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In retrospect, the signs were there. The vintage arcade games on proud display in his 2008 episode of MTV Cribs; the 2011 album inspired by steampunk aesthetics; the impulsive commission of a $400,000 meme in the form of a chain that said “BIG ASS CHAIN” (which is currently on loan to the American Museum of Natural History for a forthcoming exhibit on hip-hop jewelry). But it isn’t until I step into the basement of T-Pain’s suburban Atlanta home — a neon-lit bunker with both a theater-size main gaming station and a separate arcade room with soundproof doors (“for screaming and sh-t”) and distinct areas for Atari, PlayStation, Tekken, Sega and SNES — that it fully sinks in. The man whose voice defined late-2000s party music is an unapologetic, card-carrying nerd.

“I’ve been trying to tell people for a decade!” the 39-year-old singer says with a booming laugh, pacing the game room in sweatpants and slippers. “Nobody wanted to listen.” Ten years ago, few would have known that the artist who seemed to write hits in his sleep was regularly hopping on Twitch to play Skyrim with like-minded gamers, or that he’d tricked out his Hit Factory studio in Miami with a full stage for nightly Guitar Hero sessions. (“Any time an artist would come by the studio, I don’t give a f–k what you’re talking about — grab this guitar and meet me in the booth,” he says, pantomiming Pantera-esque riffs.)

Back then, flying his geek flag in plain sight wasn’t compatible with being the voice behind the buoyant, world-conquering records that have soundtracked nearly two decades of bottle service nightclubs, pro sports broadcasts and White House correspondents’ dinners — at least not according to the powers that be. “I never got to show that side of myself because management deemed it uncool. So instead of playing video games, we’d go to the Dolphins game,” T-Pain remembers, his perennially jolly voice tinged with only a hint of regret. “But I thought that the sh-t I wanted to do was the coolest sh-t in the world.”

For listeners of a certain age, T-Pain’s music triggers Proustian memories of school dances, fake IDs and first sips of Boone’s Farm, the soundtrack to the nights that Facebook photo albums were made of. Back then, the Florida teen born Faheem Najm to a family of Bahamian Muslims had a stage name short for “Tallahassee Pain” and ambitions as a rapper that shifted when he heard the uncanny vocal effect applied to a remix of Jennifer Lopez’s “If You Had My Love.” In 2004, the 19-year-old inked a deal with Akon’s Konvict Muzik label, having caught the singer’s ear with a cover of his song “Locked Up” edited to be about having a busted car.

Tooling around on boosted equipment, he used vocal processing software to make himself sound like a choir of horny angels on his first hit, “I’m Sprung,” or an android on a bender on his next smash single, “I’m N Luv (Wit a Stripper),” both of which he wrote and produced as well as sang — and which both cracked the top 10 of the Billboard Hot 100 in 2005. Before long, his digitally uplifted melodies, sweet and slightly melancholy, had become the de facto sound of the charts. Between 2007 and 2008, T-Pain landed 13 top 10 Hot 100 hits, including three No. 1s (Flo Rida’s “Low,” Chris Brown’s “Kiss Kiss” and his own “Buy U a Drank”); for two weeks in 2007, he appeared on four top 10 singles at once. A dozen platinum and gold plaques hang throughout his basement, alongside an errant Grammy Award (best rap song for “Good Life” with Kanye West), a few plush toys designed in his likeness and a couple of White Claw empties.

But by the 2010s, the humanoid effect he’d pioneered had grown ubiquitous, oversaturating pop music to the point that its originator became a punchline. (“Y’all n—s singing too much, get back to rap, you T-Paining too much!” Jay-Z famously crowed on 2009’s “D.O.A. [Death of Autotune].”) Meanwhile, T-Pain’s own voice faded into the background. His fourth album, 2011’s Revolver, hardly moved the needle; its follow-up, 2017’s Oblivion, traded his signature melodies for middle-of-the-road trap he attributed to the demands of his then-label, RCA Records. He’s frank about the profound depression that colored the years in between; in the 2021 Netflix docuseries This Is Pop, he says it began on a flight to the 2013 BET Awards, when Usher called him over to accuse him of ruining music for “real singers.” (“We’ve spoken since and we’re good,” Usher told Billboard in 2021.)

