This story is over 5 years old.

Friday Thinks With Luke Winkie

A History of Skip Bayless Interacting with Rappers on ESPN's 'First Take'

Watch as Skip Bayless awkwardly navigates conversations with Lil Wayne, Nelly, 2 Chainz, T.I., and more!

For a self-respecting, culturally-involved human being, I watch an awful lot of ESPN’s First Take. I honestly don’t know why. If you’re not sure what First Take is, picture an extremely banal debate-driven sports talk show, led by a mannequin of a humainoid named Skip Bayless. Skip Bayless is the undisputed champion of yelling desperately controversial sports opinions on TV, and frankly seems kind of racist. Not racist as in "Wears a KKK hood," more like "racist" in that a lot of the show's action involves pointing out that he has no cultural understanding of anyone who is not an old white dude from Oklahoma, and despite his numerous attempts to correct this, is physically incapable of doing so.


Skip Bayless’s pseudo-racism is buoyed by one of First Take’s chief recurring features, which is that rappers are perennially brought onto the show as guests to talk to Skip Bayless about sports. This is probably due to some executive somewhere deciding that the show needs to appeal to a younger, more urban audience, because there is nothing less urban than Skip Bayless, a 61-year old white dude from Oklahoma who looks like a cross between a muppet and a corpse. Who is, again, sort of racist. This has lead to a number of beautiful moments where Skip Bayless has had to converse with a rapper. Here are some of them.


This actually only happened just yesterday, and Skip Bayless immediately said “Fiddy” so we know that he “gets it.” I’m actually just happy that 50 Cent still has enough social capital to book an appearance on basic cable. Anyways, 50 Cent actually knows a lot about boxing, and this is actually a pretty good interview if you like hearing Curtis Jackson speak softly and eloquently.


In this video 2 Chainz gives Skip Bayless a chain and he is quickly dubbed “1 Chain.” When Skip tries to sit back down, the chain hits the table. For a brief moment there is nothing but apocalyptic fear in Skip’s eyes.


“I love hearing this provocative theory from the master of trash-talk himself” - Skip Bayless on Lil Wayne. This is also an important moment in First Take history because this is the day that Skip Bayless considers himself and Lil Wayne to be friends. When Lil Wayne got kicked out of the NBA Finals game in Oklahoma City last year, Skip Bayless said on national TV with pure honesty that Lil Wayne should’ve texted him and he would’ve sorted it out. Sometimes I like to think about Skip Bayless and Lil Wayne texting each other when I’m sad.



The only thing reassuring about Wale being on First Take is it gives me hope that maybe someday Rick Ross and Skip Bayless will drink expensive drinks and talk about the Miami Heat.


Yes, Bun B did a freestyle for First Take, at which point Skip Bayless said this:

“Allow me to say, Bun B just rapped Wale under the table.” At which point host Cari Champion sighs a heavy, disgruntled, “Oh gosh…” Skip Bayless is such a beautiful presence in all of our lives and we are a blessed nation that ESPN pays him to say words.


For the first few minutes of this segment, Stephen A. Smith and T.I. go back and forth respectfully and passionately, talking about who they consider to be the greatest rapper of all time. Then they ask Skip Bayless who his favorite rapper is and one of the most beautiful moments of television history happens. “Skip Bayless, you listen to Biggie?” “You better believe I do.” Also “My friend Lil Wayne belongs in this conversation.”


In this video Skip Bayless says Nelly is one of the top 10 rappers of the 21st century. It is the crown jewel of the Skip Bayless talking to/about rappers. I had never seen a shooting star before, and then I saw Skip Bayless talking to Nelly on television.

Luke Winkie could beat Skip Bayless in a fight. He's on Twitter - @luke_winkie