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Two days before the 2019 Grammys, much to the chagrin of her team, Janelle Monáe went skydiving. Her album Dirty Computer was nominated for Album of the Year, she was scheduled to perform, and still she and some adventurous friends drove two hours outside Los Angeles on a clear and sunny afternoon. They watched a training video about the inherent risks of throwing yourself from a plane with only a parachute to bring you safely back to earth. As Monáe waited at 14,000 feet, preparing to dive into the great wide blue below her, she was ready. If she died, she thought, at least she would die doing what she wanted. She stared down and marveled at how small the world seemed — tiny houses, tiny cars, tiny people — and in that moment, she felt fearless.

There was something cathartic about that jump, the exhilaration of flying through the air and the simple satisfaction of realizing she had the courage to make that leap. It was the beginning of what would become a year of introspection and evolution for Monáe. “I wanted to skydive into different parts of my life,” she said when we met for dinner in L.A. We were ensconced in a booth in a darkened corner of a private club in West Hollywood where celebrities and other assorted fancy people have to put stickers over their camera lenses before they gather to eat and drink and see and be seen. It’s a silly gesture, because what can be applied can just as easily be unpeeled, but, like airport security, I suppose, it allows members to feel like their privacy is safe.

Monáe was dressed sharply in a matching three-piece suit — black-and-gray pinstripes, a cream-colored silk shirt with wide cuffs, a wide-brimmed black hat, two different earrings, and high-heeled cream booties. Her hair was long, wrapped in a thick braid cascading down her back. As we walked to our table, in a city where a great many people are powerful and gorgeous, so much so that they become unremarkable, she turned heads. She is known for always sporting a different look — a red tuxedo, a thickly brocaded black-and-white dress with a wide skirt, braided buns on each side of her head, a pompadour, her hair slicked close to her scalp. She has absolutely flawless skin, and I often want to ask her about her skin-care regimen, but I never do because I only use water and shower soap and Jergens lotion. There’s no use pretending I would ever expend the energy to do anything more rigorous than that.

We began our conversation talking about the stories Monáe wants to tell — stories that are bold, honest, ones that can shape the culture and have a specific point of view. In many ways, at least to me, Monáe was describing her own body of work. She is ever evolving, experimenting with her aesthetic and her sound, refusing to limit herself professionally or personally. She is daringly herself in an industry that often demands conformity and punishes originality. She actually looks like she is having fun. And still there is an interesting tension in her work: She creates music that allows people to feel seen while maintaining firm boundaries around how much of her truest self we will ever really see.

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When I asked her what an Afrofuture looks like, Monáe said, “Right now, it looks like an orgasm and the big bang happening while skydiving as Grace Jones smiles.”

Janelle Monáe Robinson was born on December 1, 1985, in Kansas City, Kansas, where she nurtured a desire to perform, as did her large, matriarchal family. She participated in talent shows and high-school musicals to hone the ambition that, she says, was in her DNA. Monáe’s mom and grandmother instilled a strong work ethic in her, perhaps too strong. When she looked back at her 2019 calendar, she realized she had gone from project to project to project and was emotionally spent. She began to recount everything she did last year; even as a workaholic myself, I found it exhausting. After the Grammys, she performed at Coachella, then she filmed Antebellum and then another movie, then she was in preproduction for a television show, and somewhere in there she went on tour, and then the show was in actual production.

New artists are often forced to say yes until they have the power to say no, to compromise their integrity until they have the power not to. Monáe, however, is different. “At the beginning of my career, I always said no.” she said. “ ‘Nope, nope, nope.’ That was my secret weapon. Once I started to eliminate the things that didn’t feel in line with where I was trying to go, and that could potentially pigeonhole me from having that freedom as an artist, it was very helpful.” That selective approach to curating her early career led to the bounty Monáe is currently experiencing. She so distinctly defined who she was that the industry took notice and, in its way, bent to her creative will.

As she began to assert herself, Monáe was drawn to the idea of the android — someone who is part human, part robot — in order, she now reflected, to protect herself. The android persona gave her a mask beneath which she could hide, something more perfect to which she could aspire. With her debut, a concept album titled Metropolis: Suite 1 (The Chase), she took on the persona of an android, Cindi Mayweather, and would continue to play with that persona and a musical blend of neo-soul and synthesized beats with a hard-rock edge for two more albums, The ArchAndroid and The Electric Lady.

