Since then, Gillis has risen through the comedy ranks: “Matt and Shane’s Secret Podcast,” where Gillis made some of his controversial comments, has over 80,000 paid listeners on Patreon. He launched a web series with John McKeever, released two comedy specials, toured the country and recently partnered 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 fine. Don’t even worry about it.”
But his new bits weren’t exactly PC.
After recognizing his parents in the audience, he said his mom once asked him when they stopped being best friends. As an answer, he asked the audience: “Remember when you were gay? Remember when you were just a gay little boy?”
Gillis explained that every boy is his mom’s “gay best friend” until he masturbates for the first time, then “you’re like ‘When’s that b—– going to leave the house?’”
He also launched into stand-up content that does very well for him on the internet: “I don’t know if you can tell by looking at me, but I do have family members with Down syndrome.”
Seeming to sense the audience’s unease, he paused to note that “Look, I don’t have any material that can be on TV.”
After that ice breaker, he imagined a future scenario for his niece with Down syndrome and her three adopted Black siblings. At some point, he said, a White kid will taunt her with an outdated word for a person with mental disabilities — a term Gillis says onstage — “and then three Black kids come flying out of nowhere and start wailing on that cracker.”
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 put his Donald Trump impersonation up against James Austin Johnson’s lauded caricature. After lacing up some gold Trump sneakers (which sell for $399), Gillis is transformed into an orange-tinted blowhard who can convince people not to believe what they see. (When he shoots an air ball in basketball, he tells his teammates, “I didn’t miss. It went in.”)
Gillis, in a deep spray tan, the signature Trump hair swoop and a very long red tie, is greeted by Johnson (portraying the actual Trump), who tells him, “The real magic has been inside of you all along.”
Gillis replies, “Wrong. It comes from the shoes, and you’re coming off as very stupid and frankly quite rude walking in here like this.”