The comment hit close to home. T-Pain had been struggling with alcoholism, mismanaged finances and an overall loss of creative confidence. “I didn’t want to do ‘Freeze,’ I didn’t want to do ‘Buy U a Drank,’ I didn’t want to do most of the songs that are my biggest hits. Because, you know, I’m an artiste,” he confesses in the basement with a chuckle and a deep sigh. “Back then, when I got done with a song, I was always thinking, ‘People are going to like this,’ and not, ‘I like this.’”

Over the past decade, Pain (as he’s known by his family and friends) has seemed hellbent on proving his artistic worth once and for all. In 2014, he arrived at his NPR Tiny Desk concert unaware of the brief, then sang gorgeous unplugged renditions of past hits on a video that now has 27 million views. He removed his furry monster suit to reveal himself to a stunned judges’ panel when he won Fox’s The Masked Singer in 2019, having anonymously out-sung Donny Osmond and Gladys Knight. And last year, he released a project he’d been piecing together since 2017, a covers album (On Top of the Covers) with source material ranging from Frank Sinatra to Black Sabbath, delivered with a full band and his soulful voice, au naturel. “I think it’s weird to even ask if I can sing anymore, or to even associate me with Auto-Tune in 2024,” he says matter-of-factly. “All the proof is there, and it has been there for a long time.”

T-Pain says he’d dreamed of recording a curveball like On Top of the Covers while his label and management team compelled him to chase the sound of artists half his age. (After 2017’s Oblivion, his last record for RCA, he signed to Cinematic Music Group, a subsidiary of Universal Music Group whose catalog was sold last year to Interscope Geffen A&M for an undisclosed amount, Billboard reported at the time.) After years of butting up against industry bureaucracy, he decided to go it alone, assembling a tiny team alongside his former project manager Nicolette Carothers to establish Nappy Boy Entertainment as an independent label in January 2020 (Carothers is currently the label’s head of operations). Besides T-Pain himself, it’s home to a small roster of rappers including Young Ca$h, with whom he released a joint eponymous album as The Bluez Brothaz, in March (and with whom he recently threw the Miss Biggest Booty Pageant in Atlanta, which is exactly what it sounds like). That umbrella has since expanded to reflect T-Pain’s truest passions, including Nappy Boy Automotive and Nappy Boy Gaming, both of which sell merchandise and host in-real-life and virtual events — from massive drift-racing competitions to a monthlong music competition on Twitch, which led to the signing of rapper NandoSTL.

Now, the hobbies he was once told to hide to maintain a veneer of cool are branches of his job, which means he’s basically always working. But for the first time in 20 years, he’s doing it his way — which generally means at home in sweatpants with a gaming console in hand. He gave up trying to come off as cool and has never felt cooler. Lit by the glow of five huge gaming monitors, he says with a shrug: “If you stop trying to impress everybody and make everybody think you’re perfect, what can they hate on?”

The day before we meet in early April, T-Pain posts a clip from a recent stream on Twitch, where he regularly broadcasts to a virtual crowd of gamers, fans, haters and random stragglers as he works on new music, plays video games or shoots the sh-t in occasional marathon sessions. (In recent weeks, they’ve ranged from five minutes long to 12 hours.) Previewing a new song, he noticed a string of comments from the same persistent heckler: “straight garbage,” “autotune to mask lack of skill” and so on. “My wife is one of my [moderators], and usually when people start talking sh-t, they get banned immediately,” T-Pain explains. “Then I started seeing the ban appeals: ‘I’m sorry, man. I was going through something that night, I was drinking heavy…’” He decided that rather than block out the hate, he’d figure out where it was coming from.

