Usher at the Crossroads

by Dan Piepenbring

After three decades in the limelight the R&B superstar is exploring new avenues

I’m reclining on a leather couch with Scarlett’s tongue in my mouth. Scarlett is Usher’s dog, a Goldendoodle with a lustrous, coppery coat and a probing nose. The singer donated $12,000 to take her home after a charity auction a few years ago, which makes her easily the most deluxe animal ever to lick me—my own net worth seems to rise by affiliation. Her affections so disarm me that I don’t notice Usher descending the stairs.

“Come here, Scarlett, come here,” he says. “Sit, sit.”

Once Scarlett’s settled, Usher joins me on the couch. We’re in his suite at the Greenwich Hotel, which boasts enormous slanted windows, a stone fireplace, and an abundance of wood paneling. He inhabits it lightly: cologne in the air, a white coat slung over a chair, a bowl of lemons on the counter.

“I’m in a very expressive place,” he tells me. “My priorities have changed.” At 37, Usher speaks with the easy confidence of one who’s grown up in the public eye. He’s charmingly aware of this: just when his conversation feels polished to a high shine, he likes to run it through the mud a little bit, finishing a thoughtful, articulate paragraph with a fusillade of expletives. At his most emphatic, he punctuates his sentences with a soft clap. “It’s not about attaining success. That’s not it. I’ve done that shit. And I’d like more of it, don’t get me wrong, but it’s really about being connected to what you’re doing. And not making it so deep that people don’t understand it, having fucking fun and enjoying it.”

He rests his chin in his hand. “We can choose to live and learn or we can just continue to preoccupy ourselves with distractions and repetitive sorrow. It could be that I’m getting a little older—I have a responsibility to teach my kids and just to know who I am.”

Today he’s dressed in all black down to his fringed sneakers, which are freckled in a blue-green pattern reminiscent of a coral reef. He has a meticulously groomed beard and eyes that amplify his broad smile. Around his neck he wears a glittering gold pouch that looks to me like a luxury hand-grenade. It’s filled with crystals—a creation of his wife’s, he tells me, designed to harness various energies. “I change the crystals out. Sometimes I wear amethysts.” As if reading my mind about the grenade thing, he adds: “There are many different things we can arm ourselves with.”

Usher has enjoyed such success that he needn’t arm himself with anything; many in his position would be content to rest on their laurels. But he’s pushed himself toward an enviable crisis of identity: he still has the vocal talents and the smooth, slightly rakish sex appeal that brought him to prominence in the ’90s, but he’s also a husband, a father of two, and a philanthropist. On his Snapchat, you might find him tearing a new Ducati through the night or enjoying a contemplative moment in the steam room, his abs on display, his junk tastefully concealed by an oversized emoji. But in private Usher is researching the Yoruba Diaspora. He practices Transcendental Meditation. He collects art: Chris Cooksey, Richard Colman, Romare Bearden, Gordon Parks, and Daniel Arsham: whose sculptures in ash and obsidian feel attuned to Usher’s persona. And he reads: Ta-Nehisi Coates’s Between the World and Me (2015) and Adam Hochschild’s King Leopold’s Ghost (1998), an excoriating history of Belgian colonialism in the Congo.

All of that provides him with what he calls “another gear.” “I look at artists like Marc Quinn, out of London,” he tells me, “who finds ways of being controversial that are actually direct.” Usher has sought that directness in his work, most notably in the music video for “Chains,” which shows images of police brutality victims. If ever the viewer allows his eyes to wander, the video pauses with a stern message: “Don’t look away.” Whereas many artists face the longueurs of middle age by churning out derivative pablum, Usher’s singles in recent years—especially “Climax,” “Good Kisser,” and “I Don’t Mind”—are the most nuanced and idiosyncratic in his catalog. With his career well into its third decade, Usher is neither the Next Big Thing nor the wizened elder statesman, already twinkling in the pop firmament. So... who is he, and why?

He’s been asking himself those same questions, though you’ll never meet anyone facing an existential dilemma with greater reserves of calm. “I always felt like there was a disconnect to me as an African American,” he tells me, noting that he’s been researching his bloodline. “I know that I’m from the South, but if I go deeper, where am I from? Who am I? I know that obviously I’m part of the diaspora descended of Africa, but where am I from?”

Those questions were implicit in the title of his last record, 2012’s Looking 4 Myself; leaning forward and clasping his hands, he assures me that his new album continues the search. “It’s about my musical journey through genre... The man I’ve become, the experiences and the vulnerability, the honesty, the inquisitive nature of who we are as people, as men—I’m talking about that. And the idea of the diaspora. There’s something amazing and undeniable about the culture of the South. The way we move. And where does it come from? When I look at how Africans move, how their rituals went and what their tribal moves were, and then I look at how we move now, there’s a tie.” He does an impressive simulation of an 808 kick drum: “that ties to Africa, Afro-Cuban music, Afro-rock music, right?”

The mention of Cuba evokes memories of his recent travels there. Along with Smokey Robinson and Dave Matthews, Usher was part of a 33-person delegation sent by the U.S. government—the state’s only official foray into Cuban culture since the rapprochement. “We were just in the street, with the people,” he says. “And a lot of the time American artists don’t really get to feel the people.”

