
You’ve probably seen Matt Friend on your Instagram feed impersonating a famous person: Donald Trump, Jennifer Coolidge, Rami Malek, King Charles, Andy Cohen, Howard Stern, Stanley Tucci, Jeff Goldblum, Joe Biden, you name it. Really, they’re uncanny. Close your eyes and you’ll swear you’re hearing the real Bill Gates talk about his relationship with Jeffrey Epstein.
Of course, social-media platforms are awash in funny people doing impersonations of famous people. But Friend, 28, has emerged as one of the most popular from this crowded class, with more than 2 million Instagram followers and nearly as many on TikTok. You can chalk it up to pure talent; he’s better than most. But he’s also an equal-opportunity satirist, punching at DJT and Joe Biden with the same ferocity, expanding his appeal exponentially. A couple years ago, he performed at the White House Correspondents’ Dinner—earning a chilly reception from the D. C. elites and headlines for an off-color joke. (“I am killing this dinner harder than Kristi Noem kills the puppies.”) Still, the event was a milestone, proof that Friend had made the difficult leap from online to IRL entertainer. He has since appeared with a mic in hand at the US Open, Milan Fashion Week, the NHL Awards, and the Oscars. Earlier this year, he hosted America Laughs with Matt Friend for CNN. He’s on tour honing material for his first stand-up special in 2027. Pretending to be other people has worked out very well for Friend.

Lead image: Jacket, shirt, and sweater by Boggi Milano; Overseas Tourbillon watch by Vacheron Constantin. Above: Vintage Barbour jacket, stylist’s own; jacket by Cesare Attolini; shirt by Paul Smith; tie by Sid Mashburn; trousers by Jacob Cohën; shoes by Santoni; socks by London Sock Company; glasses by Ray-Ban Meta.
But when it comes to style, he’s his own man. Unlike most of his fellow comedians, Friend dresses up onstage, opting for sharply tailored suits from brands like Brioni and Zegna instead of tees and hoodies. “I was drawn to this period of show business that has disappeared,” he says. “It’s a different world now; people can make content from their house. But I want to bring glamour back.”
He credits old-school comics like Johnny Carson, Don Rickles, and Rich Little with informing his style—both sartorial and comedic. But his choice of attire is also rooted in the kind of work he does. Celebrity impressions demand a careful balance. Play too hard into the character and you run the risk of losing yourself. “I just did the Mark Twain Prize, but I’m not in costume as Donald Trump,” Friend says. “I’m six-foot-whatever me in a double-breasted suit, coming out of my chair launching into my impression. I’m not using props. That helps retain who I am and become my own thing versus the people I’m becoming.”

Jacket by Kiton; shirt and tie by Sid Mashburn; glasses by Ray-Ban Meta.
A native of Chicago, Friend studied at the legendary Second City as a child. He left for Boston after high school—he was declared “Best Dressed” during his senior year, a period during which he was “wearing J. Crew sweaters all the time”—and logged a year at Tufts before transferring to New York University and immersing himself in the N. Y. C. comedy scene. Then the pandemic hit. Isolated at home like the rest of us, with no comedy clubs to visit, Friend started recording himself doing impressions and uploaded them to TikTok, Snapchat, and Instagram.
By 2023, his efforts on social media were reaching critical mass. People were watching, laughing, liking, and sharing. Among them was actor John Stamos—you know, Uncle Jesse from Full House—who took a shine to the young comedian. Friend credits Stamos with providing guidance and mentorship as his career took off.

Throughout it all, Friend has stayed committed to his suited-up style. After all, his audiences pay good money for him to morph his radio-ready voice to sound like presidents and movie stars. And Friend doesn’t exactly play it clean. When you’re dropping more than a few f-bombs during every performance, looking respectable has a tangible effect.
“There’s something I like about the comedian being better dressed than the audience,” he says. “I should be presentable. I shouldn’t be rolling out of bed in a T-shirt.” There’s a sense of rising to the occasion, clothing-wise. That’s true when he’s hosting on the red carpet too. “Being at these big moments requires a great outfit. You don’t show up to an award show in sweatpants.”

Jacket, turtleneck sweater, and trousers by Hermès; boots by Manolo Blahnik.
There are still new heights for Matt Friend to reach. He’s waiting for a shot at his own starring vehicle, something that’s not just another podcast. Maybe a gig where he sits behind a desk and interviews some of the stars he impersonates? Something that airs after prime time? Friend won’t say for sure, but he has thoughts on the format.
“Everybody wants to reinvent late night, whatever that means,” he says. “I don’t think you need to reinvent. Old-school talent meeting new tools is a winning formula. I’m trying to think what that will look like.”

He knows what it wouldn’t look like: “In a basement with a bong, interviewing a conspiracy theorist, with Cheeto dust on my T-shirt,” he says. “I’m trying to draw from the past, stylistically, and make it modern. I’m not gonna be that clean, but I like the idea of looking really good.”
Mission accomplished.
Photographed by Jason Kibbler
Styling by Nick Sullivan
Grooming by Herve Claude
Esquire Executive Design Director: Martin Hoops
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Esquire Editor-in-chief: Michael Sebastian
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