Top 20 Kenan Thompson Moments to Celebrate His 20th Season on SNL
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Top 20 Kenan Thompson Moments to Celebrate His 20th Season on SNL

VOICE OVER: Rebecca Brayton WRITTEN BY: Tal Fox
The past 20 seasons of "SNL" have belonged to Kenan Thompson. For this list, we'll be looking at the longest-running “SNL” castmate's highlights across his landmark two decades on the live comedy sketch show. Our countdown includes "Diner Lobster," "Funeral Service," "Parole Board," and more!
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Top 20 Kenan Thompson Moments to Celebrate His 20th Season on SNL


Welcome to MsMojo, and today we’re counting down our picks for the Top 20 Kenan Thompson Moments to Celebrate His 20th Season on SNL.

For this list, we’ll be looking at the longest-running “SNL” castmate’s highlights across his landmark two decades on the live comedy sketch show.

“De’What” is your favorite Kenan moment on “SNL?” Give us all a good laugh in the comments.

#20: “Live Report”


A reporter, played by Thompson, is sent to a sinkhole site where he manages to bag an interview with two witnesses. Only a tiny detail from their account quickly derails the entire broadcast. Watching Kenan try to make sense of the couple’s relationship is absolutely hysterical. It’s impossible not to laugh when he discovers this stunning woman is a Kennedy who chose to double-barrel with her husband’s unfortunate last name. And who knew that pointing out someone wearing crocs with socks could make us chuckle this much? Thompson does an excellent job of relaying the reporter’s shock and indignation that we almost forget this is just a sketch. It never stops being hilarious.

#19: “Parole Board”


In this kooky sketch, Kenan plays a prisoner who tries to convince a parole board to reduce his life sentence. Only, that’s not exactly the reduced life sentence they have in mind. The sketch is eerily dark, yet Thompson still makes it strangely lighthearted. His comedic delivery is perfect, surprising, and amusing us with every twist and turn. It’s such a bizarre skit that we’re not sure how he got through it with breaking character at least once. Seriously, it’s impressive, given how outrageous many of his lines are. This isn’t one of Kenan’s characters we’d like to meet, but we enjoy watching him on repeat through the safety of our screens.

#18: “Weekend Update: LaVar Ball on His Son LaMelo Ball”


The overzealous, over-enthusiastic, and generally over-the-top LaVar Ball is arguably one of Kenan’s best recurring characters. He never fails to bring laughs and chaos with every Weekend Update appearance. While any Ball sighting is a treat, one, in particular, stands above the rest. On this occasion, he drops by to talk about vaccinations and his son LaMelo’s impressive rookie season. The entire skit is non-stop laugh-out-loud hilarious! Even Kenan and Weekend Update host Michael Che can’t help but chuckle throughout. Thompson’s Ball is simply joy-inducing and so brilliant that he even manages to sell us on his Caramello shoes. You know a character is well played when even those involved can’t stop laughing.

#17: “Two Worlds Collide feat. Reba McEntire”


This musical sketch answers the question: Should country music and rap ever overlap? In it, Kenan plays Reba McEntire, well, kinda, while Andy Samberg plays himself and is besotted with the country icon. The whole thing plays out like a fever dream, with Samberg happily rapping about their relationship while Thompson drops a few truth bombs that Samberg gleefully sweeps under the carpet. We’d have loved to be in the room when they came up with this sketch because it’s truly bonkers. Yet, Kenan’s commitment to the role is outstanding and way too funny, plus his nonchalant delivery of some of the most comical lines is on point. It’s also just a really catchy tune.

#16: “Michael Che’s Neighbor Willie on the COVID-19 Vaccine”


If you need a shot of optimism, might we suggest getting in touch with Michael Che’s neighbor, Willie? Possibly the happiest— or blissfully naïve— man alive. Any appearance from Che's happy-go-lucky neighbor is guaranteed to leave you grinning from ear to ear. In one of our favorites, Willie stops by to talk about the COVID-19 vaccines. Turns out he put in more effort than most of us to find an effective jab, and he’s not too worried about the side effects. Willie’s personal anecdotes are outrageously bleak but in the funniest possible way―and again, Michael Che can’t keep a straight face for long. If you ask us, we don’t get to see Willie nearly enough.

#15: “Weekend Update: David Ortiz's Post-Retirement Plans”


Is anyone better suited to take on pop culture’s larger-than-life personalities than Kenan Thompson? If this send-up of former baseball player David “Big Papi” Ortiz is anything to go by, the answer is no. What makes the character so loveable is that he’s clearly an exaggerated caricature of the actual man, which allows Kenan and the writers to take plenty of creative liberties. Still, while we wouldn’t necessarily get on board with Ortiz’s punny sponsors, a “big lunch” with the sportsman sounds divine. We particularly enjoyed Thomspon’s Ortiz relaying his plans for post-retirement life. Ortiz might be out of the game, but we hope Kenan doesn’t retire this impression soon.

