T-Pain Celebrates Two Decades in Music: 5 Best Moments From the TP20 Tour’s First Show in NYC

T-Pain opened his show by announcing how he’d brought Florida to New York City. When the curtains were drawn up as he walked onto the stage, there were four classic Florida cars that he shipped up and positioned around many Florida palm trees to set the scene. He playfully joked, “It’s an expensive night for me. We didn’t have to bring all the cars from Florida, but we did.” Throughout the night, he highlighted aspects of Florida that he wanted to bring on his tour and how important they were to him.

T-Pain paid homage to his Florida roots by including many guests who consider Florida home such as Ski Mask the Slump God, 1900Rugrat, Ace Hood, and Denzel Curry. He playfully joked during his set when he told the crowd how he chose his guests — with his wife notably saying “that’s a lot of dudes” — and how, “per our marriage agreement, I’m not allowed to have any girls’ phone numbers.” Then JT from City Girls was added to the tour. He ensured that each guest had a short set to highlight many of their popular songs, including JT performing “JT Coming” and “OKAY.” The “Florida-adjacent” guest was Armani White, who ran onto the stage singing “Billie Ellish.”

T-Pain’s successful solo career also includes numerous hit collaborations, such as with Kanye West on “Good Life,” Akon on “I’m Sprung” and Chris Brown on “Kiss Kiss.” He performed these songs during his festival run earlier this summer, and fans were thrilled to see him bring them back for his TP20 Tour. When “Kiss Kiss” started playing, the crowd erupted with screams, knowing his hilarious dance moves would accompany the medley that he was about to perform.

T-Pain busted out the moves during his tour, with the crowd jumping and dancing in excitement alongside him. He playfully poked fun at being “almost 40,” joking that all the singing and dancing had pushed him “past his bedtime.” The crowd roared with excitement as he performed many popular songs he wasn’t originally part of — such as Drake’s “Rich Baby Daddy,” during which he threw it back and twerked to Sexyy Red’s chorus hook in his own T-Pain style, laughing along with the audience’s reaction. The concert was an endless supply of energy and laughs.

T-Pain sang “Stay With Me” by Sam Smith as he slowed down his set. The song marked a notable moment in his career, as it was part of his winning performance on NBC’s The Masked Singer in 2019. Many of the judges of the show had failed to guess his identity correctly, impressed by the raw vocal talent he showcased — without the Auto-Tune he had been primarily known for. As he belted out the lyrics on the Radio City Music Hall stage, fans turned on their phone flashlights and waved them in the air, cheering for him endlessly. He received a standing ovation and paused at the end of the performance to soak up the love fans were giving him.