Kenan Thompson took the stage in an oversized three-piece suit and an awkward wig bursting with Jheri curls. He looked, objectively speaking, completely and utterly ridiculous.
Seconds before, a BET logo flashed across the screen as SNL cast member Will Forte, playing a talk show announcer, introduced the sketch: “It’s ‘What’s Up With That!’ Tackling the issues of today with soul,” Forte bellowed. “Now, here’s your host: Diondre Cole!”
It was October 17, 2009, and unlikely as it seemed, Thompson was finally about to have his moment with the debut of a Saturday Night Live skit that would define him.
He boogied in with a silly zip to each step. Perfectly in time, perfectly in tune and perfectly in control, Thompson began to sing, “Ooo―eee! What up with that? What up with that?” along with his two go-go dancers, played by Nasim Pedrad and Jenny Slate.
What, exactly, was happening? Almost no one seemed to know, most especially the bewildered guests of the fictional show, which included James Franco played by James Franco, Abby Elliott as a famous environmentalist and, inexplicably, the Fleetwood Mac guitarist Lindsey Buckingham performed by Bill Hader.
Eventually, the music stopped, and Thompson took a seat next to his guests. Behind him rested a candelabrum with three unlit candles. Nothing about what was happening made sense, but Thompson looked calm. “All right!” he yelled. “This is ‘What’s Up With That.’ We’ve got three wonderful guests here joining me. We’re going to talk about people.”
Before he could get in another word, a high-hat started playing in four-four time. Suddenly, Thompson’s eyes widened. He turned to his guests with a mischievous smile and a boyish excitement. His words took to the rhythm of the beat.
“We’re going to talk about places,” he continued. “We’re going to talk fingers. We’re going to talk about faces.” Then, he worked with the horns, which had also joined in. “We’re going to talk about things pertaining to you, and you, and you, and you, and you. You too! Not you, but you and you. Everybody sing!”
Just like that, a gyrating Thompson was in the audience ― leaving behind his bewildered guests ― the go-go girls were back at it, and a dancing Jason Sudeikis had appeared on stage in a red Adidas jumpsuit with an enormous gold chain around his neck. Fred Armisen was there, too, with a curly Kenny G-style wig on his head and a saxophone in his hands.
It was a hypnotic, confusing mess. Why was a Fleetwood Mac guitar player appearing on BET with James Franco and an environmentalist? Why weren’t they talking? Had we missed something ― a previous version of the sketch, perhaps? What was the point? But for some unexplainable reason, it was funny.
To many viewers, SNL is most memorable in seasons like the current one, when national elections lead us back to the show on NBC to make sense of the world around us. But to the people on stage at that moment, this was the show at its best ― a sketch based around the absurd outer reaches of their collective imagination, not the political windings of the week. And Thompson was the maestro orchestrating it all.
After almost a lifetime on television, Kenan Thompson might be on a first-name basis with the general public, but he doesn’t come close to registering as one of the most famous people to walk through the doors of 30 Rockefeller Plaza. His time on the show has never translated into Hollywood stardom or his own TV show. Even at SNL, there has always been someone else who took the title of favorite ― a Tina Fey, or an Andy Samberg, or a Kristen Wiig, or a Kate McKinnon.
But quietly, Thompson, who joined the cast in 2003, has strung together a run at SNL that will soon be without precedent.
Should he return next fall for another season, Thompson will make SNL history, becoming the single longest-running cast member ever at 15 seasons.
The Huffington Post spoke with a dozen current and former SNL writers and cast members for this story. What emerged is a portrait of excellence, and of a man who has mastered a set of skills that many of his peers feel have not gotten enough recognition.
What makes Thompson special is not best utilized in movies, or on a pre-recorded sitcom, or behind a desk ― but right there, live on air at 11:30 p.m. on Saturday night.
“If you were designing the person perfect for SNL, most of the components would look like Kenan,” Lorne Michaels told me in a phone interview earlier this year.
Thompson makes everything at SNL better. The writers can rely on him to bring them back a laugh. The cast members know that he’ll set them up for their own moment. And the crew members know that they’ll have someone who will act as an on-stage director, controlling the tempo of the sketch and the people around him.
