He has the longest-running Hot 100 hit of all time and could soon win Grammy gold, but Lil Nas X is determined to stay weird -- and refuses to be categorized.

Eventually, there will come a day when Lil Nas X runs out of new terrain, when he has finally ridden so far down the Old Town Road that he can ride no more. This is not that day.

It is early evening on a Monday, and Lil Nas X, 20, is backstage at the Prudential Center in Newark, N.J., getting ready for the MTV Video Music Awards. He has just walked the red carpet in a silver sequined suit, ruffled shirt and silver cowboy boots -- a little yee-haw mixed with the rock-star flash of Little Richard and Prince.

Later, Vogue will opine that the look -- from designer Christian Cowan, whose clothes can also be seen on the cover of Cardi B’s Invasion of Privacy -- “may just be the most dazzling interpretation of the boundary-pushing” men-in-lace trend. Lil Nas X’s own evaluation is more succinct: “It’s a little disco ball.” His voice is low and slow, with a bit of Southern syrup, and he’s tall (6 feet, 2 inches) but not imposing, his magnetism a mix of unshakable brio and vulnerability. After the disco ball crack, he flashes the slight smile that lets everyone around him know that they’re in on a joke -- and maybe a world, too -- of his own creation.

But right now he needs to ditch the disco ball and get into his stage gear: a Tron-meets-laser tag light-up ensemble requiring wires, battery packs, tape and a team of four people to make it all work. The process takes over 30 minutes, the majority of which Lil Nas X spends checking his phone as his troops -- a 20-member dance crew, and a chunk of the Columbia Records executive team -- rally around him.

Back in March, chairman/CEO Ron Perry signed Lil Nas X to his label after DM’ing him on Instagram. (Lil Nas X wasn’t getting back to Columbia’s A&R team, but he liked the look of Perry’s feed enough to respond. He also liked the look of Perry’s hair, which defies gravity in the rock-star tradition of Rod Stewart and Robert Smith.) What happened after that is modern pop-music history. Fueled by its remix featuring Billy Ray Cyrus, Lil Nas X’s laconic hip-hop-meets-country track “Old Town Road” shot to No. 1 on the Billboard Hot 100 and stayed there for 19 weeks, making it the chart’s longest leader in history. Columbia is enjoying a bump in current market share, up to 6.09% year-to-date from 5.67% in 2018. Without Lil Nas X’s 2.32 billion on-demand U.S. streams (according to Nielsen Music), the label would be flat against last year. (If RED and its labels are excluded from Columbia, its market share is up more than one percentage point to 4.38% from 3.32%, with Lil Nas X accounting for about 58% of the increase.)

No song has defined 2019 more than “Old Town Road,” but tonight’s VMAs performance is intended to shift attention to what’s next: Lil Nas X’s second single, “Panini” (improbably named not for a sandwich, but for an Adult Swim cartoon character). MTV would have preferred he include “Old Town Road,” but Lil Nas X says he “wanted to move on,” making this a pivotal moment. He rode to fame as a pop-music insurrectionist, rallying the support of a generation operating, as he did at the start, outside the sightlines of industry gatekeepers. Now Lil Nas X is inside the gate and facing a much bigger stage. When this year’s Grammy nominations are announced in November, he will be a strong contender not only for best new artist but for record of the year, maybe even song of the year. To win the hearts and minds of Grammy voters, he’ll have to show he’s not some internet-birthed curiosity, but a multidimensional artist.

At the VMAs, he’ll execute stage one of that­ transformation: Urban Cowboy to Pop Star With Dance Moves. This is no small feat, considering that prior to April 28 -- when he and Cyrus joined Diplo at Stagecoach for the first-ever live performance of “Old Town Road” -- Lil Nas X had never really been onstage in front of an audience. “It’s not like he got the chance to go play clubs and theaters and put in his 10,000 hours,” says Adam Leber, who co-­manages Lil Nas X at Maverick with Gee Roberson. Again, Lil Nas X is more succinct: “I didn’t know what to go out there and do.”

