T-Pain’s Party at Jacobs Pavilion Wore Me Out, and I Loved It

T-Pain stopping in your city is a lot like Santa Claus coming to town. Like Claus, T-Pain is also a jolly man in a lavish suit. But instead of gifting children toys, he puts smiles on the faces of drunk millennials with his bag of goodies that’s actually just 20 years’ worth of club bangers. It’s unfortunate if you missed TP20: Celebrating 20 Years of T-Pain at Jacob’s Pavilion on Wednesday night, because I won’t be able to give you the full scope of the entire evening; that would be like trying to encapsulate a night at the club. Nearly impossible. But I’ll give it a shot.

I started the night gently elbowing my way to the front of the pit, but ultimately, trying to see through the weed fog down front was taking away from my T-Pain experience — I needed a crystal clear view of the aforementioned suit and couldn’t miss his now signature twirling move (born from his Coachella performance earlier this year). So, I Houdini-ed my way to a clearer spot and fresher air. Now, I had a much better view of the stage, which featured two giant “X’s” (again, celebrating 20 years). An audio clip starts the set. It’s a man with a British accent citing some sort of satire-adjacent spoken word about manifestation, not giving up, and if you’ve been doing something for 20 years, “you must be doing it right.” Exactly one second later, and we have eyes on Pain, and he’s sporting a leprechaun green suit dripping in crystals, and a pair of white sunglasses. He’s immediately busting out high-energy choreography alongside his backup dancers, who are decked out in black sparkly suits, and one gorgeous female dancer in a tight dress trimmed with fur.

Pain opened his set with 2007’s “Shawty” because, of course, and everyone goes completely nuts. But the thing is, everyone steadily goes nuts the entire night. Name a smash hit from the 2010s, and it belongs to Pain in some way (it’s his, he’s featured on it, he wrote it, etc.). Pain makes jokes throughout the night about the difficulty of putting the set list together, but honestly, he could have done it a million different ways, and the result would have been the same: wall-to-wall bangers and a thrilled, sold-out crowd.

At one point, he moves into what I’m calling his problematic section of the night. Pretty much in a row, he performs his verses only from Kanye West’s “I’m Good,” R. Kelly’s “I’m a Flirt” (remix), and Chris Brown’s “Kiss Kiss.” From his perspective, it’s got to be frustrating when some of your former co-workers steadily ruin your monster hits by being, well, monsters. You could choose to see Pain’s performing snippets from these once beloved bops as tone-deaf, or you could think of it as him reclaiming his part in them. That’s the version I went with.

By the second half of the night, Pain slips into something more comfortable (basketball shorts, t-shirt), and we get what felt like the complete songs for “Bartender” and “In Love With A Stripper,” which were paired beautifully with animated stripper graphics on the screens behind Pain. From here were some of the best treats of the night, with him performing a couple of tracks from “On Top of the Covers,” an incredible album of all covers he released in 2023 (Black Sabbath’s “War Pigs” and Journey’s “Don’t Stop Believin’”). I was not-so-secretly hoping this would happen. I listened to that cover album on loop that year. The man can take literally any song, and his soulful, raspy vocals make it a thousand times better. If you only think of T-Pain as the auto-tune guy in the top hat who wants to buy you a drank, you are missing out on one of music’s most multifaceted artists. In fact, you may be surprised to learn he’s the secret penman behind some of your favorite country songs. In 2024, Pain revealed that he removed his credits from country songs he’s written for other artists, thanks to the racism that runs particularly rampant in the country genre. “I’ll just take the check. Don’t put me on that shit,” he explained in a TikTok. Pain also gave us Joan Jett’s “I Love Rock and Roll” and Lenny Kravitz’s version of “American Woman” during this rock-ish section, by the way, which was another standout moment for me.

Moving back into club fun and 2010s nostalgia, big boat graphics appear on the screen next, and he surprises his boozy crowd with The Lonely Island’s 2009 “I’m on a Boat.” The party ramps up harder at this point because it’s nearing its end, and it seems Pain wants to give everyone their money’s worth. LMAFO’s “Shots” mashes into Flo Rida’s “Low” before moving into “All I Do Is Win.” And just like that, the low-key chaotic evening packed with every song you forgot you loved is over, and you can’t wait for Pain to slide down Cleveland’s chimney again next year (hopefully).