T-Pain has a lot of regrets throughout his career but purchasing his notorious “Big Ass Chain” for well over six figures seems to be the one he can’t get over.

The “Buy U A Drank” singer sat down with Oliver Tree for an episode of his Nappy Boy Radio Podcast earlier in January where he explained what pushed him to cop the ridiculous $400,000 chain, which he still has.



“One of my biggest regrets but I keep it around to remind myself,” Pain said. “Actually now [it’s worth] probably like $200,000 at the most. Just, price just went down — the price of gold and diamonds aren’t what they used to be.

“Somebody was on the side of the stage at one of my shows and they said, ‘I bet you won’t get a big ass chain that says, ‘Big Ass Chain.’ And I said, ‘You don’t know how much fuckin money I got right now. So don’t fuckin try me.’

He continued: “I don’t know the guy, didn’t get his number, never seen him again and went and spent money on this chain to prove to this stranger that I would do it.”

T-Pain made the egriogious purchase for the bedazzled chain from the famous Atlanta-based jeweler Icebox in 2009. According to Hatton-Jewellers, the hefty “Big Ass Chain” weighs over 10 pounds and is made from yellow and white gold while boasting a robust 197 carats of diamonds.

In his mainstream prime throughout the second half of the 2000s, T-Pain features were heavily in demand as artists wanted to sprinkle in his unique AutoTuned twang to add another element to their hits.

So it’s safe to assume the Florida-bred artist had more money pouring in than he could account for. In another podcast episode with Taylor Bennett last year, T-Pain revealed he had so much money at one point he started charging rare cars in exchange for guest verses and hooks.

“I started charging n-ggas cars for songs,” he said. “It came to a point where I had enough money and n-ggas was like, ‘We need a hook.’ Hey, look, it’s a ’72 Impala that I want. I don’t even want a new car, bro, go get me a old school and I’ll do this hook for you tonight.”



T-Pain’s huge financial security might be the reason he decided to try his hand at being a Peloton instructor last year.

Looking to crossover into the fitness space, he took to his Instagram in August to share a video of himself riding the stationary bicycle and barking out instructions to fellow riders. Peloton seemed impressed by the audition, sharing it on the company’s official TikTok page.