Since then, Gillis has risen through the ranks in the comedy world. “Matt and Shane’s Secret Podcast,” where Gillis made her controversial comments, has more than 80,000 paying listeners on Patreon. He launched a web series with John McKeever, released two comedy features, toured across the country, and recently partnered with Bud Light.
In her monologue, Gillis implored the audience to leave her jokes in the past, saying: it’s okay. Don’t worry about that either.
But his new bit wasn’t exactly PC.
After recognizing his parents in the audience, he said his mother once asked him when they stopped being his best friend. In response, he asked the audience: “Remember when you were gay? Remember when you were still gay?”
Gillis explained that every boy is his mother’s “gay best friend” until he masturbates for the first time, and then “it’s like, ‘When is he leaving the house?'”
He has also embarked on stand-up content which has been very effective for him on the internet. “I don’t know if you can tell by looking at me, but I have a family member with Down syndrome.”
As if sensing the viewer’s anxiety, he paused and said, “Look, we don’t have anything to show on TV.”
After that icebreaker, he imagined future scenarios for his niece with Down syndrome and her three adopted black siblings. At one point, when a white kid teases her with an outdated term for mentally ill people (something Gillis says on stage), “Then three black kids come flying out of nowhere and crackers. “I start crying as it rings,” he said.
Gillis also starred in several skits during the show. That included a trailer for the fictional film “White Men Can Trump,” which features a Donald Trump impersonation set against James Austin Johnson’s acclaimed caricature. When he dons a pair of gold Trump sneakers (sold for $399), Gillis transforms into an orange-hued thug who convinces people not to believe what he sees. (When he shot an air ball in a basketball, he told his teammates, “I didn’t miss. It went in.”)
Johnson (playing the real Trump) greets Gillis, who is spray tanned, sporting President Trump’s signature bangs and wearing an extra-long red tie, telling him, “The real magic is always inside you.” “It happened to me,” he says.
Gillis replies: It’s because of the shoes and coming here like this makes you seem like a very stupid and frankly very rude person. ”
