Kenan Thompson Looks Both Ways

Consider just a few of the things that have happened since Kenan Thompson joined Saturday Night Live in 2003: the U.S. elected four presidents (including the first Black president), almost everyone in the country got a smartphone, and massive cultural shifts like same-sex marriage, #MeToo and Black Lives Matter have rocked our world.

Lots of milestones, for sure. Meanwhile, Thompson himself has been marking a milestone, having just wrapped his twentieth season on the venerable sketch showcase. He is the longest-serving cast member in the history of television's longest-running network variety show.

How has he done it? Well, just recall some of his side-splitting impersonations — Steve Harvey, Al Sharpton, Charles Barkley, for starters — and enduring sketches like "Black Jeopardy!" and "Come Back, Barack." With that versatility and splendid silliness, he has endeared himself to his SNL colleagues and to a loyal audience that now awaits season forty-nine.

Yet for this nose-to-the-grindstone Taurus, his anniversary year hasn't prompted much gaiety or waxing philosophical. It's not so much that the decades since his SNL debut have been a blur — it's that the stage in Studio 8H in New York City's 30 Rock has been one of few constants as the world around him whizzed by.

"It's hard to gauge what that time really feels like," Thompson reflects via Zoom. He's in his office, getting ready to pick up his two daughters — Georgia, eight, and Gianna, four — from school, as he does nearly every day.

"You only pay attention to that night or the next day. "All my memories are in that same building, same studio, same dressing room. Once I start looking back, I'll start seeing that I've done a pile of work. And when I start listing the people I've worked with, it's like, 'Okay, yeah. I've been there for a while.'"

A while, indeed. His work product stands like a veritable pyramid amid ever-shifting sands: he's appeared in more than 400 episodes and 1,500 sketches. In some of those, Thompson played alongside cultural heroes who've since passed away. A hysterical "Scared Straight" bit with Betty White led to her Emmy win in 2010 as Outstanding Guest Actress (she played his felonious grandma Loretta), and in a 2018 installment of "Black Jeopardy!," Thompson as game-show host Darnell Hayes parried with Chadwick Boseman as T'Challa of Black Panther.

The spirits of dearly departed colleagues, like writer and cast member Norm Macdonald, linger in SNL's hallowed halls, too. "We keep their pictures up," Thompson says. "So that alone is a daily emotional kind of thing, missing the talented people that you spent so much time with in the trenches."

Naturally, working through all those epic epochs meant also bearing witness to some painfully unfunny periods — 2020 being the most obvious example. There wasn't a whole lot to laugh at during the Covid pandemic, especially during its early days in New York City. But for Thompson, making people laugh isn't just work — it's a higher calling, one that was instilled during his growing-up years in Atlanta, where he and his brother and sister attended the non-denominational Hillside International Truth Center.

"Growing up religious," he says, "we learned that your life has purpose. Mine was shown early: putting smiles on people's faces. I call it my purpose because it feeds me."

Thompson began feeding his fever as a child actor, appearing in local productions like The Wiz and soon in front of the camera on CNN's Real News for Kids. His brother, Kerwin Thompson, recalls being blown away by Kenan's talent when his little bro was five or six.

"One day our parents told us we couldn't have company," says Kerwin, a veteran actor currently seen as King Silas in the Disney+ series The Quest. "I pass Kenan's room, and I hear all these people. I peek in and see he's by himself with Star Wars figures, doing all the voices. That was the start of us doing impressions, performing for company."

Nickelodeon launched the teenage Thompson into stardom. He was so adored on the sketch show All That — where he portrayed characters like the goofy, pseudo French–speaking Pierre Escargot — that he was quickly leading spinoffs: Kenan & Kel, which cast him and Kel Mitchell as mischievous high school kids, and the 1997 film Good Burger, based on an All That sketch.

Good Burger is something of a cult classic — so revered that Thompson and Mitchell have teamed up for a sequel, Good Burger 2, to satiate fans who've begged for a follow-up since the original. It's expected to drop on Paramount+ later this year.

Mitchell says he considers Thompson family, their bond forged by growing up together on TV. "We have a brotherhood," Mitchell says. "That's awesome to me, because you don't get that all the time in this business. When [someone] says 'Cut!' you might not see that actor again. He's just a good dude. He's a team player, and he really understands the business."

Despite his experience, Thompson bombed his first SNL audition. A do-over earned him a slot in season twenty-nine, but his first days weren't much smoother. "I was just wandering around, not knowing what to do," he says. "Writing was foreign to me. I wasn't responsible for writing at Nickelodeon. I was like, 'Shit, did I forget to learn something?'"

Fellow cast member Maya Rudolph threw him a lifeline: an idea for a sketch based on an exchange between Wanda Sykes and Bill Cosby at the 2003 Emmys. Thompson nailed his Cosby impersonation and heightened the ridiculousness of the bit, which ended with him punching Rudolph, as Sykes, in the face. "If it wasn't for that sketch, I don't think I would have been in the show," he admits. "There's a lot of moments like that for newbies. But you've got to figure it out. Quickly."

And he did. Thompson has collected six Emmy nominations and one Emmy win: in 2018, he (with Chris Redd, Will Stephen and Eli Brueggemann) won the award for Outstanding Original Music and Lyrics for the song "Come Back, Barack." The previous year, he was nominated in the same category for the song "Last Christmas," from the "Jingle Barack" SNL music video. His other noms are for acting: in 2018, 2020 and 2021 for Supporting Actor in a Comedy Series, for SNL; also in 2021: Outstanding Lead Actor in a Comedy Series for his NBC series Kenan.

By 2022, he was hosting the Emmys. All the while, on SNL , he's been consistently strong in myriad ways: he kills at deadpan, he creates personas that fill the screen (Diondre Cole of the recurring sketch "What Up with That?" being the gold standard) and he happily fades into the background to let someone else shine.

