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SXSW 'fireside chat': Kenan Thompson thinks Chance the Rapper is a sketch comedy natural

Eric Webb
Austin 360
Kenan Thompson, left, and Chance the Rapper speak at their featured session during SXSW Online on March 17, 2021.

Kenan Thompson and Chance the Rapper are each other's biggest fans, it seems. The mutual praise flowed free and easy Wednesday during the pair's conversation as part of the all-virtual South by Southwest.

Chance on Thompson: You're the "greatest of all time."

Thompson on Chance: “If anyone is a model of how it should be done, it’s you.”

The duo have worked together on "Saturday Night Live," where Thompson is the longest-tenured cast member in the sketch show's long history and Chance (aka Chancelor Bennett) has hosted and performed as musical guest multiple times. Their collabs on "SNL" have earned them two Emmy nominations, one a win (the song "Come Back Barack" in 2018).

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The subject of the SXSW "fireside chat" was Thompson's storied career and transition to sitcom dad with the new NBC show "Kenan." The project seemed like a natural progression from "SNL," Thompson said; he's been a cast member there since 2003. "Kenan" is the third go-round in a development process that's lasted years, he said, and the iteration currently airing has been in the works for more than two years. Fellow "SNL" alum Chris Rock directed the pilot and produces.

Millennial fans go way farther back with Thompson, which Chance was quick to point out. The rapper's favorite show growing up was "Kenan and Kel," Thompson's Nickelodeon sitcom that ran from 1996 to 2000. It was a spin-off of "All That," the cable network's all-kids sketch show that's often compared to "SNL."

"'All That' was, to me and so many other people my age, our introduction to sketch comedy," Chance said, calling the Nickelodeon show "smart, funny and Black."

"The biggest training ground in my life was Nickelodeon," Thompson said of his child star boot camp, because it trained him for what he’s done in his adult career — sketch comedy and sitcom acting.

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Chance asked Thompson if there was a moment as a kid when he realized he was "funny as hell." Thompson demurred but did point out he enjoyed making people laugh from a very young age, and it's how he made friends. He and his brother would quote movies on family road trips back and forth from Lynchburg, Virginia, where their parents were from. Cable TV allowed them to watch their favorite comedies on repeat to memorize dialogue: "Trading Places," "48 Hours," "Coming to America."

A "newish thing" for Thompson's generation of young performers, he said: getting work past the roles that made them famous and avoiding "Leave It to Beaver" syndrome.

"If you were a child star, it was really hard for you to break that for years and years. I didn’t want that to happen," he said. In fact, "Family Matters" star Jaleel White (you might know him best as Steve Urkel) is one of Thompson's "dearest friends," and White deals with typecasting all the time, Thompson said — all people can think of is the catchphrase, "Did I do that?"

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The SXSW chat also provided a behind-the-scenes look at "SNL," which Thompson said is rare: "The camera is only pointed in the direction we want you to see," and only on Saturday. The weeklong lead-up to a live sketch show brings a lot of pressure when you're competing against more than 40 years of indelible pop culture moments that came before you. (Thompson should know, he pointed out; he's been working in 30 Rockefeller Plaza for about 17 of the show's 46 years.)

“It never gets old, because it’s sketch comedy and it changes every week," he said.

The comedy vet had high praise for the younger performer on the other end of the screen Wednesday. Chance said that when he first got to "SNL" for a guest gig, Thompson and former cast member Leslie Jones "smoked me out" and told him to bring his own sketch ideas to the table.

“You didn’t just bring sketches — you destroyed,” Thompson said, pointing out that pretty much all of the rapper's ideas made it onto the show.

To wrap up the chat, the two performers bonded over being family men; both are married and raising daughters. Thompson wanted to depict family life with love on "Kenan." In the show, he plays a widower raising his daughters with his brother ("SNL" co-star Chris Redd) and father-in-law (Don Johnson).

"When I was a single man, my performances would just reflect on me," Thompson said. "Now I have a family and things reflect on my family."