Back in 2009, however, when he walked on stage as Diondre Cole for the first time, Thompson felt anything but perfect. By then, it had already been six long years since he had joined the show, and many of his peers had long ago established themselves with signature characters. Hader had Vinny Vedecci. Kristen Wiig had the Target Lady. Andy Samberg had his pop star persona in his digital shorts.
Thompson had a few minor hits here and there, like “Deep House Dish” and “Scared Straight.” But by and large, he had yet to find a niche on the show. A couple of times early on, he even “donuted,” a phrase used by SNL cast members to describe when someone doesn’t appear on camera a single time in an episode.
In person, Thompson is soft-spoken, polite and reluctant to talk about himself. When we met at at a restaurant near 30 Rock one afternoon in January, he wouldn’t even eat his chicken wings until the official interview had ended for fear of seeming rude. During our conversation, he admitted that he quietly struggled with himself during those early years at SNL.
He couldn’t find his voice, and the situation led to panic and uncertainty. He had difficulty watching himself on screen. In a moment of frustration, Thompson said, he asked his manager, “Why you even got me on this fucking show?”
Later, he would realize “donuting” is rather normal for young players. But for a while, it left him feeling self-conscious, especially considering an awkward truth: He was different from the people around him. He hadn’t arrived by way of the improv world of Second City or The Groundlings, nor as an up-and-coming comedian in the stand-up scene, like most other cast members. He was Kenan Thompson, former child star of Nickelodeon’s “Kenan & Kel” and “All That.”
His time at the children’s network had helped get him to SNL, but it also led to insecurity once he was there. He had trouble getting work after leaving the network, and privately started to fear people would never see him as anything more than one part of a comedy duo.
“People made it seem at first like we couldn’t do anything without each other, like we weren’t funny individually,” Thompson said. “Kel and I, we both decided that we wanted the world to know that there was a Kel Mitchell and a Kenan Thompson.”
At SNL, Thompson did what he could to reshape his image. He became close friends with Bryan Tucker, who joined the show as a writer in 2005. Once, Tucker, who is now a co-head writer on the show, asked Thompson if he would be willing to pair up with another cast member for a sketch. Thompson agreed, but in a moment of vulnerability, he admitted to Tucker that he wanted to do something by himself.
“I think he was just trying to forge his own road,” Tucker said. “Especially early, he hoped to make his mark as an SNL star, not as a guy who you used to watch on cable.”
It would take time. To other people at SNL, Thompson clearly possessed a knack not only for memorizing his written parts, but calmly delivering them so consistently that he would become a safeguard for the writers on the show. He also enjoyed a comfort on stage that he had been building since his Nickelodeon days, and an ability to play any number of small parts on short notice. But what, exactly, did he do better than anyone else? Even he wasn’t sure.
“The first couple years, [I was] just panic-stricken, not knowing if I’m doing good or not knowing if I’m making an impression or the right impression,” Thompson said.
So he made himself essential in other ways. Behind the scenes, his kindness became a calming presence. “It’s a real hard job,” former cast member Darrell Hammond admitted. “I looked for him every day just to talk, just to shoot the shit about something. He made me feel good.”
But after six years of working at SNL without ever quite thriving in it, Thompson finally found something in “What Up With That.” It was bizarre and disorganized and unlike anything else on the show. And it was a hit ― and his hit to boot.
“Once it happened once, I was like, ‘Oh, this is a great formula,” Thompson said. “Then when we did it the second time, I was like, ‘Oh, I can do this.’”
“What Up With That” gave Thompson confidence, and it gave SNL writers an understanding of his greatest strength: his ability to act as an on-stage director, calmly and selflessly pulling the most out of the people around him amid confusion.
“He’d make me look funny,” said Hader, who would return as the always-silent Buckingham many more times. It was a generosity multiple cast members mentioned.
But Thompson, Hader said, had another weapon. Unlike most of the show’s actors who might have pre-performance jitters, Thompson was never nervous. Instead he’d mess with other actors seconds before they went on air, sending them on stage with a laugh and an air of confidence. He watched sketches when he had free time, offering words of encouragement when something fell flat. And on stage, Thompson didn’t compete. He facilitated.