She had long been interested in science fiction and Afrofuturism, which, for Monáe, represents “the full spectrum of our blackness; where we come from, our present, and our future.” She takes an expansive, imaginative view of this spectrum. When I asked her what an Afrofuture looks like, Monáe said, “Right now, it’s Lil Uzi Vert being happy with orange locs, Erykah Badu doulaing, Octavia Butler’s voice, Stacey Abrams being president and punching Trump out the Oval seat, black people getting passports and hanging out in Africa, black queer lovers holding hands while the pastor smiles, George Clinton’s sunglasses in 1974, Prince’s eyeliner in Under the Cherry Moon, black bodies walking away alive after a police stop, Tierra Whack and Ari Lennox joking on Twitter, black kings in nail polish, Lupita’s performance in Us. It looks like an orgasm and the big bang happening while skydiving as Grace Jones smiles.”’

This eclectic vision echoes across all of Monáe’s music. “Dirty Computer was really a reflection of where I was at that time. I was discovering more and more about my sexuality. I was walking into being more sex positive, also understanding different ways to love and to be loved,” she said. The album was accompanied by a 46-minute “emotion picture,” in which Monáe plays Jane 57821 in a society where people who don’t conform are “dirty computers” and must have their memories erased to clean them into submission.

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It is a vision of a dystopian society, responding to our current dystopian moment. Monáe was motivated by the fear she felt after the 2016 presidential election, fear for her safety as a black woman in a world where white supremacists were newly emboldened, fear for the political trajectory of the country. That anxiety fueled the music. She decided to make the album unapologetically black and radical. “It started with who don’t I mind pissing off,” Monáe said. “I don’t mind pissing off conservatives. I don’t mind pissing off white men. I don’t give a fuck. This is about celebrating. I wanted to celebrate queer black people living outside of what it meant to be American.”

I feel my feminine energy, my masculine energy, and energy I can’t even explain. — Janelle Monáe

Monáe has always been brash and relentless and political in her work and in how she moves through the world. In 2015, she released the song “Hell You Talmbout,” on the scourge of police brutality. The lyrics demand that we say the names of black men and women who have been murdered by police. While introducing Kesha’s performance at the 2018 Grammys, she said, “We say time’s up for pay inequality, time’s up for discrimination, time’s up for harassment of any kind, and time’s up for the abuse of power.” Recently, she tweeted #IAmNonBinary, and, as you might expect, people wondered what she meant. When I asked, she said, “I tweeted the #IAmNonbinary hashtag in support of Nonbinary Day and to bring more awareness to the community. I retweeted the Steven Universe meme ‘Are you a boy or a girl? I’m an experience’ because it resonated with me, especially as someone who has pushed boundaries of gender since the beginning of my career. I feel my feminine energy, my masculine energy, and energy I can’t even explain.”

Over the course of our conversation, I realized Monáe is one of those artists who have an interesting response to every question. She is deliberate in what she says, purposefully provocative in ways that serve to reinforce her carefully crafted public image. She is well read and voraciously curious. There is a private person behind that image, but it’s difficult to truly know who that person is, who and what she loves, what brings her true joy, what she most yearns for. This is not to say we didn’t have an intimate conversation, because I think we did, but it was an intimate conversation within very specific boundaries. I very much wanted to ask her about her pansexuality and some of the famous women she has been associated with, so I asked Monáe if she was in a relationship. She smiled demurely and said, “I don’t talk about the folks I’m dating,” and we left it at that.

She likened the public interest in her personal life to fanfiction; people take what they think they know of her and create stories that are nothing more than figments of the public imagination. And I suppose she’s right. That is what we do with celebrities. We finish the incomplete stories about their lives that they offer us in ways that fulfill our own needs and wants. Monáe wasn’t closed off, though. She was merely circumspect in entirely reasonable ways. Among other things, she shared that motherhood is one of the dives into the unknown for which she is ready. Like many people, she is trying to find the right time professionally to take a step back to have a child. She wants to make sure she is healthy enough as she recovers from mercury poisoning, which she got after becoming a pescatarian. “I started feeling my mortality,” she said.

Though she has been spending more time in Los Angeles, Monáe is based in Atlanta, where she collaborates with the Wondaland Arts Society, an arts collective determined to spread its reach to every aspect of the entertainment industry. Wondaland is, in Monáe’s words, a “school for mutants and droids” and comprises an intimate group of young, black creatives who want to “piss off the Old Guard of gatekeepers who don’t understand the value of black-renaissance artists.” Monáe is a radical voice looking for other radical voices, and she has built a career on that kind of forward thinking. These days, she is trending toward being as accomplished an actor as she is a musician.

Monáe made her film debut with supporting roles in two movies — the Oscar-winning Moonlight and Hidden Figures. In April 2020, she will star in Antebellum, a “mind-bending social thriller” from the producers of Get Out and Us. She plays Veronica, a writer with a strong sense of social justice. Details on the film are intentionally vague, but Veronica finds herself in a horrifying reality (the trailer suggests she’s trapped in an alternate reality where she is enslaved) and must solve the mystery of how she got there before it’s too late. It is reminiscent of Octavia Butler’s work, shaping a black future that is inextricable from our past.

