Skip Bayless’ Best Rapper Debates [Video]

Photos courtesy of Joe Faraoni/ESPN

[*Editor's Note: This article originally appears in XXL's March 2012 issue, on stands now]

Skip Bayless loves the fact that rappers are such dedicated sports fans. But that doesn’t stop the notoriously outspoken TV personality (and former newspaperman at the Los Angeles Times and Dallas Times Herald) from trying to tear guest MCs apart when they challenge his sports opinions during ESPN2’s daily morning show First Take. Over the past few years, Bayless has deliberated with some of hip-hop’s finest, including Lil Wayne (a three-time guest), Wale, Nelly, Fabolous, Bow Wow and LL Cool, about everything from LeBron James’s greatness to Floyd Mayweather Jr.’s dedication. Most recently, he and Joe Budden went at it after the two had an exchange on Twitter about the MC’s sports acumen.

Here, Bayless talks to XXL about his respect for Weezy, getting under LL’s skin and staying connected with rappers after he debates them. Ball so hard.

Who was the toughest rapper to debate sports with live on ESPN?

Lil Wayne [has] the deepest [knowledge] and maybe the most sports savvy of anybody we’ve had in, as far as knowing a lot about all sports and having very provocative, profound opinions about them. You have to listen carefully, because he’s not going to shout at you, but his words are powerful. I’ve walked back to his bus all three times with him [after each show appearance], and he’s just walking on air. I don’t think it’s because he took something before the show, either. It’s a natural high. He gets off on the forum we have because he knows it’s live TV.

How would you evaluate some of the other MCs that tried to contest you?

Nelly came out swinging—verbally, not physically—and was not intimidated. He’s the first one who told me, “This is straight barbershop.” LL and Wale, they came out firing. Wale is high-octane, man. He is going to be loud barbershop and just come with knee-jerk, off-the-cuff, from-the-heart opinions. He always comes in saying he’s going to set me straight about LeBron, and he never does, but he will try as hard as anybody. I’ve become friendly with most of these guys.

Whose skin did you get under the most?

LL. It’s not even close. [Laughs] When LL was here, he wanted to come across the desk and strangle me. We really got into it, and it was high-spirited, bordering on not-good-spirited. But he loved it, and once we engaged and went to commercial, he said, “I love this.”

Do you keep in touch with any of the rappers after battling them?

Nelly and I text. Wayne and I keep in touch. Wale loves/hates me, but we keep in touch via Twitter. It’s a billion to one to connect—you’d bet against it—but it’s here. —Mark Lelinwalla (@xxl_mark)

Watch some of Skip Bayless’ best rapper debates below:

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    Skip Vs. Lil Wayne
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    Skip Vs. Fabolous
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    Skip Vs. Bow Wow
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    Skip Vs. Wale
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    Skip Vs. Joe Budden
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  • CaponeMOB

    FUCK skip bayless. he’s the wendy willliams of the sports world. talks alotta shit. if D ROSE has a bad game,right away he says Rose is overrated. never mind all those clutch shots he makes to win the games. everybody fucks up once in a while.

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    Cracking read!

  • Toppchopp

    Bayless knows best!! Doesn’t go with the flo. Knows whats real. Talks about whats real. You fakers!!

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    I do not disagree with this writing…