Visit https://prizepicks.onelink.me/LME0/SHANNON and use code SHANNON and get $50 in lineups when you play your first $5 lineup!

Exclusive $45-off Carver Mat at https://on.auraframes.com/SHAYSHAY. Promo Code SHAYSHAY

Get harder, longer-lasting erections with Ro Sparks: $15 off first order of medication to get hard at https://ro.co/shayshay 

Shannon Sharpe sits down with T-Pain—one of the most influential rappers, era-defining hitmakers, visionary producers, streamers, and trendsetters who changed the course of music. Nearly two decades after “Rapper Turned Singer,” he reflects on his legacy while breaking down his new single, “Club Husband.” T-Pain opens with the lyrics, how the club scene has changed, and what it was like sneaking into clubs at 14, starting as a DJ, and becoming a regular despite his parents hating it. He talks about selling weed to friends, getting in trouble with police after school, and eventually dropping out and being expelled with only eight days of 8th grade left.

T-Pain explains why “stealing dudes’ girls” has always existed in clubs, sharing a wild story from London where he stole a girl, confronted a man named Tiny—three times bigger than Shannon—and ended up throwing money that led to a fight. He jokes that a man can even find a husband in the club as he and Shannon debate the best ways to meet women. T-Pain opens up about meeting his wife, proposing after three months, and still having the first video of them together.

He breaks down “Club Husband,” “Buy You a Drink,” and the etiquette of buying women drinks as he and Shannon go back and forth about helping people. T-Pain reveals how he had to pay Lil Scrappy and Lil Jon for “Buy You a Drink”, and why he hates that “Club Husband” blew up on TikTok, and how someone stole an unreleased version from his stream and tried to profit from it. They discuss Drea Michelle, Draylen Green, the new generation discovering T-Pain, and the 20th anniversary of the rapper-singer era.

T-Pain reflects on industry lessons—how “no one is your brother,” getting regifted client gifts, artists wanting him on features but not in videos. He explains why he sold his catalog, how HarbourView Equity Partners partnered with him, and how he reinvested: a 50-square building for his company, a plane, and simple black shirts for his wife. He admits mistakes from early fame, like buying a Bugatti and a chain before losing his house, investing in bad ideas, and being robbed by people around him—lessons that made him obsessive about his finances.

He shares memories of inventing pre-sagged pants with his grandfather. Explaining why he creates all his music on Twitch, and why he embraced Auto-Tune like Roger Troutman before proving he could really sing through covers. T-Pain reveals dream collaborations like André 3000, why he’d never do the Super Bowl halftime show, and how he learned to stop craving recognition for songs he wrote. He talks about still doing T-Mixes, almost canceling The Masked Singer three days before filming, and performing blind every night because he couldn’t see in the costume.

In the end, T-Pain says his proudest accomplishment isn’t awards or hits—it’s that his wife loves him, and his kids don’t hate him. Everything he does includes them, and that’s what matters most.

See omnystudio.com/listener for privacy information.