#14: “That's the Game”


In this sketch, Chris Redd’s character decides he wants to takeover over the business and plans a coup to overthrow the boss, played by Thompson. But it quickly becomes clear that he has no idea what running the operation entails, and there’s a reason Thompson’s character was in charge. This sketch is so memorable thanks to Kenan’s typically straight delivery that still garners plenty of laughs. He might be subject to an employee mutiny, but there’s no denying who the king really is. Everyone involved performed the whole sketch excellently, but Thompson and Redd’s dynamic proves they’re an underrated powerhouse team. This sketch was entertaining, and we even learned a little something too.

#13: “Politics Nation: Voter I.D. Disaster”


Ahead of the 2016 elections, Thompson’s Al Sharpton analyzes how new I.D. laws might “disen-frenchfies” black voters. This is arguably one of Kenan’s most spot-on impressions, only made funnier by his consistent mispronunciation of words. The highlight, of course, is when he’s joined by statistical analyst Charles Richards, played by the real Al Sharpton. It’s a testament to Kenan’s talents that he can give such a “phantomnominally” hilarious performance without cracking under pressure to do so in front of the person he’s parodying. It’s unbelievably funny, and we couldn’t stop laughing from beginning to end. Who had Kenan Thompson and Al Sharpton as an iconic comedy duo on their 2016 Bingo cards? Not us!

#12: “Black Panther New Scene”


In this never-seen-before deleted scene, Chris Redd's T'Challa arrives at the mystical realm of Djalia, where he's reunited with his ancestors. During their family reunion, he meets his Uncle M'Butu, who he thought was still alive. M'Butu is delightfully unhinged, and every moment just gets funnier. If the cast could barely keep it together during his reenactment of "The Lion King," what hope did the rest of us have? He even made himself chuckle a little. We're genuinely impressed that anyone made it to the end without corpsing entirely. After watching this sketch, we hoped M'Butu would cameo in the "Black Panther" sequel — even if he's just flipping burgers in the background.

#11: “Them Trumps”


With Alec Baldwin apparently otherwise occupied, “SNL” needed to fill the 45th President-shaped hole in their popular parody line-up. So, Kenan Thompson stepped up to help answer the question: What if the Trumps were black? It’s a satirical take on the man’s infamously offensive standpoints and real-life events but without the white privilege. Thompson does a stellar job at playing Darius Trump, inserting comedy at all the right moments while appearing more dignified than his real-life counterpart. It’s a witty commentary on modern-day America, and with Kenan, at the helm, you simply can’t go wrong. The way he’s able to switch tones so suddenly is remarkable. Any chance we can keep these sketches coming?

#10: “Weekend Update: The Village People on Donald Trump Using Their Music”


During his 2020 campaign, the former president dealt with many cease-and-desists from artists who wanted nothing to do with him. Among those was Victor Willis, better known as the cop from the “Y.M.C.A” music video, who considered legal action after the administration ignored his objections. Apparently, “SNL” thought this was hilarious and translated it into a hysterical Weekend Update bit. Rewriting the lyrics to the 70s classic, Kenan leads the reunited Village People in a spirited performance― albeit with a few additions that could land the group in hot water. The vibrancy and flamboyancy are priceless, and the lyrics are genius. Plus, those pelvic thrusts will live in our heads rent-free for years to come.

#9: “Eternal Spark of Love: Office Romance”


You know who we want to narrate all our meet-cutes? Kenan Thompson. That voice, that piercing gaze, and that indisputable sense of logic. Thompson’s narrator is all for sparks flying, but some quirks are just a little too out there to ignore. In this case, he can’t quite get his head around JLo’s Michelle’s affinity for puppetry. His reactions range from angry to astounded, and occasionally, he’s even rendered silent, relying on crazy eyes to scream his confusion and rage. No matter what, though, this sketch would be nothing without Kenan’s running commentary to keep it afloat. Skits like this are why Kenan Thompson’s often considered one of “SNL’s” finest performers. He gives us everything and more.

#8: “Romance Bookstore”


Even playing the straight character, Kenan manages to steal the show. In this sketch, he runs an erotic bookstore with an employee who takes the job a little too literally. Thompson’s left apologizing to the customers forced to listen to Carol and Dan, sorry Jean-George, play out their fantasies. Still, we're not sure the writers could've given us anything funnier than Kenan's facial expressions as he acts out his frustration. Eventually, the shop owner has enough of the romance duo keeping their customers waiting and goes to confront them ― and that’s when the big twist happens. Who knew that the straight-faced actor in a comedy sketch could be so darn funny? This story deserved a sequel.

