“As you can see, we’re in here with no windows, so you kind of get trapped in a bubble,” says Kenan Thompson, the longest-serving member of the cast of Saturday Night Live in its 43-year history, as we sit down in his cramped dressing room at 30 Rock, to record an episode of The Hollywood Reporter‘s ‘Awards Chatter’ podcast. He continues, “You look up — and it’s 15 years later. That shit is crazy!” Thompson, a former child star who is now 40 and married with a young child of his own, rarely grants interviews, preferring to keep a low profile. But near the end of his 15th season with TV’s most fabled variety show — at that season’s start, he surpassed Darrell Hammond‘s record to become its longest-running castmember — he agreed to look back on his life before and during SNL, and to speculate about what it might look like when he eventually leaves the show.
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Thompson was born in Columbus, Ohio, but raised from an early age in Atlanta. He first performed in church and in school, drama as often as comedy, and found that, unlike piano-playing and sports, “Acting was always the one thing I never wanted to walk away from.” As a result, he was enrolled in a program that helped child actors find their first agent, and then landed on TV for the first time at just 10. “I got the bug off that fried chicken commercial,” he recalls with a laugh. He also studied with the Youth Ensemble of Atlanta, a nonprofit youth training program. Auditions first began paying off for Thompson when he landed the job of a film critic for a kids news show on Atlanta-based TBS at age 12. Shortly thereafter, he won a part in D2: The Mighty Ducks, which he calls “my first Hollywood gig.” And then the director of that film introduced him to the producing team of Brian Robbins and Mike Tollin, who cast him, at age 14, on Nickelodeon’s new primetime sketch comedy show All That. That opportunity, which involved relocating to Orlando, was, Thompson says, “more than I could have dreamed,” emphasizing, “Most black kids aren’t, like, doing TV shows.”
The show quickly became a staple of “Nick at Nite” programming, beloved by kids of all ages and races. “We were like, ‘We’re the SNL for kids,'” Thompson recalls with a laugh. After the first season, Thompson and another standout from the show, Chicago-born Kel Mitchell, were approached by Robbins and another producer, Dan Schneider, about shooting a pilot for a spinoff show, Kenan & Kel, which they would potentially make on top of doing All That. The two youngsters were thrilled and became fast friends even before the new show was ordered to series. “Kel and I were always really close because we’re super similar,” Thompson explains. “He was just really cool.” When Thompson and Mitchell turned 18, both All That and Kenan & Kel relocated to Los Angeles, which meant they moved, too. Thompson tried performing stand-up on the side, but never felt comfortable and instead became a regular consumer of it at comedy clubs. In 2000, when he and Mitchell were both nearing their 21st birthdays, their contracts came to an end, and neither extended. “I was just feeling like, ‘You can’t be on Nickelodeon forever,'” Thompson explains. “I got to the ceiling of the kids’ world.”
The next few years were among the most challenging of Thompson’s life. “Breaking through to the adult world was kinda like starting from scratch,” he says. “It started becoming a real hustle.” After a few years of struggling to land meaningful work — with a few exceptions, like a four-episode guest arc on The WB’s Felicity — he began to feel not just professional frustration, but also financial strain. “Nickelodeon earnings started running short, and shit got real,” he acknowledges. But then, as he sees it, he caught a lucky break. In 2003, Tracy Morgan and Dean Edwards, both black performers, left SNL, so the show sought at least one new black male performer, and Thompson’s representation, citing his history in sketch comedy, got him an audition. “It was a black casting call,” he says. “I can’t front on it. We were all black.” At the first audition, Thompson ran into someone else he knew who was also vying for a spot on the show: Mitchell. In the end, after a drawn-out audition process, Thompson was hired and Mitchell was not. “I didn’t see him again for a couple years more down the line,” Thompson recalls, noting that their lives took “two different paths.”
When Thompson got the job in 2003, he had to move almost overnight to New York. The youngest member of the season 29 cast, and the first SNL castmember ever born after the show itself debuted in 1975, he struggled to figure out his place on the show. As he puts it, “I was happy, but I wasn’t in the show much,” adding, “I got donuted [totally left out of an episode] a couple of times.” The root of the problem, he eventually realized, was that he wasn’t a writer, and none of the people who were writers were particularly looking out for him. “I had never had the writing responsibility before — at Nickelodeon, they wrote everything, and our job was to take it and make it funny,” he explains. For things to change, Thompson realized, he would need to learn how to write his own material and/or a writer would have to take a special interest in him.
Both things eventually happened, the former with the passage of time, and the latter with the arrival, in 2005, of Bryan Tucker, a “very white” man who was infatuated with black culture. Thompson remembers, “I was saying to myself, ‘He can definitely help me get this craziness out of my mind and make it make sense.'” And, sure enough, that’s what happened. On Oct. 17, 2009, Thompson performed his first-ever “What’s Up with That?” sketch, which he had co-written with Tucker, and it was a smash. It marked a turning point for the young actor, who began to find his comfort zone doing non-topical skits (not ripped-from-the-headlines stuff) and impressions (Hammond held the record for most ever done on the show with 106 until 2014 when Thompson passed him; Thompson is now up to 126, standouts of which include Steve Harvey, Rev. Al Sharpton, Dr. Neil DeGrasse Tyson, David Ortiz and LaVar Ball).
Thompson has survived since 2003 — and thrived since 2009 — at SNL largely because he has won the respect and admiration of his boss, Lorne Michaels, and his peers, past and present, with his hard work and versatility. He describes himself as a “big-time team player type of dude,” but jokes about why that may be: “I need people. If I was able to sit down and type a sketch all by myself, I might be more of a dick. But I’m humble enough to know that I do well when I’m working with others.” It was this innate humility that also led Thompson to “feel a little guilty” as he approached the SNL tenure record long held by Hammond, alongside whom Thompson worked from 2003 through 2009, and again since 2014, when Hammond returned to the show as an announcer. “I always had a Yoda-type relationship with him, and he reciprocated that,” Thompson volunteers. “When I started approaching the record, I was like, ‘Man, that’s crazy.’ But he was always cool about it. He was like, ‘Comin’ up on that record, huh?’ I was like, ‘Yeah.’ And he was like, high-fiving and patting me on the back.”
How much longer will Thompson remain with SNL? As far as Michaels is concerned, he can stay forever — but Thompson realizes that won’t really be possible. “I think about leaving and I fear it,” he confesses, “just because I know it’s never gonna be the same. It sucks because this is such a special place.” He continues, “You also want to make room for people that are coming behind you. This was the first year I really started feeling like, ‘OK, I can kind of push out of it now,’ because Chris [Redd] came in and he’s super-duper strong. I really look forward to his potential on the show. That was the first time I was like, ‘Maybe I should position out to give this dude more room.'” He adds, “It’s good that they got an extra [black male performer], but Chris kinda can do all of that stuff, and now it’s like, ‘Well, if that’s the case, then yeah, it might be time to move on or whatever.'” That’s an interesting thought — but does Thompson actually have any plans to depart? “Not really,” he deadpans. “I’m not overly excited about going back to auditioning.”