The ringtone rap era still feels like the wildest fever dream in hip-hop. Like, did it really happen? Yes, it did. By the mid-2000s, song-buying options had dramatically expanded to include not just CDs but also legal downloads, with iTunes monopolizing the digital market and record labels making billions off turning the catchiest parts of their artists’ singles into 99-cent ringtones—a step up from the sparse polyphonic MIDI tunes of the past. And a 23-year-old Tallahassee Pain was widely recognized as the campy, charismatic maestro of the pitch-correction software Auto-Tune; even if he didn’t invent it, he was largely responsible for its newfound prevalence in pop, and there was no turning back. Every rap hook T-Pain crooned over—alongside Plies, E-40, Kanye West, and even Flo Rida—was gilded, contributing to his title as the de facto ringtone king.

The coronation was, of course, fleeting. T-Pain’s early ballads, “I’m Sprung” and “I’m N Luv (Wit a Stripper),” sold a staggering 6.7 million ringtones combined in 2005, the same year Billboard began tracking digital download sales and right before the RIAA introduced gold and platinum certification for ringtones. Those ringtone sales significantly outpaced both his album sales and digital downloads. (His 2005 debut, Rappa Ternt Sanga, went gold but never platinum.) “I had people at Jive tell me they didn’t believe in my product and let me know that they didn’t too much care,” T-Pain said at the time. “But selling 6.7 million ringtones… changed their minds.” By the end of 2007, he’d earned his first and only No. 1 hit as a solo artist and the year’s best-selling ringtone for his bleary breakup elegy “Buy U a Drank (Shawty Snappin’),” while the song’s parent album, Epiphany, struggled to achieve gold status.

Even in a rapidly changing digital landscape, physical album sales were still the benchmark of a hit, and T-Pain couldn’t survive on just making club gospel for millennial flip phones. Though Rappa Ternt Sanga had felt like electro-soul innovation, pop listeners weary of the robot sound were coming to see T-Pain less as a trendsetter and more as a gimmick without a real voice. With his second album, Epiphany, he hoped to change people’s minds. “I’ve made club songs, and I’ve made radio songs, and I’ve made the car songs. These songs are T-Pain songs,” he told the Associated Press ahead of the album’s June 2007 release. “If people like this album, that means they like me as a person.”

Like Michael Bay pumping out Pearl Harbor after Armageddon after Bad Boys, T-Pain leaned even more heavily into Auto-Tune on Epiphany than on his debut. (“I’m not gonna change my style because other people are starting to overuse it. Like, that’s just weird,” he later reasoned.) If T-Pain wanted listeners to take him seriously as an artist, then choosing Auto-Tune wasn’t exactly the safest bet. Owning it turned out to be his greatest short-term challenge and ultimate triumph, placing him in extremely rarefied air as both a novelty act and a cult-pop trailblazer. Epiphany effectively patented his computerized soul technique with a melange of cathartic party anthems, lovers’ ballads, and a hint of country, proving his success wasn’t just a one-time break.

The precision so often attributed solely to tech is very much a product of T-Pain’s naturally sleek vocals. The man is the machine. Yet despite a No. 1 debut on the pop charts—Epiphany landed one spot ahead of Rihanna’s era-defining third album, Good Girl Gone Bad—it was more of a commercial than a spiritual win for T-Pain. His songs were mainly fun, unobjectionable tunes about bar-hopping and looking for love in the club; mainstream R&B was moving in a different, more heartless direction. He was now competing with blunt-bob-era RiRi and The-Dream, who had just skyrocketed to fame writing the decade’s most glutinous pop hits (including 2007’s two biggest singles) and would soon claim T-Pain’s title as pop-R&B’s most unserious hitmaker.

In retrospect, what dates Epiphany the most isn’t Auto-Tune but rather the snap sound and references to millennial regalia like belly button chains. It’s T-Pain’s musicality that elevates the material beyond the nostalgia value of, say, a kitschy Flo Rida tune. In T-Pain’s hands, a song like “Buy U a Drank” feels like both an alien opera and a romantic limerick. He charms an anonymous woman in the club over pinging synths—a hallmark of snap—dropping humble lines like, “I’m T-Pain. You know me.” Snap music had newly emerged out of Buckhead, Atlanta, as the carefree, shinier offshoot of crunk, providing a perfect template for ringtones: tinny, 808-driven minimalist tracks that could easily be clipped into 5- to 30-second mobile earworms. While T-Pain was busy yassifying pop, snap tracks like Dem Franchize Boyz’s “Lean Wit It, Rock Wit It” and D4L’s “Laffy Taffy” easily cracked the Top 10. Jive Records A&R Mickey “MeMpHiTz” Wright saw an opening for a smash, prompting T-Pain to begrudgingly record “Buy U A Drank,” featuring Yung Joc, then Atlanta’s foremost ringtone rapper.

Though T-Pain was initially hesitant to adopt a sound he correctly assumed was a fad, snap music clearly suited his style—a sugary, Auto-Tune-drenched trill that sounded like Megatron singing freakishly sweet love songs. Again, on the album’s second single, “Bartender,” synths gleaming like starlight, he recounts a night out with the brevity of a blues singer, parroting his own lines: “Broke up with my girl last night/So I went to the club.” So flawlessly does Akon harmonize with T-Pain on the hook that it’s easy to forget he sings the third verse (many DJs likely cut the song off before then), playing a sober wingman requesting T-Pain’s permission to bounce with a new friend.

