Florida rapper T-Pain shocked the world when he won the first season of the singing competition series, “The Masked Singer.”
In 2019, he left the audience and viewers at home frazzled for weeks, wondering if it was really him under the guise of “The Monster” costume.
But the victory almost never happened. The Grammy winner nearly walked away before the competition even began and has now revealed the unexpected reason he signed on in the first place.
T-Pain showcased his powerful, natural singing voice without his signature Auto-Tune throughout the season.
He performed hit songs like Sam Smith’s “Stay with Me,” the “One Tree Hill” theme song, “I Don’t Want to Be” by Gavin DeGraw, and closed the finale with Montell Jordan’s “This Is How We Do It.”
The wild part? T-Pain now claims he ended up on “The Masked Singer” by accident.
When asked why he decided to do the show, the “Buy u a Drank” artist confessed, “I didn’t. I was drunk.”
He told rapper T.I. on the “ExpediTIously with Tip T.I. Harris” next time, “Tell me to stop drinking on conference calls.”
Afterward, he regretted it and tried to back out “three days before” the show was set to tape because he thought the show sounded ridiculous.
He then admitted, “Because I saw it on paper and I was like, ‘Oh, this is going to be awful. This is going to be stupid as hell. I don’t want to do this.'”
T-Pain mistakenly believed that if viewers or the judges figured out who he was, the show would kick him off.
He thought his voice was so recognizable that he assumed he’d be eliminated almost instantly.
“But I’ve had people tell me, ‘I did not recognize you without hearing you in AutoTune.’ It’s weird as hell,” T-Pain shared.
Instead, many people didn’t recognize him without AutoTune, and he went on to win the entire competition.
In the end, the singer beat out Donny Osmond as The Peacock and Gladys Knight as the Bee, who placed in second and third places, respectively.
Footage of T-Pain’s latest remarks hit the same internet that erupts over his natural vocals. Yet supporters of him and “The Masked Singer” say his appearance did wonders to resurrect his career and years of stepping back to make more money gaming.
“It’s crazy. He felt that way. I felt like it did his career a service. He let people know he had real talent, not just the machine,” said one Facebook user.
Another said, “I knew T-Pain was the monster [in the] first episode! Idk how you lasted so long lol”
A third individual noticed, “You have a very distinct cadence. I knew it as soon as I heard it and told my son. We’ve been fans since Rappa Ternt Sanga.”
Chiming in with jokes about his drunken response, one person added, “Not blaming it on the alcohol.”
Another said, “To this day, I still randomly play T-Pain’s performance of ‘Stay With Me.’ He made me like his version of the song as much as Sam Smith’s. He is SIGNIFICANTLY downplaying how dope he was on that show, and he earned that win. Judges were crying through his performances. I’ve seen him sing live, but he was so much more polished on ‘Masked Singer.’”
Following his victory on the Fox series, T-Pain capitalized on his renewed momentum.
He teamed up with Kehlani for the Western-inspired video for “I Like Dat,” a fresh spin on his 2007 hit “Buy U a Drank.” The song peaked at No. 12 on Billboard’s Mainstream R&B/Hip-Hop Airplay chart.
He later collaborated with pop star Meghan Trainor on “Been Like This.”
Most recently, he also lent his vocals to rapper Glo Rilla’s “I Luv Her.” The collaboration reminded fans of “Shawty” with Plies and “She Got It” with 2 Pistols, two early-2000s hits that cemented T-Pain’s early career.
T-Pain received the 2025 BMI President’s Award in recognition of his two-decade career that helped redefine modern music through his pioneering use of Auto-Tune.
His signature sound has not only defined his career but also sparked some of its biggest controversies.
He and Usher publicly ended their long-running Auto-Tune dispute after T-Pain revealed that Usher once told him he had messed up music, a comment T-Pain said contributed to years of depression.
Although Usher said they had resolved the issue privately, T-Pain initially disputed the claim. The two ultimately reunited onstage at a Dave Chappelle show in Atlanta in 2021. They embraced and declared there was no bad blood, though some fans questioned whether Usher had ever truly apologized.
Beyond music, he has expanded into gaming, streaming, and business ventures, which generate more income than his song royalties.