Imbibing as much of the culture as he could, he met a raft of Cuban artists. He takes out his phone to show me a work by Sandra Pérez, who he’s especially moved by. “There’s this one immersive piece that I love that she does. You’re looking in the mirror, and on one side there’s messaging of all the negative things you could potentially be, and on the other side there’s the same messaging but positive. The entire exhibit is you just standing there in this space listening to these different images and ideas of who you are.”

Usher plans to return to Cuba as often as possible. On a previous trip with Ludacris, he toured the Cohiba Cigar Factory, where laborers dry tobacco leaves on their thighs. And he’s sampled the nightlife: “I had a few—or more than enough—mojitos.”

But his trip home in April came with devastating news: Prince had just died. “I remember just sitting in my seat—I think I held the plane up, because everyone had departed, but I was so broken up,” he says. “We’re losing our icons and we’re not taking the time to appreciate them enough while they’re alive. It’s only in the time of departure that we begin to understand the importance of who they are, what they represent. Prince has one of the most enticing relationships between religion and sexuality. When you listen to his music and you begin to understand all the places he pulled his references from, it’s just amazing, man. There’ll never be another Prince.”

It gets him ruminating on the conventionality of the music industry. “If something works, we tend to go toward it and stay there. I actually try my hardest to push the limit, but looking at the culture of music and where it is, it’s just like, ‘damn,’ is it okay to be unique anymore? The more unique you are, the better you are, right? Okay, but that’s not as gratifying and not as rewarding, because you don’t get the accolade and the hit right away.” He claps once, as if he’s about to issue an edict: “If you’re able to find that delicate blend of your identity and also do something everyone can relate to, then bless you. But it’s hard.”

As Scarlett trots over for a quick nuzzle, Usher turns his attention to his other passion of late: acting. It affords him a rare chance to step outside himself. “When I’m preparing for a character—my homework, I love it. I love the research. I’m willing to do the work.” So much so that he decides to break the fourth wall with an appeal: “If you reading this shit right now and you thinking about booking me for a movie, do it, because I’m muthafuckin’ worthwhile.”

You can see firsthand in August, when his new movie Hands of Stone arrives in theaters. His role as Sugar Ray Leonard is his largest to date, and he did do the work—practically method acting. “I had to think and eat and drink and move and run every morning and all of the things that you have to do as a boxer. I had to weigh in. I had to go through the process of losing the weight. I wanted to completely understand what it felt like to go through that stress. His eyes. The way he kind of maneuvers through the first and second fights [against Roberto Durán, played by fellow Flaunt cover star Edgar Ramirez], who he was. There was an awakening in the boxer and the person, for Sugar Ray, that people never got a chance to see. A vulnerability. We know him as the all-American with that boyish smile. I wanted to show the other side.”

He was proud of his performance, but he wouldn’t accept that he’d done a good job without Sugar Ray’s imprimatur. He got it—but it took some doing. “I was sweating bullets,” he says, “waiting by the phone for him to call me back. Call Harvey Weinstein, he’ll tell you. I beat him down, like, Did he see the movie? Get him the movie, get him the movie, did he get the movie, did you call him, call him back, did you call him, he didn’t get it, call him again, please call him, call him back, I just talked to him, call him again—”

There’s a knock at the door. Usher is late for rehearsal. He’s preparing for a few shows with The Roots—the first time he’s ever been backed by them. “Bands like that—you know, you make a quick sign in the air and everyone moves in sync? You saw bands like that in the sixties,” he says. His live shows, he adds, “have become very impromptu, not as rigid. It’s reminiscent of Africa, of Fela Kuti, of James Brown. Their style was a matter of accumulating all of these different experiences. Fela in America, James Brown in Louisiana, bringing those little nuances in and pushing the envelope.” He leaps to his feet and sings the first line of “Bad Girl” in that satin falsetto: “What y’all know about a / supermodel...” Scarlett offers a bark of encouragement.

Later that night, I catch his surprise show at Brooklyn Bowl. The room accommodates only a few hundred people, and the crush of the crowd, combined with the after-midnight start time, makes it an unusually intimate performance; Usher, peacocking in a Paradise Tokyo varsity jacket, is clearly enjoying himself. As well he should be: the band—more than a dozen strong, with a brass section and three backing vocalists—is in rare form. They open with a version of “Caught Up” spun through the James Brown soul machine, with Usher calling out hits and turnarounds on a dime. “Bad Girl” runs into a cover of Ramsey Lewis’s “Sun Goddess”; “Nice and Slow” breaks down into a quick tease of Prince’s “Adore.”

The blend of careful rehearsal and off-the-cuff theatrics puts me in mind of something he said earlier: “I do feel like there’s been a bit of a departure for me. I made a lot of moves in my past that I’m not so proud of... we all have to grow. You can’t continue to do the same thing and expect a different outcome. That might mean changing your circle, your perspective. But then knowing your way back home, understanding the path that leads you back to the foundation of who you are. And you carry all the things you learned on your journey...” His eyes widen and that self-aware smile creeps onto his face. “That’s a fuckin’ deep way of saying it. The layman fucking would just say I went through a lot of shit, and I talked about it.”

Photographer: Zackery Michael

Stylist: Jimi Urquiaga

Hair: Curtis

Makeup: Sacha Harford for V76 by Vaughn and Cover FX

Location: Sleep No More, NYC