Performance consultant KJ Rose, who toured as a backup singer with Britney Spears, *NSYNC and Diddy, stepped in to assist. “We had him in rehearsals almost immediately,” says Leber. “He worked his ass off.” Rose, who’s on hand again for the VMAs, says she simply wanted to unlock Lil Nas X’s potential -- to free him to “occupy his space.”

“She helped me get some confidence to go out there and do a little two-step,” says Lil Nas X.

The VMAs, though, require more than a two-step, and Lil Nas X has prepared for the past week and a half, rehearsing with two chor­eog­raphers. Yesterday, at a full-tech run-through, the results looked promising, if not perfect. “I didn’t know he could dance like that,” Phylicia Fant, Columbia’s co-­president of urban music, said at the time. “We went from the scoot-scoot to...” -- she gestured to the stage, where Lil Nas X was getting tape applied to his shoes to help him with a few seconds of moonwalking.

Tonight’s performance serves as a preview for the sci-­fi-­themed “Panini” video -- for which Lil Nas X wrote the treatment himself -- and it’s preceded by a fake newscast celebrating the 3,162nd remix of “Old Town Road” in the year 2079. It’s a smart wink, the kind of detail he sweats. “Old Town Road” may have seemingly come out of nowhere, riding a beat Lil Nas X purchased online for $30, but he spent a month fine-tuning the verses and melodies, and he has crafted a new version of “Panini” for the VMAs with a live drum breakdown, upping the rock quotient of a rap song that interpolates the melody of Nirvana’s “In Bloom.” Onstage, says Lil Nas X, he’s hoping to achieve “a boy band meets current dance kind of thing.”

It’s almost time to head downstairs. Stylist Hodo Musa gathers everyone into a circle, where, hands joined and heads bowed, Rose leads them in a prayer. “Lord,” she asks, “let this man be a vessel for those who are not heard and those who are not seen. Let him step into the light of this moment. And let him have fun.” A collective whoop goes up, hushed for a moment as Lil Nas X holds up his hand. “I want to pray,” he says as all eyes turn to him, “for the arms and legs and bodies of these dancers.” And then an amen, and that smile again, slight and sly.

Ask Lil Nas X if he feels any pressure following up the record-­breaking “Old Town Road,” and you’ll get a simple answer: No. “I’m not worried about anything,” he says over lunch a few days after the VMAs. Sure, “Old Town Road” has created an identity for him, but he’ll create others. “As an artist building myself up, I’m going to have to continue to make other moments,” he says. “But it’s not something that I’m upset about or anything. I mean, maybe when I’m out in public and someone asks for a picture and they’re like, ‘Where is your hat?’ ”

Anxiety is not his thing. Did he feel nervous at Stagecoach? “I really don’t think I did.” (Leber, on the other hand, “was panicked. He has never done this and there’s 10,000 people. This guy got onstage and it was as if he had done this 4,000 times -- couldn’t be more natural -- and got offstage like it was nothing.”) How about when he joined Miley Cyrus at Glastonbury before a crowd of over 100,000? “I felt the energy.” Certainly, coming out as gay in June (“some of y’all already know, some of y’all don’t care” he wrote on Twitter, pointing to the lyrics of his song “C7osure”) must have stirred some nerves? “Just like, rip the Band-Aid off,” says Lil Nas X, though he allows that it was “nerve-wracking” to come out to his father earlier that month. “It’s something I never probably would have did if I was still living with my parents. I have that independence to do it, you know?”

In person, Lil Nas X operates at a slight remove, and it’s hard to say if he’s being observant or detached -- his mask of cool never drops. This is true even when he at last admits that earlier this year, when “Old Town Road” was picking up speed but hadn’t yet achieved escape velocity, he was sleepless, and caught in a tangle of worry and weed smoke.

