Much like Gadsby's standup show, their exchange was better experienced than described.
It was actually not their first time coming face-to-face.
Lewinsky told the crowd that she had gone to see Gadsby's show over the summer and reacted viscerally.
"I have never gone to a standup comedy show and bawled my eyes out as much as I did," she told Gadsby. "And given my history, that was pretty surprising."
In "Nanette," Gadsby criticizes comedians who made Lewinsky their target instead of former President Bill Clinton, "the man who abused his power," Gadsby says in the special.
"I really want to thank you for that," Lewinsky said. "On social media, actually, I've noticed, even if people don't reference 'Nanette', there have been many more people who have referenced their regret at having seen me at just a punchline. I think that comes from what you put into the world."
Lewinsky's voice wavered as she thanked Gadsby.
"When we have an easy punchline, I think we have to acknowledge that we're dehumanizing actual human beings," said Gadsby, who added that meeting Lewinsky was "an amazing moment" because she felt her message had gotten through.
"It was a genuine attempt to extend an apology from an art form that profited off shaming you," Gadsby said. "And there's so many people like that."
Gadsby pointed to the late Amy Winehouse as another example.
"[She] was a person we found so easy to laugh at in the midst of witnessing something quite devastating, and we keep doing this and we have to work out ways [to change it]."
Netflix does not release ratings data, but Gadsby's special has spurred many conversations since its June debut on the streaming service, from debates about comedy content to whether the at-times emotionally heavy show counts as comedy at all.
Though she had been a popular figure in other markets before her special, its release catapulted Gadsby into a new realm of awareness in American pop culture.
Gadsby admitted she finds the increased attention "very foreign."
"I find (it) uncomfortable," she said.
She sees some limits on her newfound popularity in the states, however.
When asked whether she would ever host "Saturday Night Live," Gadsby said, "It's not a real question because I won't be asked."
Why, Lewinsky asked.
"I'm not a friend of them. They're not fans of my work," she said. "It's fine. We'll cope."
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