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Skip Bayless has made plenty of enemies over the course of his career as a Hot Take Artist, but he’s also found a somewhat unexpected friend in the form of Lil Wayne—a relationship that apparently stems from their mutual respect for Steph Curry before he cemented himself as one of the deadliest scorers in NBA history.
The two men have known each other for close to 15 years, and the rapper appeared on First Take multiple times when Bayless was still hosting the show with Stephen A. Smith at ESPN. After Shannon Sharpe announced he was leaving Undisputed, FS1 announced Lil Wayne would become a regular guest and even got him to record a new theme song for the show.
Bayless is close with the hip-hop legend to the point where he attempted to recruit the New Orleans native to give Ja Morant some much-needed guidance in the wake of the multiple gun incidents that defined his tumultuous season in 2022. I think most people are aware they’re pretty tight, but there’s also a good chance you don’t know why they’re friends in the first place.
The duo recently chatted with GQ and shed some light on the first time they crossed paths when Weezy headed to the ESPN campus in Bristol in 2009 while touring. Bayless said their initial meeting transpired a couple of months before the NBA Draft that year, and he realized they’d get along after they bonded over their shared admiration for a lanky guard who’d made a name for himself at Davidson:
“I knew your work, but I didn’t know you, and I didn’t know your depth of sports knowledge! But we were coming up to Steph Curry’s draft, and I was a Steph Curry fan at Davidson.
You shocked me, in a good way, because you said you would take Steph over Blake Griffin! Everybody at ESPN was head over heels with Blake Griffin because he could jump out of the gym…
That was the first time I said, “Woo, you know your stuff!” The point is—they say I don’t suffer fools, I can’t talk sports with many people—he was the one person in the world that I would choose to talk sports or life with. It started to take shape that day.”
What a world.