Kenan Thompson is this week’s guest on ‘Masters of the Game’

OPINION: The comedy legend talks about what makes him a successful comedian.

Kenan Thompson at the 2022 theGrio Awards. (Photo by PurplePPL Media)

Editor’s note: The following article is an op-ed, and the views expressed are the author’s own. Read more opinions on theGrio.

Kenan Thompson is my guest this week on “Masters of the Game” on theGrio TV because he’s an extraordinary comedian. He’s the longest-tenured “Saturday Night Live” cast member of all time because he’s hysterical. People on that show know that if you put him in a sketch he’ll make it better. And, I noticed, in my research, he’s not just in most of the sketches, he often plays a leader in the sketch. Thompson is often the game show host or the judge in the courtroom or the father figure. I think this is a reflection of how the people who are writing and creating the show see him as a leader onstage and off. We had an interesting talk about that.

Thompson was definitely a leader in 2013 when he asked “SNL” to stop putting him in dresses to play women, and hire Black women cast members. Before that, it was common to see him playing Maya Angelou or Whoopi Goldberg. I was very impressed by that move, and I wondered how that had played out. Was there a tough conversation with “SNL’s” executive producer Lorne Michaels? We talked about how, and why, he took that stand. It spoke to years of lacking Black women in the cast. In its first 38 years, there were only four Black female cast members: Yvonne Hudson, Danitra Vance, Ellen Cleghorne and Maya Rudolph. In the years since Thompson’s stand, the show added Sasheer Zamata, Leslie Jones, Ego Nwodim and Punkie Johnson. Thompson made a difference. We talked a lot about that.

Thompson was a really easy person to interview. He came on time. He was alone, and he exuded a warm vibe. He’s humble, unassuming and gentle. There was no ego or sense that he was a big TV star. Part of that, he said, is that he’s a professional. He’s been working in front of the camera since he was a teenager. He was an entertainment reporter for CNN’s “Real News for Kids,” and he starred on two shows, “All That” and “Kenan & Kel.” Because of his years in entertainment, he views his work as a job, not a star turn. And he’s a craftsman. 

He knows how to make something funny. Nowhere, to me, is this more evident than in his recurring sketch, “What’s Up With That?”, where he’s the host of a show that never really gets started. He keeps jumping into the theme song over and over. “SNL” has done “What’s Up With That?” many times, and every time it’s pretty much the exact same script. The first time I saw it I thought it was funny. The second time, I thought, “That’s weird. They did the exact same sketch which is, itself, repetitive. That’s weird.” The third time, I got it. The endless repetition is the gag. It’s a much more abstract joke than you usually get on “SNL” and, really, only Thompson could pull it off. His particular brand of silly is just right for that. We talked a lot about his “SNL” sketches and how he made them work.

“Masters of the Game” is a show about talking to the greats and finding out what makes them great. We definitely get down to the reasons behind the genius of Thompson just as prior episodes gave us a look into the genius of Debbie Allen, Frances Tiafoe, Doc Rivers, and others. Check out “Masters of the Game,” hosted by Touré, on theGrioTV.


Touré is a host and Creative Director at theGrio. He is the host of the podcast “Toure Show” and the podcast docuseries “Who Was Prince?” He is also the author of seven books including the Prince biography Nothing Compares 2 U and the ebook The Ivy League Counterfeiter. Look out for his upcoming podcast Being Black In the 80s.

TheGrio is FREE on your TV via Apple TV, Amazon Fire, Roku, and Android TV. Please download theGrio mobile apps today!