On the night of October 4, 2003, twentysomethings everywhere were delighted to see that Kenan Thompson, one of the most prominent players on Nickelodeon's All That back in the '90s, had hit the big time. Along with Finesse Mitchell, Thompson joined the cast of Saturday Night Live as a featured player. Unlike Mitchell, he never left.
Thompson now holds the distinction as Saturday Night Live's longest-tenured cast member, and he still has a healthy attitude about his role in the ensemble. "I’m just out there trying to be joyous, basically,” he once told Vanity Fair. Nineteen seasons in, he's still going strong — even while juggling his own eponymous NBC sitcom
Over the last two decades, Thompson has portrayed an array of recurring favorites. Here are ten of his best — and yes, narrowing down 18 years of work was a challenge!
When casting for the role of Reba McEntire, you might figure that Thompson would be the last choice. But he's absolutely perfect. Thompson showed up to play Reba in the Lonely Island short "Two Worlds Collide" back in 2009. The question of the video: is this Reba McEntire real, or just a homeless man in a red wig that Andy Samberg happened to connect with in a dressing room? The song is absolutely ridiculous, but it's almost impossible not to belt out "I'm Reba!" after you watch it.
Thompson can't have known that his Diondre Cole, host of the mock-talk show "What Up With That?" would be such a hit — but even though every "episode" has unfolded in maddeningly similar fashion, it's always brought laughs. Thompson had a dedicated ending to the recurring sketch back in 2012, but he's brought it out out of retrirement three times since to the great delight of everyone (no one moreso than Bill Hader's Linday Buckingham.)
Reese De'What is one in a series of recurring SNL characters who get most of their laughs based on the ridiculousness of their names. De'What helps lead a PBS broadcast called "Cinema Classics." The popular Saturday Night Live sketch has run since 2013, with Thompson's pronunciation of "De'What" becoming more pronounced as the years went on.
If there's one upside to the omnipresence of the real Steve Harvey, it's that he's given Thompson a lot of airtime over the years. Thompson's most common Steve Harvey impersonation has been in Family Feud sketches, which not only get a laugh, but utilize a ton of cast members for celebrity impersonations. Still, it's hard to forget the "Phobias" skit he did back in 2013. Or should we say, Pho-Bias.
It's easy to mix up Jean K. Jean with Thompson's All That character Pierre Escargot. Both are French — but while Escargot spends most of his time in a bathtub, Jean K. Jean, a Def Jam comedian, feels more at home behind the Weekend Update desk. The character first debuted in 2008, and Thompson kept him going until 2013.
Saturday Night Live fans don't all love this recurring skit titled "Last Call," but it's hard not to chuckle over Thompson's shocked and surprised reactions. Even when you know they're coming, they still add so much to the sketch. Plus it's always delightful to watch him interact with Kate McKinnon.
Thompson's relationship with Bill Cosby has changed a lot over the years. Thompson played the lead role in Cosby's film Fat Albert back in 2004, so he treated the fallen icon with respect early on. But when news broke of Cosby's sexual scandals, that all changed. One of his most recent Cosby impressions was back in 2018, when he played Seth Meyers' cell mate.
The Reverend Al Sharpton has been on the show himself. But when he's not, he's being impersonated by Kenan Thompson, who officially took the role from Tracey Morgan back in 2004. The best part? Sharpton and Thompson are familiar with each other off-screen, and Sharpton doesn't mind it one bit. "People ask me and I think it’s nothing but fun,” Sharpton said on his show Politics Nation in 2015.
When Whoopi Goldberg signed on to help sell Poise pads back in 2010, Keenan Thompson was there to talk about it in character on Weekend Update. It makes sense that Thompson has stopped playing female characters as the cast has became more diverse, but this impersonation was so strong that it's hard to imagine anyone playing her better.
Finally, let's talk about Star Jones. While Star's star doesn't burn quite as bright these days, Thompson portrayed the former View co-host before her wedding day, with Finesse Mitchell playing her groom, Al Reynolds. While Thompson didn't get to belt out any lines like Tracy Morgan's famous "I am a lawyer!" from years prior, he did a great job. Which should come as no surprise to anyone who's followed Kenan Thompson for all these years on SNL. He's been as dependable for a laugh as anyone who's walked on that stage.
What did we miss? Which Kenan Thompson SNL characters are your favorites? Weigh in on our forums.
Karen Belz has contributed to sites such as Bustle, HelloGiggles, and So Yummy. Follow her on Twitter at @KarenEBelz.