Lil Wayne and Skip Bayless on Their Unlikely Friendship: ‘No One I’d Rather Talk Sports or Life With’

Skip Bayless wraps up another dynamic episode of his Fox Sports 1 show, Undisputed. This episode, like every Friday since late August, featured his friend Lil Wayne. The sports debate segment highlighted their seamless rapport, an on-air chemistry that has been brewing for years.

After the show, Bayless, 71, and Wayne, 41, connect with PEOPLE over Zoom. It’s immediately clear how deep their bond runs, forged over the fifteen years since Wayne first appeared on Bayless’ former ESPN show, First Take.

“Right away, he caught my ear,” Bayless reminisces about their first encounter. “In our pre-show meeting, we talked about Steph Curry and Blake Griffin, who were then about to be drafted by the NBA. He pleasantly shocked me by saying that he thought Steph was better than Blake, something I had believed and people at ESPN thought I was out of my mind about. I said, ‘This man really knows sports.'”

Wayne’s depth of sports knowledge continues to impress Bayless. “I don’t usually indulge others talking sports because I think I know a lot more than they do, so I don’t want to waste my time. But there’s no man on earth I would rather talk sports or life with than this man. Even though we come from sort of opposite ends of the earth, we’re very much alike in how we see sports and, in many ways, how we see life.”

Their friendship isn’t just about sports. Wayne, whose full name is Dwayne Michael Carter, Jr., and Bayless share insights into their personal lives, their long-running careers, and even delve into pop culture phenomena like the “Taylor Swift effect.”

“It’s crazy. Kansas City Swifties,” Wayne laughs. “I couldn’t believe that we actually tapped into the Taylor Swift subject. She is definitely an artist for her fans. The Swifties, or whatever you want to call them, she is for them.”

Bayless chimes in with admiration for Swift’s dedication, drawing parallels to his own work ethic. Both he and Wayne recognize the importance of connecting with their audiences, a principle that has fortified their respective careers.

As they reflect on their collaboration on Undisputed, Wayne shares his learning curve. “I’m learning how to work on the fly, just because things can change. I’m also learning how to be critically honest and not offensive.”

Bayless echoes this sentiment, emphasizing the importance of chemistry. “What I’m learning is his rhythms on television, what he is most comfortable doing, what he responds to best. It just takes repetitions. You can’t fake it. You can’t rehearse it. You just have to keep doing it.”

Their off-air friendship is equally significant. Bayless recounts his and his wife Ernestine’s visits to Wayne’s house. “Sometimes we just stand in the kitchen, sometimes we sit on the couch, sometimes we go out on the back porch. The last time we were there, we were on the back porch, and I looked down and we had been talking for four hours straight with no bathroom breaks, no drink, no food, no nothing.”

Wayne’s journey, from his grandmother instilling a love for sports to his rise in the music industry, mirrors Bayless’ dedication to sports journalism. “There is the cliché of ‘We started from the bottom,'” Wayne notes. “The similarity to me is his dedication to what he loved from such a young age. I had to be obsessive because my mom didn’t even want me to rap. She was just like, ‘You’re too smart. You’re going to be a lawyer, a doctor. You’re not about to make words rhyme.'”

Their mutual respect is evident in their conversations. Bayless marvels at Wayne’s creative process and considers him the greatest living rapper. “I think he’s the GOAT. I think he’s the greatest living rapper. We could debate it all day and all night. I’m biased, but I got hooked on Carter III, just as we were getting to know each other.”

Wayne reflects on his music’s impact, particularly the song “How to Love.” “I’ve never gotten a response the way I do from that song. The response I get from that song is totally different. Everybody has a different story. It can be everybody, I mean, even [49ers coach] Kyle [Shanahan]. They all have a different reason why that song touches them.”

Their bond transcends professional boundaries, blending into personal admiration and shared moments of inspiration. Whether it’s crafting show intros or debating sports legends, Wayne and Bayless have created a unique friendship that continues to flourish.

As they look to the future, Bayless dreams of turning his screenplay into a film, with Wayne starring in it. “For me, I hope and dream every day. I just want to be better every day,” Wayne says.

Bayless concludes, “These times in my life are the most special, meaningful times. You’re doing something that counts. It matters to me because I learn and I laugh and I share in ways I just don’t often have time or the opportunity to do. We don’t look at our phone. It’s beautiful.”

In the end, it’s clear: no one they’d rather talk sports or life with than each other.