When I told Thompson how often his peers brought up “What Up With That” as being one of their favorite skits, he brushed it off with a joke. “I love a good party!” he laughed. But later on, his willingness to put the sketch above himself became clearer.
“I just love for the sketch to go right,” he said. “If I’m involved in it and it’s my thing, it has to be right.”
Inside SNL, Thompson’s innate understanding of sketch comedy, built over a lifetime of practice, has become an anchor for the show, providing a steadiness that can be hard to come by, even among the world’s best comic actors.
In January, Tina Fey, dressed as Princess Leia during a guest appearance, told host Felicity Jones, “If all else fails, you should know that back in Season 35, I put a fatal flaw in the system: If you take out Kenan Thompson, the studio will explode.”
The ability and willingness to adapt on the fly to the writers’ desires is one of the most important skills a cast member can acquire, and it’s what makes Thompson indispensable, Hammond told me. And boy can he adapt. According to the SNL fan site SNLarchives.net, he has already impersonated well over 100 people during his time on the show, more than any other cast member in the show’s history. He’s played Al Roker, David Oritz and Cee Lo Green, as well as Tyler Perry, Whoopi Goldberg and Sway. He has also played Sir Mix-a-Lot, Maya Angelou and Neil deGrasse Tyson.
“He’s a thing that almost doesn’t exist anymore, which is: He’s a variety performer,” Lorne Michaels said. “He can sing. He can move. He can do comedy, and he knows who he is in front of an audience.”
SNL is currently enjoying its most successful season in more than two decades, thanks in large part to the near-constant material provided by the election of President Donald Trump. But James Andrew Miller, author of “Live From New York: The Complete, Uncensored History of Saturday Night Live,” noted that SNL needs to survive in years when political news is slow, too.
That’s where Thompson comes in, he said. While many others have made their name with political impressions, Thompson began to make his through what Miller described as “the blocking and tackling of the show — bringing memorable characters to life who aren’t connected with topical news, but are flat out funny,” with spectacular moments like this year’s David S. Pumpkins bit, or driving a Family Feud sketch as Steve Harvey.
Then, there is that look. You know the one: A wide-eyed Thompson turns towards the camera as it zooms in ― the closest thing humans have produced to a real-life cartoon character. “He’s the person who can steal a sketch with not even a word ― a cock of the eyebrow,” said Will Forte, who joined the show one year before Thompson.
SNL writers would also come to understand the power of that look. When they expected a sketch to lean a tad weak, the writers learned to tuck in a “KENAN REACTS” line to the script. It can easily wrap up a joke, but it also does something else: It allows the audience to feel as if they have a friend on stage, someone they can relate to even if they’re alone on Saturday night.
As Forte explained it, “I would imagine people watching must feel like he’s one of their buddies, or family members.”
Thompson’s understanding of what makes a great sketch, and his ability to improve it on the fly, slowly became a source of amazement among writers and cast members alike.
“There are times when the director will have the wrong shot and Kenan, in real time, will be pointing to the other camera just instinctively knowing how shots should go,” said Colin Jost, a current co-host of “Weekend Update.”
Thompson has found a unique niche on stage in the bizarre, silly world where “What Up With That” lives. But when the camera stops rolling, he plays a role on the show that runs almost counter to his on-screen persona: that of the mentor.
He tells new insecure writers when they wrote a good joke. He watches new cast members from the side of the stage to give them a vote of confidence. “He’s so supportive,” said former SNL writer Tim Robinson. “He’s always the first to give it up.”
When Leslie Jones arrived in 2014, she was already a fully formed stand-up comedian. “I thought I was the funniest motherfucker that lived and nobody could tell me different,” she said. But Jones found herself feeling frustrated by the the show’s rules and more laborious requests.
The time-consuming pre-taped segments, in particular, bothered her. Eventually, Jones told Thompson she didn’t want to do them anymore. “How are you going to sit here and say you aren’t going to do pre-tapes anymore?” Jones recalled him asking her. “You’re part of the cast. Yes, you are, and don’t come in here telling me that you’re not.”
Jones credits Thompson’s insistence that she take all aspects of the job seriously, from the pre-taped segments to the table reads, as one of the main reasons for her success on the show. “I don’t think I would have took the place the way I was supposed to take it if it wasn’t for him,” she said.
