Kenan Thompson Is Already an ‘SNL’ Legend, but Now He’s Ready and Overdue for More

Kenan Thompson was working on the Warner Bros. lot one afternoon in the early 2000s when he spotted “Friends” star Matthew Perry zooming out of the studio gates in a BMW convertible.

“The sun was shining, he had his sunglasses on and he looked like he could not have been happier,” Thompson recalls. “It was like 2 o’clock in the afternoon. And he was done for the day. It just looked like the sweetest existence I’ve ever seen. That shit sticks out in my mind. Like, he was fucking beaming.”

Thompson, now 42, was no stranger to TV comedy at that point, having been a part of the late 1990s Nickelodeon ensemble sketch series “All That” and then joining with Kel Mitchell to topline the spinoff “Kenan & Kel.” But as those shows came to an end, the young Thompson’s ambitions only grew larger.

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“Especially for anybody that’s been put into the comedy category, a sitcom is kind of like the Holy Grail,” he says. “It was always one of those achievements as far as like, will this ever happen?”

The answer is yes, it’s finally happening. After several attempts at developing his own half-hour network comedy, the “Saturday Night Live” star is ready for primetime. NBC’s “Kenan” is his first fully starring TV vehicle after years of being the seasoned utility player whom everyone else looked to for support — be it on “SNL” or the multitude of projects that have come out of his “SNL” colleagues.

“There’s nothing he can’t do,” says “SNL” supremo and “Kenan” executive producer Lorne Michaels. “He’s one of the greatest of all time. … Kenan may be a genius.”

“Kenan,” which debuts Feb. 16, stars Thompson as a local TV morning host in Atlanta and the widowed father of two young girls. But don’t consider this his “SNL” exit strategy — far from it. Thompson and Michaels have a long-term plan for the star, and more on that in a moment.

Thompson’s unprecedented 17-season run (so far) on “SNL” has earned him four Emmy nominations. He’s the show’s longest-serving player, surpassing Darrell Hammond (14 seasons). As 2021 began and “SNL” took a deserved monthlong break from production, Thompson and the “Kenan” crew were busy producing the single-camera comedy as swiftly as possible in order to adhere to COVID-19 protocols — shooting with multiple cameras, for example, to move faster from scene to scene and not prolong any interactions. But the fast pace will also help get Thompson and one of his co-stars, fellow “SNL” player Chris Redd, back to New York and “SNL’s” Studio 8H full-time by spring. (They’re doing quick weekend commutes in the meantime, to have some sort of presence on the show.)

“He’s the O.G., the wise man,” Redd says of Thompson. “I’m constantly asking about how stuff used to be in comparison to now, and they’re always the most interesting stories. I remember having a conversation with him and Maya Rudolph, and at some point, you sit back and hear them share stories about how things used to be back then versus now. I just pick his brain and want to learn. And I want to make sure I’m bringing my best to impress this guy. This guy made me laugh for years.”

For a large contingent of “SNL” fans — and even for much of its cast — it does seem like Thompson has always been a part of their lives.

As a 12-year-old in Atlanta, with the support of his parents, Thompson was laser-focused in auditioning for commercials, which led to a role in 1994’s “The Mighty Ducks” sequel, “D2,” and then starting in 1996, “All That.”

“I was like, engage me in what you want me to do,” he says, “and I’ll show you what I can do. Luckily that shield of armor, that confident front that I would put up, led to me getting the opportunities to actually learn how to be good in front of audiences. And I was always a very happy, get-along-with, barbecue-y type of guy.”

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“Kenan” director and executive producer Ken Whittingham remembers directing an episode of “Kenan & Kel” in 1999 and being wowed by Thompson way back then.

“I was very impressed with how professional he and Kel were and how committed they were to comedy,” says Whittingham, who much later became good friends with Thompson. “I learned a lot from him about sketch at an early age, and he was just very gifted and very committed. He’s still that same person that I remember him being young. He was never arrogant; he was always really polite. Nothing negative to say about anybody. He’s from the South; he’s a Southern gentleman.”

