He’s the last celebrity to leave. And in the morning? Maybe he’ll hit those 100 pushups. As he reflected earlier in the day, “I think the greatest gift that we all have is time. I’ve just had a lot more time than the average person on my craft, and I was obsessed from the beginning.”

Clearly, anyone who took Derulo as a one-hit wonder, the guy with the singsong name and the abs, underestimated his staying power. “I wonder what people’s perspective of me now is. Do they think I’m happy as f-ck?” He smiles, flashing a hint of that Rum Tum Tugger coyness. “I’m happier than I’ve ever been.”

Write to Raisa Bruner at raisa.bruner@time.com.

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