Why Stars Like Usher Need Creative Directors to Own Las Vegas

It was two days before the opening of My Way, Usher’s new, rebooted Las Vegas residency, and creative director Simon Hammerstein still had an important puzzle to solve.

Like any artist who does a residency, Usher has a big catalog of hits to choose from — the trouble was choosing which one would end the show. In the afternoon, Hammerstein settled into an empty row of VIP seats toward the front of the Park MGM’s Dolby Live theater, next to production designer Paul Tate dePoo, who quietly argued for “Love in This Club.” “I feel like Vanna White trying to sell this pitch,” he said drolly, pulling the track up on his phone. “Can you just let go of that song?” Hammerstein said with mock desperation. Still, Hammerstein asked DJ Mars — a longtime Usher collaborator who would perform in a booth set up in the middle of the first floor — to try it out.

Hammerstein wasn’t sold, though. So Mars suggested “Good Love,” Usher’s recent summer collaboration with City Girls. “Mars just solved it!” Hammerstein exclaimed. Twenty minutes later, though, his enthusiasm had dimmed, and he returned to an earlier choice: Usher’s dancefloor hit “Yeah!”

Aakomon Jones, Usher’s personal overall creative director, slid onto a stool next to Hammerstein. “Aakomon, perfect timing!” said Hammerstein. “We’re having a fight.” He explained what he wanted: a song that would effectively take advantage of the 23 dancers, roller skaters and pole dancers onstage and feel like “the choreographic version of a high-five … and then end with lasers and walk out to more lasers.”

Mars cued up the track and the cast went through the motions of the number, grouping up to perform in unison the club moves Lil Jon calls out at the song’s end: the A-Town Stomp, the Muscle, the Rockaway. Everyone agreed. “All right,” Hammerstein declared, “we’ve got an ending.”

It would still be a long next 36 hours for Hammerstein, 44, who came up in the downtown New York theater scene and is best known for co-founding The Box, an intimate nightclub with vaudevillian, burlesque and other outré entertainments. (Yes, he is the grandson of Broadway lyricist Oscar Hammerstein II.) His current role required him to weigh in on a list of last-minute issues: fine-tuning the automated time codes that coordinate the action, cleaning up the staging for “this kind of skate ballet” and figuring out how to fit more “Ush Bucks” into Usher’s shoes so the singer could make it rain during a strip-club sequence. For the creative director of a pop star’s Las Vegas residency, though, this is just another day at the office.

Over the past decade, the Vegas artist residency has gone from a career death knell to a transformative flex for established artists like Usher, who have catalogs so stacked they can easily sustain a 90-minute show. The era of the new-school residency arguably began in 2013 with Britney Spears’ Piece of Me. “Britney coming in such a big way when she was still incredibly relevant — I knew at the time that she would open doors, that people would think: ‘Sh-t, well, Britney did it …’ ” recalls Baz Halpin, the show’s creative director, who now runs the production and design agency Silent House. Organized into discrete acts with distinctive visual themes, Piece of Me used huge props, multiple glam costume changes and impeccably staged and executed choreography to reestablish Spears as a great entertainer.

For the right artist, residencies are a creative and logistical dream because they offer the rare chance to perform regularly for a consistent audience without travel. “I’ve been on the road since I was 17, so it’ll be nice to be settled a little bit,” says Miranda Lambert, whose Velvet Rodeo opens at Planet Hollywood’s Zappos Theater in September. It allows artists to better connect with their fans because the theaters are smaller. (The biggest at a Vegas casino, the Dolby Live, is roughly 5,000 seats.) And it lets them reach a much wider audience than just superfans. According to Live Nation senior vp of Las Vegas residencies Amanda Moore-Saunders, each year 42 million tourists come to Vegas from all over the globe (“It’s not uncommon for our major residency on-sales to see sales to fans in 50-plus countries”), most for three nights, with just one entertainment ticket already booked and free evenings to fill.

Above all, a residency allows for a level of big-budget spectacle that arena tours can’t sustain: Creating a Vegas residency show usually costs between $2 million and $10 million. Without trucks or sets that need to fit in them, Katy Perry can decide to put a 20-foot-tall talking toilet and a singing poop puppet in her ongoing PLAY at Resorts World. But pulling off that kind of thing every night gets complicated. It requires someone who can present star artists’ wildest dreams within budgets funded partly by guarantees from promoters, while putting out logistical fires and listening to everyone from the artist’s mother to their manager.

