Shane Gillis' Most Controversial Trump Impressions

Shane Gillis broke into the mainstream comedy scene amid controversy. He was hired as a cast member on "Saturday Night Live" in September 2019, and then unceremoniously fired days later when clips surfaced of Gillis using racial slurs while making insensitive jokes on his podcast. 

Later that month, Gillis did his first stand-up set since being canned from "SNL" and performed a chunk of material about then-president Donald Trump. "I don't want you to think I'm too pro-Trump," Gillis joked to the crowd at The Stand comedy club in New York, per USA Today. But instead of pumping the breaks after his "SNL" dismissal, the comic delivered more controversial material. "I will say this: Of all the presidents I've been alive for, Trump would definitely be the funniest one to see get shot," Gillis told the crowd.

Trump became a common topic for Gillis on and off-stage. The comedian was excited when he met Trump at a UFC event. "His vibe was just complimenting every single person that came up to him," Gillis recalled on "Matt and Shane's Secret Podcast" in the summer of 2023. "He'd just say, 'You're doing great. Wow you look great,'" Gillis added.

Perhaps seeing Trump in person helped mimic the former POTUS, as the comedian has honed his Trump impression since his infamous firing. Over four years after being let go, Gillis was invited back on "SNL," but this time as a host. Naturally, he broke out his Trump impersonation for the show. 

Shane Gillis bashes Donald Trump's gold sneakers

When Shane Gillis hosted "Saturday Night Live" on February 24, multiple fans of the comedian were disappointed with the opening of the show. "I waited that entire cold open for SNL to do the one thing everyone wanted them to do, have Shane Gillis do a Trump impression," one viewer wrote on X, formerly Twitter, at the time.

It turned out that the comic had saved his Donald Trump impression for a pre-recorded sketch titled "Trump Sneakers." The sketch was a send up of Trump's ostentatious $400 gold-colored sneakers, and featured Gillis as a man who was terrible at basketball until he was gifted magical sneakers. Those gold Trump-brand sneakers helped transform Gillis' character into the former president. "I didn't miss. It went in," the faux-Trump said after missing a shot on the basketball court. The premise is that although the sneakers did not give him basketball abilities, it allowed Gillis' character to bully people in a Trump-like manner.

One scene showed faux-Trump in bed with the sneakers on alongside a woman. "That was the most fantastic love-making you've ever had," Gillis' Trump said while trying to convince the unsatisfied partner. Later, Gilllis' Trump steps on a scale, and shouts at it until the number drops down from 253 pounds to 170 pounds. Of course, that Trump impression was mild compared to the one that landed Gillis in hot water with the government.

Why the Secret Service investigated Shane Gillis

During his 2021 comedy special "Live In Austin," Shane Gillis expanded his premise about Donald Trump being hypothetically shot while he was Commander in Chief. Gillis joked about the assassination attempt taking place while Trump was in a debate. "My opponent's gay," the comedian said in his Trump voice. "The shooter would be coming at him, he'd be like, 'Sit down,'" Gillis said. "He'd definitely make a funny noise ... He'd fall funny."

That joke was shared by viewers and media outlets, which drew the attention of the Secret Service. According to a report from The Messenger, the Secret Service released an email titled "Discovery of Threatening Statement by Comedian Shane Gillis" (via Cracked). Reportedly, the Secret Service performed a thorough background check on Gillis to ensure he was not an actual threat to Trump. "The Secret Service is aware of the comments made by Mr. Gillis ... We can say, however, that the Secret Service investigates all threats related to our protectees," Secret Service Deputy Special Agent in Charge Rosanna Donaghey told The Messenger. The agency found no evidence of foul play and decided not to press charges against the comedian.

The Secret Service may not have been fans of that comedy bit, but Dave Chappelle was. While performing in May 2023, Chappelle brought Gillis on stage and asked him to perform the Trump getting shot routine. Later that year, Gillis did another Trump impression on his new comedy special.

Shane Gillis says Joe Biden is impervious to Donald Trump

Shane Gillis titled his 2023 Netflix comedy special "Beautiful Dogs" after a quote from Donald Trump. One of the more popular bits on that special involved the comedian doing an impression of Trump debating Joe Biden. Gillis took shots at both Trump and Biden during the special. "Biden is Trump's kryptonite in a debate," Gillis told the audience while explaining that Biden was too slow to realize he was being insulted by the former president. "He tries it. 'You're a loser. Your son did crack.' And Biden's just, 'What?!'" Gillis joked.

Then Gillis segued into how unhinged Trump acted while delivering a press conference to announce that ISIS leader Abu Bakr al-Baghdadi had been killed. "Abu Bakr al-Baghdadi is dead. He died like a dog," Gillis said in his Trump voice. Gillis laughed at the notion of Trump delivering an "unprepared speech." Despite the edgy material, fans applauded Gillis's impersonation. "If nothing else, we need trump to win again so Shane has more content to mimic. That press conference impression was spot on," one YouTube user commented.

Gillis fans enjoyed seeing him use the impression for his stand up, but one of the fan favorites was from a sketch that really pushed the boundaries.

Donald Trump in the dating world

Years before Shane Gillis used his Donald Trump impression for a sketch on "Saturday Night Live," he used the persona on his own sketch show "Gilly and Keeves" in 2021. The sketch titled "Trump Speed Dating" envisioned how it would look for the former president to try his hand at a speed dating session. "I was asked to speak at this hotel, turns out there's some kinda p**** banquet going on," Gillis said as Trump.

The women sitting across from faux-Trump are mostly revolted by him, and the would-be dater takes his photo while telling him off. "Social media. They had to take it away. I was too good," Gillis says as Trump. As the females unload their grievances on Gillis' Trump, a war of words ensues. "I'm disgusting? I saw you walk in and I said, 'Is this a pig? I didn't know they were letting pigs in,'" Gillis's Trump says. At the end of the sketch, the fake-Trump is matched with a Trump supporter who is rough around the edges. She sports a T-shirt that has the American flag, but in place of stripes there are automatic weapons. Eventually, Gillis' Trump hits it off with this hopeful dater.

A year after that sketch was released, Gillis was able to rub elbows with the elite and even visited Mar-a-Lago.

Shane Gillis describes the residents of Mar-a-Lago

Shane Gillis became a fixture on Joe Rogan's "The Joe Rogan Experience" podcast, and the host frequently asks the comedian to use his Donald Trump impersonation, which on more than one occasion pushed the envelope on decency. On an episode of "JRE" from September 2022, Rogan asked Gillis (as Trump) if he had plans to run in the 2024 presidential election. "The crooked FBI, they went into my house. They haven't found anything," Gillis responded in his best Trump voice.

Then the stand up comic recalled visiting Trump's residence. "I saw the king, I went to Mar-a-Lago. I was in Mar-a-Lago it was me and like 10 people," Gillis told Rogan and other podcast guests. In April 2022, Gillis uploaded a photo to Instagram of himself posing outside a palatial home at the famed Palm Beach resort while putting two thumbs up with a giant smile on his face. The "Beautiful Dogs" comedian said that Mar-a-Lago was picturesque, but he did not fit in with the residents. "Dude, the only people there are 70-year-old billionaires, and they're all wearing MAGA hats," Gillis added about Trump's residence.