Years before hiring Thompson on “SNL,” Michaels took his young children to see “Good Burger,” the movie starring Thompson and Mitchell based on an “All That” sketch. For Michaels’ kids, “Kenan was already a star. And I think you can see, there’s something about people learning how to do that much at an early age. You just get better at it.”

After “Kenan & Kel” ended, Thompson’s career was at a crossroads. He scrounged up guest roles on shows like “Felicity,” but he calls it “the realest period of time that I’ve experienced. In between Nickelodeon and ‘SNL,’ I was just surviving, one of the millions of people out here in Los Angeles that are paying their bills however they can. I was caught in between looking young and wanting to be taken seriously. So I would turn down things that would put me back in the kid category, and then I would not be given the green light on things that would boost me out of it.”

Thompson kept sending tapes to “SNL,” but he’d hear back that he looked too young. The big shot came in 2003, when he auditioned with Finesse Mitchell and J.B. Smoove, among others.

“He had all the skills we needed, right away, but also he found a way to shine almost immediately,” Michaels says. “And then he was essential. He became the person everybody would like to have in their sketch. And the audience feels always that, with him, they’re in good hands.”

Thompson says some of the writers and stars on “SNL” knew of his Nickelodeon background, but to others he was an unknown. In those early years he was the “babyface cast member” willing to play any bit character and try to figure out a way to get a laugh.

Michaels says he and Thompson have developed a shorthand during “SNL” shows: “We just make eye contact. I’ll smile; he’ll smile. Occasionally, he’ll do something so remarkable that I’ll walk over and say, ‘God, that was amazing.’ He knows I’m there for him, and I know he’ll always be there for me in the same way.”

Michaels has frequently referred to Thompson as his good-luck charm, and the two have developed a close relationship.

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“Lorne’s my buddy now, which is crazy for me to say,” Thompson says. “I thoroughly respect what Lorne has done, and the fact that he would take the time to dedicate his attention to hopefully getting laughter or an enjoyable moment by being around me is just crazy.”

Director Ava DuVernay says she’s never met Thompson, but she’s a super fan. “He has been the centerpiece of that show for so many years, and has become central to every sketch that I’ve loved,” she says. “I think in the conversation about the greatest ‘SNL’ performers, he’s often left out because we’re thinking of the folks who have moved on and done their TV shows and done their movies. But the longevity, the consistency, the variety, the stick-to-itiveness of his presence there — I think he’s pretty awesome.”

Redd says he bonded with Thompson immediately after joining “SNL” in 2017, and has learned so much from the star just by watching him in action.

“I grew up watching Kenan, but he felt like family immediately,” Redd says. “I’ve never had a big brother before, but he immediately assumed that role and put me on game. ‘SNL’ can be hard especially when you don’t know how to navigate it quite yet, and he’s such a calming presence, like he’s mastered the thing. … Talk to anybody in that building at ‘SNL,’ and they would have similar things to say about Kenan. He’s just a consistently good dude. With raw talent.”

His tenure at “SNL” secure, in recent years Thompson still had good reason to wonder if his sitcom dreams would come true.

In 2012, the actor partnered with “SNL” writer Bryan Tucker — with whom he collaborated on memorable sketches such as “Black Jeopardy” and “What Up With That?” — to develop a half-hour that went nowhere. The next year, he worked with “The Mindy Project” alums Josh Bycel and Jonathan Fener on a show about a volunteer firefighter. That also wound up in turnaround.

“Actors don’t need any more panic buttons, so whenever it felt like there was any kind of disagreements with what I’m doing, it’s like, oh, shit, is my whole career in jeopardy?” Thompson recalls. “Do they think that my taste is awful? Do they not want to be in business with me?”

Thompson being Thompson, however, he quickly chilled out. “They would always explain like, ‘No, it’s not because of you. It’s only because of this, that and the other, and we’ll figure out.’ So after hearing that twice, I was just kind of like, ‘All right, I don’t know what they really want me to do. But hopefully, we’ll get to a place where we’ll come up with an idea that makes everybody happy.’”