Veronica was Monáe’s most difficult role yet, with a rigorous filming schedule and the pressure of leading a major motion picture for the first time. These pressures were magnified by the way she works as an actor — the role tends to follow her home during filming. “I want that spirit to always stay on-camera so I don’t break. I don’t talk on the phone a lot … I don’t want that to take me out of my space.” Monáe allows her characters to subsume her. And that approach certainly takes its toll when she is choosing to “dig in and stay there” in a role that deals with trauma. Despite the rigors of her craft, acting is still therapeutic. “I use my pain,” she said. “I use it.”

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The club emptied out as the evening waned, and Monáe suggested that we repair to Wondaland West, the Hollywood Hills home she rents when she is in town. As we were leaving, a seemingly drunk man with strategic scruff and a deliberately casual manner waylaid her. He introduced himself and told Monáe he wanted to talk to her as if he had something of the utmost importance to say. He did not. I stepped aside to give them privacy but did not put too much distance between us because he was clearly hitting on her and she gave no impression that she was at all interested. A few minutes later, as we walked to the curb to wait for our cars, she thanked me for not leaving her alone. Sometimes celebrities really are just like us, tolerating the attention of obnoxious men with terrible beards.

Wondaland West is one of those homes with a pristine and spectacular view of L.A. Inside the house, there was a large orange trunk I recognized immediately as Beyoncé’s new Adidas x Ivy Park collection, which would drop a few days later. Janelle Monáe has got it like that, I thought to myself as I stared at the trunk and its contents covetously. I was, I felt, as close to Beyoncé as I had ever been or would ever be. It was a holy moment.

Several members of the Wondaland team gathered to greet me in a flurry of names and kind faces, and I was immediately struck by the genuine camaraderie and affection the group shared. Earlier in the evening, Monáe had said the Wondaland team is a family, but that’s something lots of people say, so I didn’t know it was true until I saw them together. They bantered, talked trash, and opined on any number of things, including the 2020 Oscar nominees, the joys of Peloton, and something about “daily rankings.”

On a nearby kitchen counter, a fragrant dish was cooking in a Crock-Pot. There was an open Popeyes box. A man sat on the couch with his feet on a pedal exerciser, and another man was slowly cycling to nowhere on a Peloton bike. Four of us immediately sat down to play Rummikub. I am extremely competitive, so once I refamiliarized myself with the game’s rules, I was determined to dominate. Monáe is competitive too, as was everyone else. It didn’t occur to me until much later that perhaps I should not have been playing to win. The game proceeded apace. I concentrated, studying the game board and my tiles with an undue amount of intensity. My goal, mostly, was to not embarrass myself. Imagine my surprise when I won the first game. I felt stupidly flush with victory.

We immediately began shuffling tiles for a second game. Monáe remarked that the game helps her relax and focus. Sometimes, when she is creatively blocked, a good game of Rummikub will help her reach a much-needed breakthrough. The second game was more competitive. I ran the permutations of possible moves over and over in my head as I waited for my turn. I knew what I needed to do to win again. And just as I was ready to lay down my final tile, Monáe, who had been deliberating for quite some time, found her final move, laid down her tile, and won the game. “At least this game was closer,” I quipped, and everyone began to laugh.

It was interesting, though, to see how determined Monáe was to win, that her ambition extended even to board games. Earlier in the evening, I had asked her if she could ever achieve enough, and she admitted, “I feel like there’s never going to be enough.” Even early in her career, she hustled, cleaning houses, working in Office Depot, starting to form her tribe, some of whom were in that house playing Rummikub with us. She used the money from her day jobs for studio time. She was pressing her own CDs and selling them out of her car trunk. All the while, she was thinking about the kind of artist she wanted to become. She was thinking about what she was and was not willing to compromise. She was willing to sacrifice becoming a household name to create honest work. She was not going to sacrifice her freedom for fame, and as I looked around that table, it was clear she was surrounded by people who would hold her to that. I asked Monáe what she likes most about her work. “I like how my work reveals itself over time,” she said. “It’s like a letter you wrote yourself ten years ago, but when you open it in the future, things start to make sense.”

After the second game, it was well after midnight, time for me to go home. We assembled around the Beyoncé box, admiring the array of Ivy Park merchandise. Monáe donned a maroon parachute cape, went outside, and began running around the pool deck, the cape billowing behind her, a bright smile stretched across her face. For a moment, as she began to catch the wind in her cape, it looked like she might soar off that deck, still fearless.

*A version of this article appears in the February 3, 2020, issue of New York Magazine. Subscribe Now!