He had only been making music since the summer of 2018, while he was living at his sister’s house after his freshman year studying computer science at the University of West Georgia (he grew up in Austell, outside Atlanta), hoping to create the next great app. “The blueprint of something huge more than the actual coding,” he explains. College was pretty easy, with the exception of his first F in math. “With math I spent most of the year half-­assing it just so I could get by, not so I could exceed. I would smoke all the time, and [then] the end of the year is coming and I have to make up this grade, and the teacher is like, ‘Oh, no, we don’t do extra credit.’ ” He was supposed to make up the course online. Instead, bored, “I made my first song.”

Rapping over some beats he found on YouTube, he started using the name Lil Nas X. “I was just trying to fit into a certain spectrum,” he says. “Just like, basic rap.” These tracks, collected on the Nasarati mixtape, are full of expletive-­laced boasts about smackdowns, diamonds and luxury cars. On two, he talks about having choppas in the truck, though when I ask if he has ever owned a gun or a truck, he dissolves into silent laughter. “I still ride in Lyfts,” he says. “I haven’t got a license yet.”

Still, those two songs showed his instinct for harnessing the power of the internet for his own purposes: They’re titled “Kim Jong” and “Donald Trump.” He had amassed a six-digit Twitter following with this kind of thinking -- pushing out memes and threads that rode whatever was viral at the moment (or about to be so), trying to be “on the next wave before it’s even there.” He wanted to “build and build my personality on the internet and a bigger base -- reaching wider audiences of all kinds. Keep going until you actually find something you can profit from, which I did, luckily.”

It happened once he stopped making “basic rap” and began making music that matched his online personality -- specifically, a song rooted in an idea that wasn’t at all basic, that mixed the funny meme culture he loved with hip-hop bounce and country gravel, that was short, to the point. He released “Old Town Road” on SoundCloud and iTunes last December, then spent all his waking hours pushing the track online, creating memes or laying search bait on Reddit to jump-start interest. He’d smoke weed anytime he came across a little, just to ease his mind.

“Because I’m always thinking: What if I’m not promoting the song hard enough? What if this never goes for me?” he recalls. “I was sick because of smoking, not sleeping because I’m always promoting my music. I was stressing so much more during that period because it was my first song to move at this height, this speed. One wrong step and it can all slip up.”

When he discovered that the beat he had bought contained a Nine Inch Nails sample, it felt like the one wrong step he had been dreading. “The song was nowhere near the real takeoff it was going to have,” he says. “I was like, ‘Oh, my God -- they find out about this, they’re going to get this taken down and I’m going to have to start all over.’ It was like a race against time.”

When Ron Perry first reached out to Lil Nas X on Instagram, he told him he’d make “Old Town Road” the biggest song in the world. What impressed Lil Nas X more was that when they first spoke on the phone, Perry understood not just “Old Town Road” but the Nasarati mixtape, too. “Within those songs that to most people all sound the same, he was able to differentiate the things that made each their own,” says Lil Nas X. More importantly, Perry didn’t want “the same song over and over. With any label I just felt like they would have said, ‘Hey, why don’t you make an entire country trap EP?’ He knew from the start that I had potential to be a great, versatile artist, which I already saw myself as.”

Columbia gave him the creative control he wanted and helped sort out the publishing on “Old Town Road.” (Nine Inch Nails’ Trent Reznor and Atticus Ross have 50% of the original track’s publishing.) The label also helped realize an idea Lil Nas X had first floated on Twitter in December, the day after he released the song: a Billy Ray Cyrus remix.

Initially, Columbia considered featuring a more current country star, someone who would guarantee country radio play. But Jennifer Mallory, Columbia’s GM, says it made more sense to amplify the narrative Lil Nas X had already created online -- one that caught fire in March when Billboard took “Old Town Road” off of the Hot Country Songs chart, where it had cracked the top 20. “It created a sense of curiosity around this track, so people wanted to go hear it,” says Mallory. “And it created a sense of him as an underdog, so people were rooting for him.”

Silvio Pietroluongo, Billboard’s senior vp charts and data development, emphasizes that it was “100% a purely internal decision.” “Old Town Road” was initially tracked on the country charts because Lil Nas X had listed it as a country song when he first uploaded it to iTunes and SoundCloud. As it gained momentum, Billboard examined it and the way it was promoted and marketed more closely, and decided it lacked “enough elements of today’s country music.”