At the same time, as the longest-standing player in “Saturday Night Live” history, Thompson knew the pressure was on to make his next move the right one. “It was starting to get close to me being at ‘SNL’ for like, a long time, in everybody’s opinion,” he says. “Not just fans noticing but myself being like, ‘Is there an end date to it? And if there is, I should prepare a bridge for that day.’ Because that was the thing that Lorne always told me from early on: ‘Don’t leave the show until you got a firm hold on that next branch.’”

That branch came via a meeting with writer Jackie Clarke (“Superstore,” “Happy Endings”). Clarke, who lost her mother as a child, had been kicking around an idea about a family moving on from the death of a parent, and Thompson had been considering a similar concept.

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“What if there was a guy struggling with the love of his life not being in his life anymore, and what that would look like?” Thompson says. “And how do you still make that a sitcom? I thought that would be intriguing to watch.”

NBC gave a big production commitment to what was first called “Saving Larry,” and then “Saving Kenan,” and then “The Kenan Show.” Now it’s just “Kenan.” The original pilot, shot in 2019 and directed by Chris Rock, featured Thompson as the widowed father of two girls and Andy Garcia as Kenan’s father-in-law.

Ultimately, network execs thought the show needed more energy — and more laughs. “We just leaned into the situation of my wife passing away a little too heavy,” Thompson says. “It’s much lighter now, and that way we can embrace the fun. Everybody’s aware of the situation but also trying to hold me up on my two feet with joy, instead of everybody crying together.”

“Happy Endings” creator David Caspe, known for his rapid-fire, joke-filled scripts, was added as an executive producer. Kenan’s job was switched from a nondescript real estate gig to a TV morning show host, which opened the universe to the kind of interactions that viewers love seeing Thompson do.

“I think the first [pilot] was sort of a shakedown cruise,” Michaels says. “We found what was good about it and also what I thought the show needed more of in terms of a comedy ensemble, because it is a comedy show. Yes, it will have emotion. But these [emotions] are coming mostly because you think it’d be funny.”

Don Johnson was brought in to take over as Kenan’s father-in-law, while the cast expanded to include Redd as Kenan’s offbeat brother — a suggestion that Michaels made. (“To me it was always sacred ground to try and cast from ‘SNL’ people, but it was rock star Lorne making those moves. I was like, ‘Hell yeah, like bring him over,’” Thompson says.)

And the cast’s riches grew from there, with Broadway star Taylor Louderman as Kenan’s co-host in the show-within-the-show, Kimrie Lewis (“Single Parents”) as his producer and comedian Fortune Feimster — a last-minute addition — as the weathercaster.

“Thank God, they gave us the time to focus in on it,” Thompson says. “Even though it’s my third time around the development cycle, you really only get one shot at it. Once the show launches, it’s either a hit or miss. And if it’s a miss, that’s kind of a big deal. It’s a lot to be stressed out about, but time and working with super professional people like Jackie and then bringing in David Caspe, now we feel like the team is strong.”

A happily married father of two girls himself, Thompson had plenty of personal experience to dig into as he prepared to play a TV dad. He also did some quiet research into how widowers handle the loss of a spouse — most notably, comedian Patton Oswalt, whose wife Michelle McNamara died in 2016.

“I was watching what Patton went through” from afar, says Thompson, who opted not to grill the comedian about his experience. “I wouldn’t know how to engage anybody on that specific topic, especially someone who I adore. And I am a fan of Patton, so everything in me is dying to ask one question. But when I first saw him and met him, I just gave him a giant hug. Like, ‘I just love you.’ And that was it. I couldn’t fathom even bringing up a subject like that. But it was seeing what he said about it naturally, reading his Instagram and different articles, and watching his stand-up, where he talks about it.”