“I like all my sh-t, but I do know it’s ass to somebody,” T-Pain explained to the commenter on the stream in his usual jovial tone. “You think classically trained violinists are listening to ‘Buy U a Drank’? I don’t think so! But the thing we need to figure out is to stop trying to make everybody else have our opinion.” He went on to correct a few misconceptions (“People don’t realize, Auto-Tune or not, you still got to write a good song!”), analyze his own typecasting as “the Auto-Tune guy” and shrewdly break down club music’s escapist appeal. Before long, the random commenter apologized for his harsh words. “You ain’t got to apologize, bro,” Pain good-naturedly replied. “You just had an uninformed opinion.”

T-Pain has spent nearly two decades attempting to apply logic to comments like these. “They don’t want their narrative to change, especially if it fits in with everybody else’s: ‘Yeah, we all hate T-Pain. He’s bad at music,’” he says with a wry laugh. “If you’re a metal guy or a country guy, then of course all you’re going to know is the Auto-Tune, the narrative that has been pushed on you. But I’m here to talk through it with you, not to say, ‘F–k you, keep that opinion over there.’ Criticism is always good — but you’re not going to make me dislike my sh-t!” His level-headed breakdown is interrupted by a dramatic entrance from Stewie, the family’s Persian cat, who looks like a haughty, fluffy cloud and proceeds to cough up a series of noisy hairballs (and who is, yes, named for the Family Guy character).

When it comes to metal and country fans, T-Pain speaks from experience. Though the version of “War Pigs” that closes On Top of the Covers received Ozzy Osbourne’s stamp of approval (“Best cover of ‘War Pigs’ ever”), metalheads loudly disagreed. As for Pain’s soulful take on the country standard “Tennessee Whiskey” popularized by Chris Stapleton: “A country music page on Instagram posted my version, and there was only one comment: ‘Nope,’” he says, cracking up. It was harder to laugh at the reception of his previous attempts at country crossover. He recalls a red-carpet interview shortly after his “Good Life” Grammy win in 2008. “They asked me who I wanted to work with, and I said Carrie Underwood,” he says. “The country fans were like, ‘She don’t work with j—oos. She has too much class for somebody like you. Why would she ever…’ And I was giving her props!”

The topic will ring true for anyone who has listened to Beyoncé’s Cowboy Carter, but for T-Pain, the conversation isn’t new. “I actually lived in Nashville for a while, ghostwriting for country artists from 2014 to ’16. Everybody kept trying to figure out why Luke Bryan was saying ‘T-Pain’ in all his songs for a second,” he says with a laugh. Elsewhere among his clients: “Rhett Akins, Dallas Davidson… What’s the super racist one? Most of them?” he says with a cackle. “Toby Keith, I was writing stuff for him. Georgia Florida? Florida Georgia? Whichever way that goes.”

But after seeing his share of hateful feedback from gate-keeping country fans, he opted to keep his work private. “Beyoncé is strong enough to keep it going. It’s easier for her to stay in it than me,” he admits. “I’m not up at that level, so I can’t punch through that kind of stuff. So I kept doing it, but I just stopped taking credit.” Maybe those tides are finally turning: Running into Jelly Roll at the iHeartRadio Music Awards in April, the singer fawned over Pain’s “Tennessee Whiskey” cover, declaring, “Country music’s in love with you right now!” (And on April 26, the two released a cover of Keith’s “Should’ve Been a Cowboy” and performed it at Stagecoach together.)

T-Pain tends to refer to his work with a modesty that borders on self-deprecation, brushing off his biggest hits as inside jokes (he wrote “I’m N Luv [Wit a Stripper]” to make fun of a friend’s first strip club experience) or painful memories (the “Good Life” studio sessions dragged on for weeks). His fame still seems to puzzle him. “People will come up to me in the mall and I’m like, ‘My dude, we’re in Hot Topic right now,’” he says with a laugh. “I’m getting ear gauges just like you are, from the same case — actually, can you move? I can’t f–king see my earring.” Being a musician is nowhere near as cool as people make it out to be, he stresses: “Tons of people do way cooler sh-t than I do, and I know that because I look up to them.”