“There’s definitely a problem where you can say this song is hip-hop, but you can’t say it’s country,” says Lil Nas X today. He points to Bebe Rexha and Florida Georgia Line’s “Meant to Be,” which spent 50 weeks at the top of Hot Country Songs, and which, like “Old Town Road,” has trap drums. “It’s kind of like saying that one of these genres has more respect. Take from that what you will.”

On April 9, Lil Nas X’s birthday, he got the news that “Old Town Road” had hit No. 1 on the Hot 100. “How did I celebrate?” Lil Nas X asks today. “I’d just became famous and rich, you know? That’s a celebration in itself. I didn’t really do anything else.” There wasn’t much time for anything else, anyway -- he was already in Los Angeles working on what would become his 7 EP. “When a meteoric track is going that quickly, it’s critical to get other music out so you can have a foundation,” says Mallory. “So it doesn’t become a one-hit thing.”

Lil Nas X’s first real studio session was with Daytrip, the production duo of Denzel Baptiste and David Biral, who worked on “Mo Bamba” with Sheck Wes and “Legends” with Juice WRLD. “We had a bunch of things prepared, more country-inspired, just in case that was really what he wanted to do,” says Baptiste. “But he didn’t. He put some of those aside and was like, ‘Play me your weirdest stuff.’ ” Lil Nas X asked to hear the “Panini” beat perhaps 30 times before he began rearranging it with Baptiste and Biral, taking out the first chorus to start with the verse, adding a prechorus, taking out the bridge. “Even though he didn’t know all the terminology, he knew exactly what he wanted,” says Biral. “He came in like a veteran.”

“There was a very real strategy here in terms of making sure that we had more music in the marketplace to showcase Nas as the artist we knew he was before everyone moved on,” says Leber. Seven or eight years ago -- when Gotye hit with “Somebody That I Used to Know” and Carly Rae Jepsen with “Call Me Maybe” -- “you worked your single into the ground,” he explains. “You didn’t want to cannibalize; you let it finish and you moved on.” Streaming has changed all that: It’s hard to call Lil Nas X a one-hit wonder when two of the other tracks on 7 have already charted on the Hot 100 (“Panini” peaked at No. 16 and “Rodeo” at No. 22).

But the multifaceted artist Lil Nas X has intended to be from the start -- the one who turned down the country trap beats, chasing something weirder -- is still emerging from the long shadow of “Old Town Road.” “It’s a really hard thing to pull an artist through a song this big,” says Mallory. “Sometimes the song gets bigger than the artist. In this case, he is pulling himself through it.” Columbia hopes the “Panini” video, followed by a remix with DaBaby, will drive the song back up the Hot 100. An Ellen DeGeneres Show performance and interview -- on Sept. 23, when Oprah Winfrey is also a guest -- will help introduce Lil Nas X to the moms of all those kids who drove his success on TikTok. For upcoming shows, “I think out of the gate we’ll probably do underplays,” says Leber. “But we have a different idea on how to do club shows. We want to create an environment where you come in, you can hang out for a while, there’s things to do and the artist takes the stage.”

As for Lil Nas X, he’s sorting it out as best he can from within the whirlwind. He bought an apartment in Los Angeles in June, but he’s not there much and hasn’t even had time to buy furniture (“I’m still sleeping on my air mattress”). It’s small for the two dogs he has now, so he thinks about a house, maybe in Atlanta. Buy land -- that’s advice Billy Ray Cyrus gave him. Cyrus also shared this wise counsel: When everything is moving too fast around you, just stand still. Sometimes Lil Nas X thinks he might need a vacation, but he worries about stepping away.

“I’m not as paranoid as I was before, but I’m still thinking if you miss too much you’re gone,” he says. “You step away from the public eye for too long, they don’t care no more. And whenever I do step away from the internet or the music too long, it’s like I have to slowly get back into myself to get back into the groove.” What groove? “Content. Making good content.”

This article originally appeared in the Sept. 21 issue of Billboard.