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On “Kenan,” Thompson stars as the widowed dad of daughters played by Dannah Lane (left) and Dani Lane. Courtesy Casey Durkin/NBC

Thompson is also conscious of making sure he’s offering a proper representation of a young Black father on “Kenan.” It’s not lost on him that his show is airing on NBC, where “The Cosby Show” broke barriers in the 1980s for its depiction of an upper-middle-class African American family. One of Thompson’s early signature impressions was Bill Cosby, and he starred as Fat Albert in the 2004 live-action movie based on Cosby’s animated character.

“In its time, ‘The Cosby Show’ was probably one of the greatest shows that had lived,” Thompson says. “It was a show that brought everybody together, and it was all positive. It’s tough to separate the man from the art. That’s the thing about a lot of subjects lately, unfortunately. But what can you say about that subject that doesn’t wind you in a world of shit? You leave it for the history books. My show won’t have drama attached to it like that.”

Thompson has managed to mostly avoid drama or controversy and keep his head above water despite launching his career at such an early age. “I had a very stable home life, a close-knit family,” he says. “I was never taken advantage of when I was being given these opportunities. And I never wanted to ever front on my immediate family, which led to not wanting to front on other people. That just kept me just eating humble pie, throughout the entire experience.”

If there has been one misstep in his time at “SNL,” it’s a 2013 TVGuide.com interview in which Thompson now says he was misunderstood. Asked why “SNL” hadn’t cast many Black women, Thompson said, “It’s just a tough part of the business. Like in auditions, they just never find ones that are ready.”

Thompson says that what he meant to point out was that there also needs to be more representation of Black women in the training grounds that traditionally prepare performers for “SNL,” including improv troupes.

“I would never say anything derogatory towards Black women — like, I would never say Black women aren’t funny or anything like that,” he says. “I would never throw towards my mother, sister, wife, whoever.”

Thompson says last year’s national conversation about police brutality and systemic racism also led him to reassess the ways he can use his voice to effect change.

“Just wanting to be in the fight,” he says. “Having to fight from a distance, because I have to watch my household. But making sure however I can use my platform that I would do that. Trying to put out the fires of extreme frustration and anger and channeling that energy into where it can actually make direct change, or just paying attention to Stacey Abrams in general.”

And that sense of social responsibility also includes playing a role model on “Kenan” while continuing to do everything he does on “SNL.” Despite the busy sitcom schedule, Thompson has no plans to leave “SNL” anytime soon.

“I have a certain number I would love to get to,” he says of how many seasons he’s aiming for. “I think 20 is a good, round, even number that I’m close to. I feel like that is in reach, but also it would be respected if I don’t get there. Like, 18 is fine, 19 is fine. It doesn’t really matter. What matters is, will I have time for my family? There’s only 24 hours in a day.”

Michaels is also fine with allowing his talent to balance extracurricular gigs with the mother ship. (He’s also an executive producer on Aidy Bryant’s Hulu comedy “Shrill,” which filmed in the fall and limited her “SNL” screen time as a result.)

“The industry finally came around to my way of thinking, which is, why does a series have to be 24 episodes, and why do you have to leave ‘SNL’ for it?” Michaels says, adding that he welcomes Thompson’s goal to reach at least 20 years. “And I’m not going anywhere. I’m going to hit the 50-year mark soon, so it’s good.”

Thompson, meanwhile, is already looking at his next bridge — producing. He was a producer on Nickelodeon’s recent “All That” revival, and now he’s got more ambitious plans.

“I left DreamWorks today doing a voiceover for a ‘Trolls’ holiday special that’s coming out later this year, and just walking around the DreamWorks campus, it’s the most massive thing that’s employing all of these different lives and really making a mark on people,” he says. “Now that I’ve achieved what I’ve achieved, if there’s any kind of a way to put down a steppingstone that’s a little smoother than the one that’s there, then I feel it’s my obligation to do so. So that’s kind of my approach to producing. I have a lot of ideas up in the air, and it’d be nice to pull them down into realities for people. That’s what I’m working toward.”