For the most part, the people T-Pain looks up to have nothing to do with the music industry. It was on a 2016 trip to Abu Dhabi, United Arab Emirates, that Pain discovered drifting, a style of precision driving seen in the Fast and the Furious franchise, which he describes as “being in control of an out-of-control car.” He was already an auto fanatic, at one point owning 46 vehicles (in part because his former managers knew that buying him a new one was the surest way to convince him to record a song). His former managers deterred his obsession with drifting, unsure how it could be profitable. Nevertheless, he began attending local Atlanta events, quietly ingratiating himself in the scene.

Hertrech “Hert” Eugene Jr. has been co-owner and president of Pain’s auto company, Nappy Boy Automotive, since it launched last year. The Orlando, Fla., native, who Road & Track magazine named the car world’s most important influencer in 2022, remembers his first impression of the singer as remarkably down-to-earth. “Pain wanted to check out what we call the burn yard, where we drift cars around and do burnouts,” he says, referring to a spin move that creates smoke and noise. “It was definitely weird to meet T-Pain, someone who I dressed as for Halloween in 2009 — fast-forward 10 years and he knows who I am.” Showing me a video from the first Nappy Boy-hosted drift event at Atlanta’s Caffeine & Octane raceway, Pain fans out over the various drivers, then points to himself behind the wheel of a souped-up pink race car as it drifts beside its competitors in a kind of chaotic ballet.

His entry into the gaming world was similarly unassuming. Though his former management had warned him not to publicize it, Pain had been active on Twitch since 2014, playing on- and off-stream with friends he’d made on the platform who were mostly chill about the fact that he was, well, T-Pain. One such friend was Mike Brew, who, after years of gaming together, began offering Pain advice about building out his channel into a professional organization; in 2021, that became Nappy Boy Gaming, with Brew as co-founder and president.

“Outside of music and music videos, my exposure to him was all on Twitch,” Brew says. “There was never a moment, seeing him on stream, where I was like, ‘Oh, God. This guy’s so full of himself.’ There are tons of artists that have come to Twitch since that are just terrible to watch because they’re so full of themselves. Meanwhile, Pain’s cracking jokes about himself, making relevant jokes about the streaming industry — he knows what he’s doing, and he’s shockingly humble about it.”

Pain and Brew had no connections to the gaming industry or to developers, so establishing the company felt like a scrappy startup, building custom servers and throwing DIY events, gradually earning the respect of the streaming community. “He’s recognized as an actual streamer,” Brew notes. “Not just as a musician trying to find a new revenue stream.” Even so, Matt Galle, one of Pain’s representatives at CAA, believes the singer’s side ventures have bolstered his tours. “When people were stuck inside during COVID, T-Pain was livestreaming daily,” he says. “People got to know him really well as a personality and human being and realized this is someone they believe in.”

Pain’s wisecracking charisma is part of his success on Twitch, but there’s also a decided “nerd recognize nerd” factor. These days he fields regular calls from rapper friends asking him how to get started on the platform. “Nope, I’m not telling you,” he says with a shrug. “I’m not trying to gate-keep, but I know you’re trying to get on there because you think I’m making a ton of money. I am! But still, it’s not like that. You should’ve got on that b-tch a decade ago then.” For all the rappers he names who use Twitch organically (Post Malone, Lupe Fiasco, Tee Grizzley), there are far more who see it as a come-up, though he stresses that the real nerds can sniff out the bullsh-t. “People have all these different ideas of how to make it cool, but it’s not about being cool,” he says. “It’s about gathering with like-minded people, being yourself and not having to conform to anything. The cool sh-t is, you don’t have to be cool.”