It’s a rare skill set — and without a creative director who has it, the show literally can’t go on. “What everybody loves about it is you get to see the overall vision,” says Napoleon Dumo, who with his wife, Tabitha, makes up the veteran creative direction duo Nappytabs. (The pair oversaw Jennifer Lopez’s 2016 All I Am residency.) “What they find out is it’s about a lot more than having a vision — and that’s the hardest part of the job.” Or as Halpin, who executive-produces Perry’s PLAY, puts it: “Ideas are like arseholes: Everybody’s got them. But you’ve got to have a structure and a plan. This is show business, after all.”

Even in the small community of Vegas creative directors, Hammerstein stands out. He’s not a choreographer (like ­Nappytabs) or a lighting designer (like Halpin) or an established longtime collaborator of an artist (like Rob English, creative director of John Legend’s Love in Las Vegas, or Ashley Evans and Antony Ginandjar of PLAY).

“It was a bold choice to go with someone more theatrical in background,” says Live Nation Las Vegas president Kurt Melien. (The company promotes My Way.) But for Usher, it was an intentional one: He was a longtime fan of The Box and loved how its atmosphere blurred the line between audience and performer. “How do you take the best of immersive theater and make it work for an audience who may not have seen it before?” Usher says. “That was my fantasy.”

For his first residency, in 2021, at the Colosseum at Caesars Palace — Hammerstein’s first, too — they devised a preshow immersive “experience” for 150 audience members, bringing them up close with performers as they enacted scenes representing different elements of Usher’s career before leading them into the theater for the main show.

Soon after that residency ended, at the top of 2022, Usher decided to totally reimagine it with Hammerstein, who stayed on as creative director. They did away with the preshow experience and gave the main show the same immersive feel — starting with its very beginning, which is, well, hard to tell is the actual beginning. “The challenge was to show it’s not by chance we had success in Las Vegas,” Usher says of My Way. “We deliberately made decisions that would elevate your thinking on the evolution of who I am as a creative.”

That’s the ideal residency outcome, and Usher’s manager, Ron Laffitte, knew that well: After his clients the Backstreet Boys staged a residency at the Colosseum from 2017 to 2019, they were able to launch an ongoing global tour and a new chapter of their career. “I just don’t think there’s another platform in the world [like Las Vegas] where you can go and illustrate an incredible career and showcase the fact that he’s as relevant today as ever,” Laffitte says of Usher. “And I think this residency has done that.” Usher’s first residency sold out 18 of 20 shows, grossing $18.8 million, according to Billboard Boxscore, and My Way sold out its opening run of eight shows. As for catalog streams, says Laffitte, “All boats rise with the tide, and the tide has risen dramatically.”

Residencies are often called “the Broadway of pop music” for good reason: They let creative directors help artists tell stories about themselves, however abstractly, in a way that showcases both their hits and the fact that they are more than the sum of those hits. PLAY (which opened in late 2021) has an Alice in Wonderland-tinged narrative and oversize Pee-wee’s Playhouse-esque sets, perfectly embodying Perry’s knowing wit and cartoonish creativity. Legend’s Love in Las Vegas spotlights his skills as a pianist-balladeer but takes him through nouveau Soul Train, church and urban street scenes to flesh out how his multifaceted talent developed. An Evening With Silk Sonic, with its thoughtfully constructed club staging, places Bruno Mars and Anderson .Paak’s musicianship front and center.

Those are best-case scenarios. A creative director who’s perfect for one artist might not gel with another — and even a star can be stymied by partnerships that go sideways. No one interviewed for this story wanted to discuss the troubled history of Adele’s much-awaited Colosseum residency, set to begin in November. (A representative for Adele declined to comment on creative direction for the residency, as did Caesars Entertainment and Live Nation.)

Originally intended to open in January 2022 — which is, oddly, why Usher moved to the bigger Dolby Live for My Way — Adele postponed her show at the last minute, apparently due to core creative issues. She has since hired a new production team, including creative director Kim Gavin and stage design firm Stufish; her original main collaborator, set designer Es Devlin (who also declined to comment), is no longer involved. Adele recently told Elle that in the original production, there ultimately “was just no soul,” that “the stage setup wasn’t right,” and it “lacked intimacy.” Which are exactly the kinds of problems the right creative director can help solve.

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Just as artists rely on creative directors, those directors need their own support to succeed. “Very rarely in your life do you meet someone who can just take your mediocre ideas and make them better with an immediate shorthand,” says Hammerstein with a self-deprecating laugh. “And I have so many bad ideas. But Aakomon is a great filter for them.”