Jones owes her career at SNL to Thompson in more ways than one. On Oct. 14, 2013, TV Guide published an interview with him in which he announced that he would no longer play black female characters on SNL, which had lacked a black female cast member since Maya Rudolph left in 2007. When asked why the show hadn’t hired a black female member since Rudolph, Thompson replied, “They just never find ones that are ready.”
TV Guide took the soundbite and ran with it, entitling the piece, “Kenan Thompson Blames SNL’s Diversity Issue on Lack of Talented Black Comediennes.”
Just weeks earlier, fellow SNL cast member Jay Pharoah had told a reporter for the black news site The Grio that he was unhappy that the show lacked a black female cast member. The two events together led to the largest controversy of Thompson’s career.
Black female comedians created a video entitled “WE ARE READY!” to protest his comments. Color of Change, a racial justice organization, demanded Lorne Michaels address his show’s lack of diversity. Jones, who didn’t know Thompson at the time, made her anger known too at a Los Angeles comedy club called Inside Jokes.
“He should come battle me,” Jones reportedly said. “Give me ten minutes and I’ll ruin his life.”
The situation upset Thompson. Non-confrontational almost to a fault, he continues to insist that he was quoted out of context, and that he did not mean to imply there were no adequate black female comedians at that time. But as a result of the TV Guide article, Michaels held a special audition for black female comedians less than two months later, which led Michaels to hire Sasheer Zamata as a featured player and LaKendra Tookes and Leslie Jones as writers. (Jones would later make the transition to cast member.)
Thompson’s comments briefly hurt his reputation, but ultimately they helped to diversify the racial makeup of the show. He’s fine with that tradeoff. “If I was the villain of that whole thing, I don’t really care,” he says now. “Because at the end of the day, Leslie is my homie, and Sasheer is my homie, one of the sweetest people I know, and LaKendra got her shine.”
SNL remains largely white and male. But with Thompson, Jones, Zamata and Michael Che all on board in Season 42, and Melissa Villaseñor joining as the show’s first Latina featured player, there’s reason to feel optimistic that Michaels is getting serious about diversifying the cast.
“It’s just cool to see walls getting kicked down while I’m there,” Thompson said, adding jokingly, “It’s an epic time for black people on the show.”
He dismissed the idea that he had a role in the show’s increasing diversity, instead pointing out that Che is the first black man to host “Weekend Update.” “He broke down real barriers,” he said. “He should be on the cover of Ebony like almost every week!”
But in his own way, Thompson has done what he can at SNL to make sure black Americans are better represented on the show. Bryan Tucker said Thompson has taken the time to patiently explain that diversifying the show isn’t beneficial because it silences public pressure but because “making these hires and doing this allows us to have this whole new perspective on things ― opens up new doors of the show.”
That was clear last last October, when host Tom Hanks joined Zamata, Jones and Thomp on stage as a rural Trump supporter for a sketch called “Black Jeopardy.” The sketch connected the political concerns of white Trump supporters and African Americans in a way that few journalists or politicians could do in the months leading up to Trump’s election, and it quickly became one of the most talked about moments of the season.
When will Thompson decide to leave SNL? Darrell Hammond, who is tied with him for longest run on the show, decided that his time was nearing after he didn’t win a role portraying anyone in the Obama administration. Tim Meadows, who held the record before Hammond, said that after a decade, “I kind of felt like at a certain point, you have to sort of give somebody else a shot.”
Should Thompson want to return next season for a record 15th season ― and he says he does ― he’ll be welcomed back. “I dread the day when he actually leaves,” Michaels said. “I would have him back for the next 20 years if I could figure out a way to keep him.”
It sounds like he will. Thompson has thought about leaving at times, but famous as he is, he knows he isn’t a movie star, and he isn’t a stand-up comic, either. He’s a sketch comic actor — one that has finally distinguished himself as the singular comedic force he wanted to be.
This season, only Kate McKinnon is more popular than Thompson among regular viewers of SNL, according to a HuffPost/YouGov poll conducted in December and January.
“I thought that SNL was just going to be that bridge into being an adult actor,” he said. “They’ve not only been a bridge. They’ve been a fucking highway for me.”
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