"No matter the scene, you can tell he's having fun," says SNL senior writer Bryan Tucker, who's worked with Thompson for eighteen years. "That warmth shines through and lets the audience relax and enjoy whatever character he's playing.

"We still struggle sometimes," Tucker says of the continual effort to get sketches on the show. "But we both know it's a long game, and there are other episodes to come. That's part of what Kenan has taught me — look at your career from a distance, and don't worry too much about the day-to-day. Kenan understands that you can work hard without the panic."

Thompson is now such an SNL institution, he's earned the privilege of deviating from format, at times using the live show to share messages from his heart. Case in point: the cold open of January 28. Playing off the discovery of classified documents in the homes and offices of the former POTUS and veeps, the bit had Mikey Day playing Attorney General Merrick Garland and Thompson as an FBI agent. It was boilerplate SNL fare — until Thompson went rogue.

Days before, Memphis resident Tyre Nichols had died after being beaten by police, and protests were swelling to national attention. As the otherwise benign skit concluded, Thompson cut in with a devastating line: "Hey boss ... we gonna head down to Memphis and make sure justice is served there too, right?"

It was a subtly militant statement, not because of its content, but the subtext: I'm aware of what's happening to Black people in America, and I won't be quiet about it. "Everybody knew what I was talking about, without having to say it," he says. "It felt good to call that out." The moment said a lot about Thompson's seniority — and his knack for deft maneuvering around identity politics.

After all, who else has the range to host the Nickelodeon Kids' Choice Awards and the National Hockey League Awards and appear on the syndicated hip-hop radio show The Breakfast Club — without raising an eyebrow in any disparate demo? He's able to do so, in part, because he's kept his comedy clean. "I always wanted my mom or my grandma to be able to watch me," he explains.

But it goes further than that. Everybody loves Kenan. And it's always been that way.

"He's always been easygoing and kind," brother Kerwin says. "He's a very quiet person; he leads by example. I've learned how to be gracious through him."

Said grace has helped him skirt controversy — though one incident still stings. In 2013, after a decade of making audiences howl with impersonations of Whoopi Goldberg, Maya Angelou and Oprah Winfrey, Thompson declared he'd no longer play women. Playing women started to feel expected and old, he said, but he was also echoing what people were saying online: Why doesn't SNL have any Black women who could play Black women?

Then, in a subsequent interview in TV Guide , he was quoted as saying, "They never find ones that are ready." What he was trying to say, he would later explain, was that the standard places for discovering talent — Second City, the Groundlings, et cetera — were not teeming with people of color. But some interpreted his comments to mean Black women aren't funny enough for SNL, which triggered swift scorn on social media.

"It was shitty," he recalls. "[People] were mad. I wasn't saying that Black women can't do the show or aren't funny. That's not my vibe; that's not my energy. The bigger issue was that because they felt that I could handle [playing Black women], they didn't have to think about [finding them]. So it was like, let me close that door so they're forced to go [and look]."

As more Black women began to audition for the show, he made a point to show up and clarify his statement to put them at ease. Leslie Jones, a cast member and writer on SNL from 2014 to 2019, was one of a few who, in the room, voiced her displeasure at what she believed Thompson had said. Things cooled once he explained himself, and they've since become friends.

Uncomfortable as the drama was, no one can deny its ultimate effectiveness: SNL has become increasingly inclusive, with cast members like Ego Nwodim and Punkie Johnson in front of the camera and more people of color writing. He's not entirely responsible for that, of course: more inclusion initiatives exist today, and more people of color see TV writing as an option. Yet as SNL's elder statesman, Thompson has more influence than most. His relationship with creator–executive producer Lorne Michaels helps.

"He's always been like a father figure to me," says Thompson, whose star on the Hollywood Walk of Fame, bestowed in 2022, was placed next to Michaels's. "He's one of my greatest mentors. He's taught me a whole lot about comedy, show business — what a show should look like, television fundamentals."

He's put his education to good use, taking on new challenges. He cofounded a production company, Artists For Artists, with John Ryan Jr. in 2021, the same year he earned his Emmy nom for Kenan. That nomination was for acting, but Thompson was an executive producer of the series (which ran for two seasons) in addition to its star.

"I'm very intrigued by the business side of things these days — making deals in a bunch of different areas," he says. "I always have been, but now I get to be an actual participant, which is exciting."

At press time, there was no word as to whether he'll return to SNL for a twenty-first season. He's been rumored to be leaving for years, but given the vast opportunities for SNL alums, the more intriguing question is, Why has he stayed this long?

"Mostly it's because it's nice to be asked back," he says. "But stability factors into it. It's not like SNL was my first big moment. I know what I'm quote-unquote missing, and I ain't really missing much."

One of the perks he's getting is a reliable schedule that allows him to walk his daughters home from school. And when he's stopped by fans on the sidewalk, it's usually by middle school-aged boys rather than seen-it-all Manhattanites.

"It's flattering," he says. "And it gives me an opportunity to drop that seed of, 'Y'all behave yourselves, and have a good day at school.' It's my opportunity to make an impact. You never know people's situation at home or whatever. It's just letting the kids know, 'All of us adults are looking out for you.'"

The past twenty years may have flown by for Thompson, but those walks with his girls give him time to slow down and, jokes aside, continue to practice living a purpose-filled life. "It's a service kind of existence," he confirms. "My mindset is to encourage or uplift or help. So yeah, I'm a giver, for sure."

His millions of fans already knew that, of course. And having happily taken all that he has to give these past two decades, they'll happily take two more.

The interview for this story was completed before the start of the WGA strike on May 2.

This article originally appeared in emmy magazine issue #6, 2023, under the title, "Look Both Ways."