At the peak of his late-2000s hit-making, Pain believed that being his nerdy self would constitute career suicide. He still remembers reading blog posts in 2007 about Plies (who’d blown up the same year with the T-Pain duet “Shawty”) that mocked the rapper for having gone to college. “‘Nah, he ain’t no gangster, he went to college,’” Pain says, imitating the comments. “What’s that have to do with anything? You can be a killer and also know social studies.” The incident, he says, compelled him to dumb down the way he spoke; he began to drink more heavily and to spend money on the things that other rappers flaunted, desperate to fit the mold of late-2000s hip-hop stardom. He cackles remembering how the way he dressed would make onlookers think he was robbing his wife, Amber, who he married in 2003. Then he grows serious. “Eventually I found out that in doing that — being somebody that I wasn’t — anybody outside of the rap community just straight up thought I was stupid,” he admits. “It felt bad as sh-t. I didn’t want to be the stupid rapper that everybody thought I was going to be. I wanted to be better for my wife. I wanted to articulate myself. I had to change: to be who I really was and not who everybody wanted me to be.”

Pain’s nerdier passions have now found their way into his songs: For his latest solo single, the anthemic (and un-Auto-Tuned) “Dreaming,” he spent a month learning the 3D graphics software Blender in his spare time to animate the video, complete with exploding volcanoes, a Grand Theft Auto-style street scene and an impressively faithful rendering of himself. The breakneck recording pace of his hit-making prime has significantly slowed since going independent — but that’s because he prefers it that way. “You know the saying, ‘Find something you love and get paid for it’? I think whoever said that didn’t tell everybody, ‘Also, make sure you’re the boss,’” he says, clearly elated at his newfound ability to say no, or to simply do it his way. “That person also left out the part ‘Make sure it’s not your only income.’ Because if it is, you’re going to hate that thing that you loved in the end.”

These days, he uses his “entertainer side” to fund his hobbies, taking a few hours of work (a concert, a club appearance) and turning it into two weeks of fun. He still feels some residual burnout from two grueling decades in the industry, and to those who attribute his latest side projects to having fallen off musically, he has an unbothered reply: “Why stress myself out about doing all these red carpets,” he wonders, “when I could be playing video games in my drawers at home?”

It’s a cloudless 90-degree April day in the Coachella Valley, and T-Pain is dancing like no one is watching. In fact, a few hundred influencers are.

Dressed in their finest Y2K-flavored mesh and leather, the crowd is gathered to witness the singer twirl like a ballerina, hip-thrust like a Magic Mike extra and pop-lock like he has been taking notes from an old Darrin’s Dance Grooves DVD. Pain’s the sole headliner of the invite-only Celsius Cosmic Desert party, next door to the festival grounds on the first Friday of Coachella weekend, where Megan Fox, Halle Bailey and Barry Keoghan pose for pictures clutching dewy energy drink cans. Though the crowd for his 45-minute set skews more Gen Z than millennial, they appear to know every word to anthems like 2007’s “Bartender” or the 2008 Lil Wayne collaboration “Got Money.”

His double strand of Nappy Boy logo chains looks heavy, and his sneakers, it turns out, are one size too small. Still, the performance — his first of three he’ll do in the next 36 hours, both in and outside of the festival proper — is something of a milestone for an artist precisely 14 years older than the average attendee. “This is my first time even around Coachella,” he declares to the crowd, mopping his brow with a towel between songs. “I don’t know if that’s cool as f–k or sad as a motherf–ker!”

I’d been disabused of any expectations of backstage bacchanalia on the hourlong ride from Pain’s Palm Springs hotel to the windblown festival grounds, during which the singer sat quietly beside Amber, drinking Nesquik, relaxing to the sounds of smooth jazz and extolling the virtues of the new Call of Duty: Warzone mobile game with his bodyguard. It’s Amber’s birthday at midnight; later he’ll take her out for sushi along with the rest of the team, and tomorrow they’ll make a pit stop to grab ice cream before his set at the Revolve Festival in Palm Springs, which he’s headlining alongside Ludacris and a few more 2000s throwbacks (Sean Paul, Ying Yang Twins, Nina Sky). These days, that’s about as wild as it gets for Pain.

