Emmy-Nominated Billy Eichner Reveals His Most 'Painfully Awkward' 'Billy on the Street' Moment

Billy Eichner says of "extremely accomplished and wonderful" rapper Nas, "I don't think he knew what he was getting into"

Billy Eichner has had plenty of awkward moments on television — but there’s one that tops them all!

The Emmy-nominated Billy on the Street star joined PEOPLE Editor-in-Chief Jess Cagle for his signature Q&A session, The Cagle Exercise, and didn’t miss a beat when asked about his most uncomfortable on-camera moment.

“The most awkward moment I’ve ever had on camera was on Billy on the Street — second season with he rapper Nas, who’s an extremely accomplished and wonderful artist, but I don’t think he knew what he was getting into,” recalls Eichner, 38. “One game we played with Nas which did not air because it was just too painfully awkward was called ‘Nas or Santa Claus.’ It was facts about Nas or facts about Santa Claus and he had to tell me whether it was referring to him or Santa Claus, and he was not feeling that tone of humor.”

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It gets better.

Cagle put Eichner on the spot when he asked which celebrity he would kiss.

“If I had to kiss one celebrity right now, it would be — I like an Alec Baldwin circa 1992,” he says. “I like a young Alec Baldwin, not that there is anything wrong with Alec Baldwin right now — any of the Baldwins. Not Stephen.”

Billy on the Street’s fifth season earned truTV’s first-ever Emmy nomination in the category for outstanding variety sketch series.