In singing about the euphoria and delirium of nightlife, T-Pain nods to his Tallahassee roots on the early album cut “Church,” a countrified fight song filled with banjos and handclaps, and “Show U How,” which feels like the soundtrack to a rodeo or praise dance. He deploys his rap alter ego, Teddy Penderazdoun, to pursue the scarlet-letter woman in town, playing off the ho-into-a-housewife trope, annoyingly. But it’s also… sweet? “Tell ’em kiss yo ass/’Cause at the end of the day, you got a place to/Lay down and let me lay with you,” he sings. All part of his life’s work. His rap personas (the other one on the album is Teddy Verseti) exist mainly to show his versatility, and he is entertaining and often dexterous as a lyricist but much better at bellowing sweet nothings than tough talk.

The party vibe in T-Pain’s music is sometimes thick to the point of overshadowing the fun. The darker side of his debauchery is “Tipsy,” where the mood feels coercive, to say the least: “I knew you wouldn’t be the freak that you are unless you tipsy,” he sings (in a Juvenile-esque lower register), proving that the booze-and-a-good-time objective has an outer limit. As T-Pain explains it, though, he celebrates a lot because drinking and merriment feel genuinely restorative, and that’s the way of the South. “I think people relate to my songs more because I’m not trying to be overly clever. It’s kinda just normal conversation,” he told NPR in 2014. “It’s just, ‘Listen. Here’s the situation. Here’s a melody to it. You like it? You don’t? Here it is.’”

Epiphany is full of odd surprises. “Time Machine” is a delightfully weird sci-fi ballad in which T-Pain portrays a robot named Tebunon Pedalophagis from Planet Teleguston, singing like a sad Iron Giant about returning to simpler times before his career took off: “Illudium PU-36 explosive space modulator/Goin’ on a trip, I’ll be back/Homeboy, I’ll see you later,” he laments, allowing himself to dream, Auto-Tune on the zero-est setting. (Planet Teleguston begs for a visual treatment.) The track is, of course, quickly followed by a sensual homage to Pilates-toned abs, “Yo Stomach,” the kind of absurd T-Pain song you can probably hear before actually listening to it. There, and on pleasure-seeking records like “69” (no guessing what that’s about) and “Put It Down,” his vocal texture is both smooth and gritty, like a pitcher of lemonade with sugar grains at the bottom.

His tone is the infrastructure that helps his Auto-Tuned voice authentically synthesize the sounds of heartbreak and lust. Musician and writer Jace Clayton demonstrated the nuances of T-Pain’s singing in an episode of the Netflix docu-series, This Is Pop, praising T-Pain’s blend of melisma and machinery and comparing his algorithmic coos on “I’m Sprung” to Whitney Houston’s dramatic runs on “I Will Always Love You”—both of which are rooted in gospel.

In recent years, T-Pain has shared a story about Kanye mocking his bad ideas when he worked as a consultant on the 808s & Heartbreak studio sessions. Within Ye’s bullying is a valid point: Sometimes, T-Pain does too much. While it’s fun to hear him over a greasy, industrial dancehall track like “Shottas,” it’s also T-Pain rapping in patois. Then there’s the operatic “Suicide,” a stark, acoustic-heavy public service announcement where he sings from the perspective of a guy whose partner has contracted HIV. T-Pain being serious (while singing la-la-la) is a hard sell, though his vocals sound beautifully coarse as he belts, “Stuck on my ass/I been drinking for days.” Far more heartfelt is “Sounds Bad,” an earnest palate cleanser about making the best of hard times where he ditches the ultra-processed filter and sings over live, jovial keys and percussion, lamenting: “First of the month. Check late. Got nothing to do. I’ma roll me a blunt. Got drank.” T-Pain produced the majority of the album (same as his debut); you wonder if he might have benefited from collaborators who could have gently steered him away from his goofiest impulses without stifling his creativity.

In the years since Epiphany’s release, T-Pain’s Rocky Horror-like redemption story has become pop lore. Jay-Z tried to kill Auto-Tune. Ringtones died for real. Usher sweetly told T-Pain he ruined music. T-Pain spiraled into depression, only to eventually receive belated accolades for singing, rapping, and producing some of the world’s greatest club bangers—songs that now evoke the revelry and purity of the pre-social media era. T-Pain made rap more melodic, but it would take over two decades for him to receive proper credit, leaving the door wide open for an artist like Kanye to shamelessly co-opt T-Pain’s formula, inspiring every singing rapper and rapping singer on the planet (The-Dream, Drake, Future) to enter their emo-villain era. Epiphany reached multi-platinum status only in 2022, bolstered by T-Pain’s victory on The Masked Singer and his revelatory NPR Tiny Desk performance.

Most of us should know by now that T-Pain can actually sing. And yet, there are still people in this world who don’t believe it. As casual listeners came to appreciate his natural vocal chops over the years, their sense of shock at the discovery only frustrated him more. “Like, really?” he asked in disbelief in This Is Pop. “Did y’all think my whole career was based off of… software?” Well, yes. T-Pain didn’t have the mindset of a mad genius or the huge ego required to promote his artistry with the gravitas it deserved. Only in hindsight did he realize his humility was kind of a mistake. Epiphany is a timestamp of his sound and influence that legitimizes his artistry and confirms what he’s been trying to tell us all along.

Additional research by Deirdre McCabe Nolan.