“He’s exaggerating when he says they’re bad,” Jones, 43, says with a smile. With his preternatural calm and warm demeanor, he’s the yin to Hammerstein’s impish, let’s-put-on-a-show yang. “But he’s not exaggerating when he says he has a lot. One of the most impressive things about Simon is he’s literally a conduit for creativity.”

Jones, who spent years dancing and choreographing for Usher before becoming his creative director, is someone who “understands my language, understands the history I’m attempting to tell and the importance of our culture out of Atlanta,” the artist says. He also understands big-picture stage thinking: Jones previously put together showcases for artists seeking recording contracts, and more recently, he has worked extensively choreographing for film and TV. Considering that background, Jones says, Hammerstein was “a perfect blend of those two worlds. He’s a phenomenal storyteller and character writer. And given the club-owner aspect of what he does, he knows people, he knows experience, he knows personalities.”

It was those qualities that drew Usher to Hammerstein long before the residency. He wanted the man who had created the vibe at The Box, but also someone who understood the way he had felt at Sleep No More, a long-running immersive theater production in New York (which Hammerstein did not work on) loosely based on Macbeth. Masked attendees follow a sprawling ensemble through a multifloor space filled with mysterious scenes. They watch the performance as voyeurs who come to feel part of the scenes and piece together the story based on the path they take through the space.

Usher knew that, with Hammerstein and Jones’ combined insights, he could achieve something similar in My Way. “To me, this is a chance to find a narrative that makes you look at live performance in a little bit of a different way,” he says. “I understand theatrical thinking and how things come to life onstage. My songs have always told a story. So how do I manage to encapsulate all the things I am in one night?”

For Hammerstein, like many creative directors, figuring out how that works in Las Vegas is the first step. “A tour is hardcore fans, people who have gone out of their way to see you — they’re paying for parking, merch; it’s an expensive night out,” says Halpin. However, a Vegas audience is just as likely to attract folks who make the show just one element of a night out. By the end of the event, everyone should be rushing to stream that artist’s catalog.

That means playing the hits — and even among those, the most streamed — is imperative. “We definitely looked through the catalog at what was the highest-rated, what got the most plays, and made sure those made the list,” says Tabitha Dumo of Nappytabs’ approach for Lopez’s residency. The setlist then draws an outline for the story the performance will tell, which the creative director can then execute with the tone and aesthetic the artist desires. “Smart creative directors aren’t necessarily there to impose their own vision — they’re there to help cultivate and refine and reimagine,” says Raj Kapoor, who creative-directed the Backstreet Boys’ residency and is now working with Lambert. Internalizing that idea has been central to Hammerstein’s success with Usher. “Simon has his own sense of what he wants to accomplish,” Laffitte says, “but I’ve always felt he was listening to Usher. He has honored what Usher wanted to create.”

Concert promoters have been known to suggest creative directors to artists who ask, and Live Nation keeps a shortlist of names, but the company will rarely offer feedback on their vision. If they do, it usually amounts to encouraging them and the artist to go for everything a Vegas stage can offer — say, the ability to add a curved extension called a passerelle to the Dolby Live that can transform the venue midshow into a funky, Atlanta-style roller rink, as Usher does. “We just sort of say, ‘Look, it’s Vegas. Your palette can be bigger, bolder, more exciting than any other show you’ve done,’ ” says Live Nation’s Moore-Saunders. “Have fun with it.”

Going big still means staying within budget, though. “Ultimately, you still have to make money,” says Napoleon Dumo, who is still proud that he and Tabitha kept Lopez’s show within budget. “That’s the biggest thing we’ve learned as creative directors. There’s a zillion creative people in the world who could come in and say, ‘I would do this!’ And before you know it, you’re spending a million dollars a week, and you just don’t have that.” Judging when, what and to whom to say “no” may be the hardest part of the job. “You could have this amazing vision — poetic, stagecrafty stuff — and if it’s not serving the arc of the show, it’s just you being self-indulgent and showing off,” Hammerstein says.

On opening night, synthesizer blasts introduce “Yeah!” — and signal both the end of the show and the moment Hammerstein and his team agonized over. With the audience completely on its feet, the stage transforms into a giant party. The gravity-defying pole dancers, the skaters, the dancers and Usher himself all unite at the front of the passerelle, which brings them further into the audience. As the outro plays, a snowstorm of Ush Bucks float down from the ceiling, and a woman next to me maniacally screams: “That was better than Caesars!”

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A month after My Way opens, Usher is back in Atlanta, getting his two older sons ready to return to school. When the show resumes — for August, September and October dates, and then for a just-announced additional slate of 25 shows starting in March 2023 — he will go back to Vegas and treat it as home. “My family is there with me,” he says. “I enjoy being able to be active and not lose my normal everyday steps.”

