Dave Chappelle had an incredibly awkward drunken exchange with Grammy Award-winning singer Daniel Caesar during a March 10 episode of John Mayer’s Instagram Live show, Current Mood.

As Mayer began to set-up a performance by noting that Chappelle had just met and heard Caeser sing for the first time, the legendary comedian blurted out “Yeah, very gay,” before jokingly suggesting that he was jealous after meeting him, as he thought that he was Mayer’s ”only black friend.”

Attempting to simply gloss over the jokes didn’t go smoothly, and Caesar could be heard off-camera asking, “What the fuck was that?”

Not one to backtrack on his comedy, Chappelle appeared to get visibly annoyed as Mayer — who admitted he was the only sober one in the room — began low-key attempting to coax an apology.

After reaffirming that he recognized Caesar’s greatness, and politely reminding him that he’s a comedian, the Toronto crooner offered that perhaps he was being too sensitive. The clip ends with the two smiling.

Giving his version of a Jerry Springer final thought, Mayer noted, “Sometimes the gears in your head move super fast and the wrong things get shot through the gears,” to which Chappelle exclaimed, “Whoopsie muthafuckin’ poopsie.”

Watch the whole exchange above.