As the weekend’s prevailing Y2K aesthetic underlines, it’s a good time to be an icon of the 2000s charts. The period between 2007 and 2008 is generally considered the height of T-Pain’s career, the era when his voice was inescapable. But when he thinks about that time, “I remember forcing happiness,” he told me earlier in his basement. “I remember being drunk a lot. I remember going out to clubs in order to be happy because it wasn’t the studio, it wasn’t work.” He zeroes in on the moment when he found out that his second album, 2007’s Epiphany, had gone platinum. He was on tour at the time, making beats on the bus when someone brought the plaque in. “It was my first platinum album,” he recalls. “And I was like, ‘Let me finish this beat real quick.’ I didn’t really celebrate anything. Everybody else went out to celebrate for me.”

Pain’s current stage show — his Mansion in Wiscansin summer tour begins in May, after which he’ll join Pitbull’s Party After Dark tour in the fall — isn’t built around his latest release, On Top of the Covers, because the songs require at least a week of vocal rest between performances. But just before last Christmas, he partnered with YouTube to premiere an hourlong set of covers — some from the record, some unreleased — filmed live with a full band. Draped in a zebra-print bathrobe, Pain delivers what might be the best performance of his two-decade career, nailing heartfelt renditions of Gnarls Barkley’s “Crazy,” Sam Cooke’s “A Change Is Gonna Come” and Frank Sinatra’s “That’s Life,” the song that ignited his interest in recording the covers album in the first place. Listen closely to the lyrics and you can probably imagine why: “I’ve been a puppet, a pauper, a pirate, a poet, a pawn and a king/I’ve been up and down and over and out, and I know one thing/Each time I find myself flat on my face/I pick myself up and get back in the race.”

He directed the show top to bottom, from the arrangements to the lighting cues to the instructions for the band and backup singers. Pain banters a bit between songs, countering his bombshell performance with his usual self-effacing wisecracks. (“Tequila hit me a little harder than I thought it was going to. Should’ve ate and took a sh-t before this,” he quips after crushing “War Pigs.”) Eventually, he gets sincere.

“When you get into the music industry, you have this vision of arenas, big f–king crowds,” he tells the audience. “But over the years I’ve realized that we don’t get to connect with people, like, ever. We don’t really get to see in that mass crowd. The real connection is being able to see people. To me, this is superstardom.” He goes on to describe what drew him to musicianship as a kid. “One: When I started rapping in school, I started acquiring friends. People wanted to be around me for some reason. I wasn’t good, so I don’t know where the f–k that came from,” he jokes. “Two: The first song I learned to play on keyboard was ‘Lift Every Voice and Sing.’ That was my dad’s favorite song. I learned it in secret, and when I played it for him, his eyes lit up. I was like, ‘I want to do this all the time now.’”

The performance felt like the capstone to the past 10 years spent demonstrating his worth to an audience who’d largely dismissed him as a joke. Back in his underground sanctuary in Atlanta, he says he finally knows he has proved enough. “Looking back, I realized I didn’t have to prove anything,” he says, reclining in a gaming chair after an hour of restless pacing. “But I was so hungry for validation. I was so thirsty for people to like me.”

He’d been searching for that feeling of acceptance all his life, since his days as a self-described “smelly kid” who longed to sit with the cool kids when they were banging on the tables and rapping. “I just wanted people to like me. And I felt like, if you guys just knew how much I know music — if you looked past the Auto-Tune and you just heard me sing — I bet you’d like me.” But he doesn’t feel that way anymore. “It’s five people in this house that I need to like me: my wife, my kids, myself. That’s all I need. That’s all I ever needed. So, you know, suck a butt.”