Jordan Strauss/Invision/AP
May 07, 2017 03:53 PM

Kenan Thompson is about to make history.

The comedian, actor and writer is approaching his 15th season on Saturday Night Live, which will officially make him the longest-running cast member in the show’s history. Over the years, he’s delighted fans and audiences with his off-the-wall impersonations, his unique characters and his ability to make any sketch he’s in funnier simply by reacting to what’s going on around him.

“Sometimes you don’t even have to write him lines,” SNL head writer Bryan Tucker told Slate in 2014. “This past season, Kenan had everyone laughing at our Wednesday table read just by interpreting stage directions: ‘KENAN ACTS OUT ‘PRICE IS RIGHT’ THEME’ or ‘KENAN FAKES SIGN LANGUAGE BEHIND THE PRESIDENT’ or just ‘KENAN DIES.'” Costar Will Forte echoed that sentiment to The Huffington Post: “He’s the person who can steal a sketch with not even a word ― a cock of the eyebrow.”

In celebration of 15 years of his comedic talents, we’ve rounded up 15 of Thompson’s best SNL moments. And yes, you will be singing “What’s Up With That?” for the rest of the day.

1. David Ortiz Announces His Retirement Plans 

An impression so ridiculous and hilarious that even the real Big Papi himself couldn’t help but play along. Although, for the record, we’d totally eat a big lunch and then work out at Iguananox with Thompson.

2. The Parole Board

A strange, wonderful sketch about a cannibal who’s pleading his case to the parole board — but who would also totally give up rehabilitation in favor of getting to eat just one more person.

3. Live Report 

Need proof that Thompson can deliver every single line perfectly? Listen to him exclaim “She’s a Kennedy … and she put a Shatt on it!” and try not to laugh.

4. What’s Up with That? 

Sing it with us now: Ooooo Weeee! What’s up with that? What’s up with that?

5. Steve Harvey Hosting Family Feud 

To be fair, those are some pretty fly suits, player.

6. Yo! Where Jackie Chan at Right Now? 

Two Jackie Chan superfans just really, really want to know where he is — even if they don’t totally know who he is beyond the fact that he “was in movies and also karate.”

7. Kenan Thompson as Charles Barkley

Thompson’s impression of Charles Barkley might not be the most accurate one that exists, but the mock turtleneck-wearing, seafood buffet-eating, constantly gambling version that he portrays on SNL is definitely the most hysterical.

8. President Obama After Nelson Mandela’s Funeral 

As the fake sign language interpreter that signed at Nelson Mandela’s funeral, Thomspon brings his signature goofiness to a truly absurd situation.

9. Mokiki 

Look, we can’t explain this sketch, we just know that we love it. Maybe we, too, have been hypnotized by the Sloppy Swish.

10. Michael Che’s Neighbor, Willie 

As Michael Che’s perpetually optimistic — or possibly delusional — sad sack neighbor (who may or may not have worked for Jeffrey Dahmer as a child), Thompson brings a dose of truly strange sunshine to every Weekend Update he appears on.

11. Dan and Didi Sing a Tribute to Their Late Friend 


Thompson and Scarlett Johansson bring the house down as two New York club kids who pay tribute to their dear, departed dentist friend with the filthy bangers that he secretly wrote. It’s the perfect mix of absurdity, awkwardness and weirdly catchy deep house music.

12. Jingle Barack 


How did you celebrate Christmas 2016? Because Thompson and Chance the Rapper teamed up for an update of “Christmas in Hollis” for the last holiday that Barack Obama was still president.

13. Black Jeopardy 

A true classic of the “fake game show” genre.

14. Romance Bookstore 

Even when he’s playing the straight man — in this case, the exasperated owner of a romance-themed bookstore who has to deal with his employee and her stock boy acting out their bodice-ripper fantasies at work — Thompson manages to be the funniest one in the sketch.

15. Stranger Things 

To be fair, where were his parents?

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