As Saturday Night Live enters its 48th season, Kenan Thompson continues his reign as the longest-tenured cast member in the show's history. Thompson joined the show in 2003, following a successful career on the Nickelodeon sketch show All That, as well as the sitcom Kenan & Kel and the wildly-popular movie Good Burger, alongside Kel Mitchell.
In his 20th season on the NBC late-night program, Kenan continues to be one of the show's most seasoned and capable cast members. He still carries iconic sketches, whilst simultaneously playing a supporting role for newer players. However, these ten sketches from Kenan's time on the show are some of his most memorable performances.
10 First Date
Oftentimes, Kenan excels in sketches that are based on current events. By the time Gal Gadot hosted in 2017, her episode coincided with the recent news of O.J. Simpson's impending release from prison. Famously, the former running back allegedly murdered two people, creating one of the most talked-about trials of the 1990s.
In this sketch, however, Gadot plays a woman who is oblivious to O.J.'s history as she goes on a blind date with him. Kenan does a great job playing a coy Simpson, alluding to his past while also keeping a friendly demeanor for the date. Nothing beats the sketch's reveal of Kenan's identity, as well as his further attempts to avoid discussing his infamy.
9 Two Worlds Collide
Through the late 2000s and early 2010s, Saturday Night Live was ruled by The Lonely Island: a comedy trio consisting of cast member Andy Samberg and writers Akiva Schaffer and Jorma Taccone. The trio was responsible for ushering in an era of SNL with Digital Shorts, airing songs or sketches created independently of the week's production.
One of these songs, "Two Worlds Collide ft. Reba McEntire," follows Andy Samberg as he describes his romantic tryst with country superstar Reba McEntire. The only problem is, McEntire is played by Kenan, who insists throughout the song that she's actually a man in a wig taking advantage of Samberg, who remains hilariously oblivious.
8 Eternal Spark Of Love: Office Romance
This recurring sketch would play on tropes of two people falling in love, with Kenan interjecting as a smooth-talking narrator. However, the idiosyncracies in each of the lovebirds would begin to stand out, with Kenan's character getting more and more creeped out. It was a great example of a sketch that knew how to use Kenan's comedic chops.
The best iteration of it came when Jennifer Lopez hosted in 2010. She and Jason Sudeikis begin to flirt in an office copy room, but Kenan begins to question Lopez's obsession with puppetry. One of the best moments comes when Lopez's character shows off one of her puppets, prompting a silent Kenan to glide across the screen with a horrified expression.
7 Live Report
Margot Robbie's hosting debut in 2016 was one of the strongest episodes in recent years, as the Australian actress threw herself into every sketch. The best example was "Live Report," which featured Kenan as a news reporter investigating a sinkhole. However, he's disturbed when Robbie shows up with her husband, a nerdy man played by Mikey Day.
Soon enough, the entire news report becomes enthralled with how Day's character managed to pull someone as beautiful as Margot Robbie. It gets even more absurd as they discover that Day's character is a puppeteer with no genitalia. Though it's not one of Kenan's showiest sketches, his delivery sells the idea that this man is unappealing.
6 On The Couch
This sketch aired when Daniel Craig hosted in 2020, the final episode before the show was closed due to the COVID-19 pandemic. Before moving to make at-home shows, Kenan got one last chance for a music video alongside Chris Redd and musical guest The Weeknd. Together, the trio sing about being forced to sleep on the couch by their wives.
While the sketch is mostly a great showcase for The Weeknd, who is revealed to be sleeping on his ex-girlfriend's couch to the annoyance of her husband, Kenan's contributions to the song are catchy and humorous as well. It's the type of sketch Kenan excels at in recent years, such as "Come Back Barack" with Chance the Rapper.
5 R. Kelly Interview
One of Kenan's best performances in recent SNL came after a disastrous Gayle King interview with R. Kelly in 2019. In the sketch, Kenan plays the Kelly to Leslie Jones' King, re-enacting key moments from the interview with an emphasis on satire. It's one of Kenan's best impressions, as he perfectly captures Kelly's demeanor throughout the interview.
However, the sketch is obviously not a line-for-line reenactment of Kelly's interview. Numerous times, Kenan insists that he be called "victim," whilst also complaining that no one picked up on the clues to his sex crimes, such as the songs "Trapped in the Closet" and "Age Ain't Nothing But a Number."
4 Family Feud: Harvey Family Thanksgiving
Kenan's impression of Steve Harvey is often a high point of their Family Feud-related sketches. Oftentimes, it's a chance for the other cast members to display celebrity impressions, similar to the Will Ferrell-led Jeopardy sketches. However, this one instance of Family Feud turned the concept on its head thanks to Chance the Rapper.
In the Thanksgiving-themed sketch, Steve Harvey's family competes against their white family friends. However, Steve is oblivious to the fact that one of the white family's sons, played by Chance the Rapper, looks identical to Harvey, down to the suit and mustache. While Kenan shines in the sketch, Leslie Jones also gets points for her character's reaction.
3 Black Jeopardy With Tom Hanks
Black Jeopardy is a recurring sketch where Kenan plays the host, quizzing a panel of guests on several categories related to African-American culture. Typically, the sketch works as one of the three contestants is completely unprepared. However, in this sketch, Tom Hanks plays a MAGA hat-wearing southerner who gets every question right.
Not only is the sketch charming and heartwarming, but Kenan and Hanks do a great job showing the back-and-forth between two people who seem to be opposites. The only Black Jeopardy sketch to rival it is when the late Chadwick Boseman reprised his T'Challa character from Black Panther, but Kenan and Hanks are too good a duo to pass up.
2 Diner Lobster
There was a lot of anticipation from SNL fans when John Mulaney first hosted in 2018. The stand-up comedian was a writer for the show, penning some of the show's greatest characters, like Bill Hader's Stefon. However, hosting the show gave Mulaney the opportunity to bring to life a rejected sketch from his years on the show: "Diner Lobster."
The sketch's big turn comes when Pete Davidson's character orders a lobster at a New York diner. Dejected, Mulaney's waiter calls for the lobster to come out. Kenan makes a grand entrance as the lobster, dressed as Jean Valjean singing songs from Les Miserables. The entire sketch plays out the events of the musical, with Kenan as its tragic lead.
1 What Up With That?
By far Kenan's greatest sketch from his long tenure on Saturday Night Live is "What Up With That?" The sketch debuted during his earlier years, as the host of a talk show where the guests would never get a chance to speak. Instead, Kenan would sing, dance, and introduce absurd characters to sing and dance with him.
The best iteration of it featured a lineup of guests including Robert De Niro, Robin Williams (both real-life actors making cameos), and Lindsey Buckingham (played by Hader, who appears in every "What Up With That"). Kenan's interactions with De Niro make the sketch, with Robin Williams providing some of his classic comedic wit.