Since then, Gillis has climbed the comedy charts: “Matt and Shane's Secret Podcast,” where Gillis makes some of his most controversial comments, has more than 80,000 paid listeners. Patreon. He launched a web series with John McKeever, released two comedy specials, and toured the country Partnered with Bud Light.
In his monologue, Gillis implored the audience to leave his jokes in the past, saying, “Please don't Google it. This is good. Don't even worry about it.”
But his new bits aren't exactly PC.
He said his mom once asked him when they stopped being best friends after recognizing his parents in the audience. In response, he asked the audience: “Do you remember being gay? Remember when you were a gay boy?
Gillis explains that each boy is his mother's “best gay friend” until he masturbates for the first time, and then “you're like, 'When are you going to leave the house?'”
He also started stand-up content, which is doing well for him on the Internet: “I don't know if you can tell by looking at me, but I have family members with Down syndrome.”
Appearing to sense the audience's discomfort, he paused to remark, “Look, I don't have any material that can be on TV.”
After that icebreaker, he envisioned a future scenario for his niece with Down syndrome and her three adopted black siblings. At some point, a white kid would taunt her with an outdated word for someone with mental illness — a word Gillis says on stage — “and then three black kids come flying out of nowhere and start setting off those fireworks.”
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 performed his Donald Trump impersonation against an acclaimed caricature of James Austin Johnson. After wearing some gold Trump sneakers (Retails for $399), Gillis is transformed into an orange blowhard who can convince people not to believe what they see. (When he shoots an airball in basketball, he tells his teammates, “I didn't miss. It went in.”)
Gillis, in a deep spray tan, with a signature Trump hair sweep and a very long red tie, is greeted by Johnson (portraying the real Trump), who tells him, “You've got the real magic inside of you.”
To which Gillis replied, “Wrong. It comes from the shoes, you are so stupid and frankly so rude to be acting like this here.
