Chris Matthews Asks Michael Che Who the ‘Funniest Black Guy’ Is in Cringeworthy Live Interview

No he didn’t! MSNBC’s Chris Matthews asked Saturday Night Live star Michael Che who the “funniest black guy” is in a superuncomfortable interview on live TV.

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The comedian, 33, and his SNL Weekend Update cohost, Colin Jost, sat down with Matthews to talk politics at the Republican National Convention in Cleveland, Ohio, on Wednesday, July 20. Their conversation began with some uneasy banter about racism and comedy. When their discussion quickly fell flat, Matthews decided to cover up a moment of silence with an incredibly awkward question.

“What do you think, funniest guy — funniest black guy?” the 70-year-old broadcaster asked Che, who is black.

Che and Jost, 34, appeared to be taken aback by Matthews’ off-putting query. “You know what, I’m going to say [Bill] Cosby so nobody gets mad at you,” Che replied. “Now that’ll be the headline.”

Chris Matthews, Michael Che and Colin Jost
Chris Matthews, Michael Che and Colin Jost

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Matthews offered an inexplicable response to Che’s answer by saying, “Say nothing bad about the dead, you know you’re not supposed to do that.”

Confused, Che blurted out, “Wait, what?!” while Jost pressed Matthews: “Did [Cosby] die [while we are] on air? Do we not know?”

Not quite sure where to go from there, Matthews decided to change the topic to former presidential candidate Ben Carson’s remarks comparing presumptive Democratic nominee Hillary Clinton to Lucifer. The men also spoke about the appeal of Republican presidential nominee Donald Trump before Matthews made things weird again by asking Che and Jost what hotel they were staying at.

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“What hotel?! I’m in room 215 at the Beachwoods-something.… What do you want me to — what are you doing?!” Jost asked Matthews with a laugh. “I don’t know if you’re trying to get us laid or killed!”

“Both is possible,” Matthews reasoned.

Watch the cringeworthy clip above.

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