Skip Bayless and Lil Wayne have been close friends for a minute, and during a recent Q&A, the host opened up with a little bit of backstory. Around the 6:05-minute mark of the video, Skip Bayless fields a question about his relationship with Lil Wayne, and the extent to which it has since blossomed. “2008, I’m working in Bristol, Connecticut at ESPN,” reflects Skip, setting the tone. “There was a rapper that I was ironically a big fan of, thanks to the album Country Grammar. His name was Nelly. Nelly’s people got a hold of my people, and said that Nelly wanted to come on First Take and debate me face to face, head to head. I was like, let’s do it man! Many of the executives at ESPN were not down with this premise. It never happened on live TV that we would have a rapper. Oh My God, what might he do?“
Skip proceeds to praise Nelly’s appearance, dubbing him “sensational.” “We sparred and we pushed and we shoved verbally, and we had a great time…He’s been fairly regularly a guest on our show here in LA on “Undisputed,” and I text with him often.” Though he and Nelly recently had an argument over something most likely sports-related, Skip feels like they’ll ultimately be okay. Yet the path to Weezy continues. “This involved my wife Ernestine,” says Skip, returning to the task at hand. “She likes to book people on TV shows…She said, if Nelly worked, let’s get other rappers. We tried Bow Wow – not the greatest idea.” Eventually, Ernestine suggested Lil Wayne, who Skip revered to a Godlike level.
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“Lil Wayne did it!” reveals Skip. “After the show, Lil Wayne actually took me into [his tour bus] into a recording studio that he has built into the bus. It was just the coolest thing that ever happened to me.” After praising Weezy’s sports knowledge and passion, Skip dropped off the quintessential bromance phrase: “I love you man!” “We talk fairly regularly, we text all the time,” he continues, before sharing a tale of Weezy’s generosity.
Upon discovering that his friend Craig Humphries’ son Sam was diagnosed with testicular cancer (at the age of 21), Weezy held it down for the young man, encouraging him during a twenty-minute phone call. Skip also notes that Weezy had a laugh at having another “white fan,” joking that “Wayne has done whole concerts where he couldn’t see a single black face, it was all white faces, and he loves that. He’s the coolest in his racial view out of anybody I’ve ever been around.”
Who’d have thought that Skip Bayless and Lil Wayne would have such a solid friendship?