Last year, Matt Friend, just four years out of college, stood with microphone in hand surrounded by some of the world’s most powerful people and said: “It is really a tremendous opportunity to be at the most failed dinner anybody has ever seen. Great to see you losers.”
Then he cast his eye toward the stage and, continuing as then-Republican presidential nominee Donald Trump, said: “It’s quieter than ‘Sleepy Joe.’ Hello, Joe. Great to see you.”
President Joe Biden waved back, smiling politely.
Friend, an impressionist/comedian who grew up on Chicago’s North Side, segued seamlessly from Trump to U.S. Sens. Bernie Sanders and Mitch McConnell, before closing out his appearance at the 2024 White House Correspondents’ Dinner with former President Barack Obama.
It was a moment he’d been preparing for for two decades, beginning when he was 4 years old — mimicking the characters from “Austin Powers: International Man of Mystery.” At Lincoln Park’s Francis W. Parker School, Friend once stood up during an assembly and did a spot-on impression of the school’s principal, Daniel Frank.
On Saturday, Friend will be three blocks from the school as the night’s headliner at the Park West.
“Something for everybody — old references, newer references. Everything from Milton Berle to Timothée Chalamet,” Friend said during a chat last week.
Friend, 26, does so many quick-fire impressions (250+, according to his website) that it feels as if his brain is an audio library from which he can simply pluck Trump, Obama, Elon Musk, Jennifer Coolidge and hundreds more with a twitch of his head. He started out absorbing comedy on YouTube: “Family Guy,” “The Simpsons,” “Saturday Night Live.”
In high school, he interned at The Second City.
“So Chicago comedy … had a a big impact,” he said. His mother owns Chicago-based Big.Fat.Cookies and his father works in finance. “They’ve always been enormously supportive,” he said.
Theresa Collins was Friend’s advisor at Francis Parker. He would come into her office, they’d chat and then he might break out an impression of country music star Josh Turner.
“I have this distinct memory of him coming in … and then all of a sudden, he’d (sing), ‘Baby, lock the door and turn the lights down low …,’ ” Collins said.
She was there too for the principal impersonation, which she described as “epic.”
Friend gained fame from his walks about New York City, where he would encounter celebrities — comedians John Oliver and Sebastian Maniscalco and talk show host Andy Cohen, among many others — and take videos of himself impersonating them. He would then upload the hilarious results onto TikTok and Instagram.
No celebrities — not one, he said — ever told him to get lost.
“I’m not ambushing people …,” he said. “It’s out of respect and admiration, and then it kind of organically happens.”
Earlier this year, he appeared on the red carpet at the Golden Globes, chatting with and impersonating Jeff Goldblum, Paul Giamatti, Nicolas Cage and others.
Friend said he can’t quite explain how he does what he does.
“I’ll walk down the street and King Charles comes out,” he said. “I don’t really think about it. It’s just sort of part of my life.”
He is clearly, though, a student of history and a keen observer.
He’s perhaps best known for his political impersonations, including a Trump that has the perfect Trumpian growl, the hissing intake of breath, the hallmark hand gestures. His return to office is “a boost to political comedy, regardless of who you voted for,” Friend said. “It’s not just Trump, it’s the people around him: (U.S. Secretary of Defense Pete) Hegseth, (Vice President JD) Vance. It’s like a clown car.”
He has fans in the actors Jamie Foxx and Austin Butler and, apparently, in Obama.
Friend said he met a representative from the Obama team while the comic was in D.C. for the correspondents’ dinner. A few months later, Obama’s team reached out — to meet in Chicago before the Democratic National Convention.
“I’m, like, freaking out,” Friend recalled. “Suddenly, I find myself in a room (with Obama), and I’m doing all the greatest hits. … It was an insane, insane moment.”
These are “insane,” even perilous, times for entertainers, facing attacks, some would argue, from both the left and the right — from so-called “cancel culture” to Trump’s threats to cut arts funding.
What’s a comic to do?
“I don’t fear that. … I just always do what I think is right,” Friend said. “If you’re living your life like that — fearful of one side or the other — you’re not going to go far.”