MSNBC host Chris Matthews asked African-American Saturday Night Live comedian Michael Che who the "funniest black guy" is during their coverage of the Republican National Convention.
"You are so funny," Matthews said. "What do you think? Funniest guy? Funniest black guy?"
"Funniest black guy?" Che repeated incredulously.
Fellow "Weekend Update" host Colin Jost burst out laughing at Matthews' question.
"I’m going to say Cosby so nobody gets mad at you," Che said, referring to Bill Cosby, who has been accused by dozens of women of sexual abuse.
The three bantered about the GOP and the state of politics in America, but Matthews couldn't help but close the segment by returning to his awkward earlier query.
"Thank you guys for coming on today," Matthews said. "You lit up the charts."
"I had a great time, this was great," Che said.
"So it's Chris Rock, right? Funniest—" Matthews said, putting his hand on an uncomfortable-looking Che's shoulder.
"Yeah!" Che said.
"Michael Che just says Chris Rock is the best in the business, not just in a particular community," Matthews said.
Matthews has come under fire before for comments that could best be described as racially insensitive, such as referring to Sens. Ted Cruz (R., Texas) and Marco Rubio (R., Fla.) as "two Cuban guys."