#7: “Funeral Service”


In this oddly amusing sketch, musical act Dan and Didi pay respects to their late friend David with a few tracks he apparently penned. It turns out that the deceased kept his musical talents and penchant for “deep club tracks” hidden from his wife. But thanks to an over-the-top series of delightfully inappropriate songs, everyone soon learns about David’s secret hobby. At first, we’re as confused as the other guests, but Dan and Didi’s colorful performances quickly win us over, and, as Leslie Jones says. Arguably funerals, comedy, and “deep club tracks” might not scream comedy gold to you. But in the talented hands of this surprising duo, this sketch is a classic.

#6: “Come Back, Barack”


With a lot of uncertainty up ahead, Kenan collaborated with Chance the Rapper to celebrate the last Christmas with Barack Obama in the White House. The following year, they reunited for another musical performance, this time a soulful ballad about lost love. And who should be the subject of their wistful longing? Yep, the 44th Commander in Chief. The trio reminisces about the good ol’ times, the craziness that ensued since, and even made an eerily spot-on prediction for 2020. Both songs were nominated for an Emmy, with the viral “Come Back Barack” winning for Outstanding Music and Lyrics. We guess the Emmy committee really resonated with these songs. Plus, what a tune!

#5: “Family Feud: Extended Family”


Thompson’s Steve Harvey impression is a classic, and the “Family Feud” sketches never fail to make us laugh. Although apparently, the actual Steve Harvey wasn’t initially a fan and had to grow to appreciate this send-up. These skits have become a highly enjoyable staple on the show, largely thanks to Thompson’s hilarious and fair impression. One of our favorite segments finds the host caught in a family dispute. “SNL’s” Steve Harvey revels in the drama and even fuels it a little much to our enjoyment. This is arguably one of the most unhinged “Family Feud” bits, but Kenan stays on top of the humor and steers the sketch to its hilarious conclusion.

#4: “Sump'n Claus”


Where does Santa get off deciding who’s been naughty and who’s been nice? That’s a little judgmental, don’t you think? Still, if you’re worried you’ve landed on the wrong list, don’t worry; Sump’n Claus has your back. A former North Pole employee, Sump’n Claus, hands out envelopes of cash to anyone in Santa’s bad books. Where does he get all that cash from, we hear you ask? The entire concept is hilarious, and there’s no one better to pull it off than Kenan Thompson. This sketch really showcases his impeccable rhythm, both musically and comically. Is it any wonder this sketch has become a holiday tradition for many fans? Now, if only Sump’n Claus was real…

#3: “Black Jeopardy with Tom Hanks”


“Black Jeopardy” isn’t just one of Kenan’s best gigs as a fictional game show host; it’s become one of the show’s most beloved recurring sketches— and for good reason. It created some of the series’ funniest moments, providing a satirical commentary on society, culture, and politics. Thompson runs the show as Darnell Hayes, a delightfully enthusiastic host who’s often confused by one of the guests on his show. Of course, the best example is the Tom Hanks episode, where the red-voting Doug surprisingly takes to the game like a fish to water. Darnell and Doug share a unique chemistry that keeps us returning to this skit time and time again. It never gets old.

#2: “Diner Lobster”


This sketch started innocently enough with two guys at a diner — what could possibly happen? Even in our wildest imaginations, we couldn't have predicted that it would turn into a full-on "Les Mis" parody with Thompson as a crustacean Jean Valjean. Yet here we are —and it was glorious! From the moment they wheel him out in his water tank, we're already giggling, and by the time he starts singing, we're in stitches. It's hard to believe that it took “SNL” so long to green light this sketch. Perhaps they were just waiting on Kenan to grow into the legendary role. He was claw-some! Hey, Broadway, your next Jean Valjean is treading the boards at Studio 8H.

Before we unveil our top pick, here are a few honorable mentions.

“The Night Before Star Jones' Wedding”
Kenan Plays the Host of “The View” on the Night Before Her Wedding

“Courtroom”
All Rise for This Wisecracking Judge

“Googie Rene's Partially Damaged Halloween Costume Discount Basement”
We Love Googie Rene, but We Think We’ll Take Our Shopping Needs Elsewhere

“Permission”
There’s Nothing Sexier than Consent

#1: “What Up With That?: Samuel L. Jackson & Carrie Brownstein”


If there was any single sketch that cemented Kenan as a national treasure, we’d argue this is it. He plays Diondre Cole, a talk show host who, let’s just say does more singing than talking. Actually, no one really gets to talk, thanks to the host’s overzealous musical tendencies. Anyway, as even the most casual “SNL” viewer knows, one segment from 2012 remains infamously iconic. Guest Samuel L. Jackson dropped a couple of profanities due to what he claimed to be a misunderstanding. Despite this unfortunate curve ball, Kenan seamlessly and professionally brings the skit back on track without breaking character. Thompson doesn’t have nearly enough Emmys for the joy he’s brought for 20 years — to which, we say, “What Up With That?”
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