As the the Toronto singer was about to be introduced, Mayer explained that the comedian had just met Caesar and heard him sing for the first time — to which Chappelle said, "Yeah, very gay."
After some off-camera snickers, Chappelle tried to recover by saying, "Daniel Caesar is a musician from Toronto that I just met tonight — black. I got jealous, I didn't know John had other black friends."
When Chappelle and Mayer asked Caesar if he was ready to set up and perform, the singer retorted, "What the fuck was that?"
Then, when asked by Chappelle if he was offended, Caesar said, "Yeah."
Both parties admitted to being drunk, and then Mayer stepped in and tried to "clean it up." As Mayer attempted to draw an apology out of Chappelle, Caesar conceded he was being "sensitive."
"I'm trying to think about this," Caesar said off camera. "Maybe I am being sensitive."
Chappelle countered, "Daniel, I thought about it. You are."
As Mayer continued to run damage control, his two guests seemed to patch things up and Caesar got in front of the camera and threw his arm around Chappelle and proclaimed his fandom for the comedian.
Watch the whole strange ordeal (and a teaser recap of Caesar's performance) below.
It's not the first time Chappelle has "accidentally" made homophobic "jokes." His 2017 Netflix specials came under fire by many for their anti-LGBTQ rhetoric and language.
The brilliant (and recent Grammy winner) @danielcaesar stopped by Current Mood last night to play his song "Get You." Here's a sneak peak at the HD video to be posted later this week to IGTV. We're in a golden era of new music thanks to musicians like Daniel. Definitely worth a follow. ✨🎸✨