Since then, Gillis has risen through the comedy ranks: Matt and Shane's Secret Podcast, where Gillis has made some of his controversial comments, has over 80,000 paid listeners on Patreon. He launched a web series with John McIver, released two comedy specials, toured the country and most recently In partnership with Bud Light.
In his monologue, Gillis implored the audience to leave his jokes in the past, saying: “Please don't Google that. It's okay. Don't even worry about it.”
But its new parts weren't quite PC.
After recognizing his parents in the audience, he said his mother once asked him when they stopped being best friends. As an answer, he asked the audience: Do you remember when you were gay? Do you remember when you were just a young gay boy?
Gillis explained that every boy is his mother's “gay best friend” until he masturbates for the first time, and then “she says, 'When is this guy leaving the house?'
He also began creating stand-up content that became a hit for him online: “I don't know if you can tell by looking at me, but I have family members with Down Syndrome.”
Seemingly sensing the audience's discomfort, he paused to remark: “Look, I don't have any material that can be shown on television.”
Next, he imagined a future scenario for his niece with Down Syndrome and her three adopted black siblings. At one point, he said, a white kid would taunt her with an old word for someone with mental disabilities — a term Gillis says on stage — “and then three black kids would come out of nowhere and start wailing over that cookie.”
Gillis also took the lead in several skits during the show, including a trailer for the fictional film “White Men Can Trump,” in which he pitted an impersonation of Donald Trump against James Austin Johnson's popular caricature. After lacing up some gold Trump sneakers (Which retails for $399), Geillis turns into an orange braggart who can convince people not to believe what they see. (When he shoots a volley in basketball, he says to his teammates: “I didn’t miss, the ball went in.”)
Gillis, sporting a deep tan, signature Trump hair and an extra-long red tie, is greeted by Johnson (who portrays the real Trump), who tells him: “The real magic has been inside you all along.”
“Wrong,” Gillis replies. It comes from the shoes, and you look so stupid and frankly so rude walking in here like that.
“Wannabe web expert. Twitter fanatic. Writer. Passionate coffee enthusiast. Freelance reader.”
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