Speaking to Usher the dad — who, at 7 o’clock on the dot, is putting his babies to bed (not in his drop top cruising the streets, as he sings in “Nice & Slow”) — feels like an appropriate coda for My Way. Hammerstein had described the show to me as “part musical, part concert, part opera, part Brechtian theater” and also as “a night of heartbreak and catharsis but also celebration and joy and fun.” But one could more simply say that My Way traces Usher’s existential journey, just as he has documented it for decades through his songs. Like a Sleep No More voyeur, he moves through scenes that capture the Ushers he has been before: the dancefloor superstar, the Atlanta strip-club denizen, the romantic, the man who gives in to temptation but eventually learns to overcome it.

“Simon has really helped architect that journey,” says Laffitte. But the end product also works because of the team Hammerstein has had in place since the first residency, all of whom understand the show’s theatrical underpinnings. Without that, plenty of first-time creative directors fail. “I see a ton of really talented new creative directors who could have a great future. The artist sees their Instagram, they want the new-new, they vibe, they come in all gung-ho,” says Halpin. “But you don’t know what you don’t know, and there’s no support system a lot of the time.”

Hammerstein, on the other hand, had Jones, whom he calls “a real man of the theater,” by his side, as well as an extended creative team including everyone from Paul Tate dePoo, a Broadway veteran, to Hammerstein’s longtime business partner, Richard Kimmel, who has worked as an associate of New York’s storied downtown theater troupe The Wooster Group and acts as his co-creative director for My Way. Their chemistry with Usher (who happens to have also done Broadway: Chicago in 2006) comes from a common understanding that “it’s about what works best for the audience,” says Usher. “It’s not easy to find the English of this experience, the language that everyone understands. But I like to be challenged — I like that they’ve made me work to prove my point.”

Residency creative direction is still a job for which there’s no clear preparation — or career path. Hammerstein and Kimmel’s company, Outside the Box Amusements, has other projects on the immediate horizon — a new nightclub in London “reimagining what cabaret and drag and dinner theater mean today” and some “opportunities in Vegas that aren’t concerts but are taking over large-scale spaces, programming and curating them.” If the right artist comes along, though, they’re eager to do another residency, and they now have a big promoter on their side. “I would love to have Simon and his team do another residency,” says Live Nation’s Moore-Saunders. “I can imagine artists who would be so cool with him.”

For now, Hammerstein is back in London — but not entirely done with the world of My Way. Change is the norm for a residency like this, long after opening night. “When you see it with a live audience for the first time, you really know what works and what doesn’t,” says Kapoor. “So the shows have to be a bit fluid — you see what you can do to continually improve it.”

For Usher, that has meant rethinking assorted elements, including that much discussed ending. “I’ve got this weird kind of divide between the artist I became and the artist I was, the artist I am,” he says. “Finding that balance to make sure everyone’s pleased, I listen to critiques.” He has heard feedback from Antonio “L.A.” Reid, Jimmy Iovine, Terry Lewis, his mom, fans at meet-and-greets. The immersive feel of the “Yeah!” party, Usher realized, backfired in one way: The audience didn’t seem to totally grasp that the show was actually over.

Usher’s team also noticed that, during the section of the show in which Usher performs from the audience on the DJ booth — cycling through years of his hits like hitting the Seek button on a live Usher radio station — the crowd responded overwhelmingly to his EDM-infused anthem “Without You.” “It has an emotional gravity to it,” Hammerstein admits. So they made it the new ending, after “Yeah!,” a final moment of connection for Usher — and for the sea of phones in the audience to capture.

Phone screens are, as Usher puts it, the “fourth wall” for his show. “We’re creating a new idea, bringing all these worlds together, and the final piece of it is literally the device in your hand,” he says. He hopes My Way is captivating enough to make attendees put their phones down. But he also knows he’s not the only show in town and that viral moments are powerful. During his recent NPR Tiny Desk concert (which took place, in a happy accident, right before My Way opened), he knowingly made a move while singing “Confessions Pt. II” that became the “Watch This” meme — and because, as Laffitte puts it, “momentum creates momentum,” that no doubt directed plenty of new ticket buyers to My Way. So when clips of the world he has created with Hammerstein and Jones show up on Instagram Stories, he’ll embrace it. “If you do manage to capture some of it, what it creates is FOMO,” he says with a knowing grin. “The rest of the world sees it, and they feel like they’re immersed, too.”

This story originally appeared in the Aug. 27, 2022, issue of Billboard.