If you’re familiar with the entirety of his career, it’s no surprise that after working on the show for 20 years (at the time of writing) Kenan Thompson is the longest-serving cast member in Saturday Night Live history. Audience members who came of age in the 90s likely remember him as one of the breakout stars of the Nickelodeon sketch comedy show All That. Both he and fellow cast member Kel Mitchell were so successful and popular on the show that they transitioned into their own sitcom, appropriately titled Kenan and Kel (the comedy duo reunited on the Keke Palmer-hosted episode of SNL). In those early years, Thompson demonstrated a keen ability to deliver any line in such a way that it will get a laugh, even if it was something mundane.
During his two decades on the venerable comedy series, Thompson has remained a valuable utility player. Some people hit it big on the show with larger-than-life characters that strike a chord with the pop culture zeitgeist, while others stick to the sidelines deftly setting up jokes for others to pay off. Thompson does everything. If you need a straight man to play off of a zanier character, he’s got you covered. If you need a big, loud, and delusional character who barely makes sense, he’ll excel there too. There’s really nothing he can’t do and to honor his shocking versatility, we’re ranking Thompson's most iconic characters on SNL.
7 Reese De’What
As the host of a recurring segment called Cinema Classics, the character of Reese De’What isn’t even the focus of the sketches themselves. His role is to introduce a movie, provide some context, and give us little insights into his personal life. The bulk of each sketch is primarily dedicated to Kate McKinnon doing impressions of classic Hollywood stars in increasingly ridiculous situations. Despite that, Thompson manages to steal the show by playing Reese with a kind of confused enthusiasm. He’s excited about what he’s talking about, but doesn’t seem to understand why he’s the one there introducing these clips. Had any other actor taken that role, it could have come across as dry and dull, but with his quick line delivery and changing tone of voice (the way he says his name alone is hysterical), Thompson makes the character memorable.
6 Lorenzo McIntosh
The concept behind the Scared Straight sketches is that young people who have been brought into the police station on relatively minor offenses that could possibly lead to more extreme crimes in the future are scared into behaving themselves after meeting with an inmate named Lorenzo McIntosh, played by Thompson. Lorenzo is a hardened criminal with a history of crime that includes stealing cookies, hats, newspapers, baby food, hats, newspapers, and hats. The joke is that he’s obviously a nobody pretending to be tough and Kenan delivers every single line with an unexpected cadence that makes you laugh at everything he says. As the sketches continued, Lorenzo became a more supporting character, allowing the hosts to shine by allowing them to out-crazy him. The most popular example is probably the late Betty White messing with Bill Hader, but Thompson is the anchor that holds the central concept in place. Without him, these sketches never would have continued.
5 Diner Lobster
The skit in which Pete Davidson orders lobster at a diner is so surreal and unexpected that you would be forgiven for taking in the entire experience rather than focusing on Thompson’s performance as the eponymous lobster. However, if the sketch were just weird, it probably wouldn’t have had such a lasting impression since its premiere. What sells the concept is the commitment of its cast, and Thompson sets the tone. Dressed in a ridiculous outfit, the Diner Lobster is wheeled out from a back room in a tank that’s too small for him. Thompson lifts his head, blinks as if just being awakened, takes a moment, and then lets out the perfectly-timed first line of his song. He plays it with all the gravitas of a trained stage performer who refuses to believe that their character makes no sense and that they look ridiculous. He appears so committed to the role that everyone else around him is forced to bring the same energy, resulting in an SNL sketch for the record books.
4 Bill Cosby
For whatever reason, when it comes to celebrity impressions, Thompson doesn’t get nearly the respect he deserves. Sure, there have been plenty of great impressionists in the history of the show (Dana Carvey and Darrell Hammond are obvious examples), but few of his impressions have had the same staying power as others. That being said, it can be difficult to decide which impression to highlight, but because of the sheer bravery it took to mock the man for his horrific actions after already working with him (Thompson was in the Fat Albert movie), it has to be Bill Cosby. Most actors nail their Cosby impressions by simply straining their voices, rolling their eyes, and moving their heads around to accentuate what they’re saying. Thompson is no different, but there’s a twinkle in his eye almost as if he’s getting away with something. Every time he pauses for a laugh, it looks like he is trying not to laugh at the absurdity of his performance which makes the audience feel like they’re in on the joke.
3 Darnell Hayes
Game show parodies are a Saturday Night Live staple because all they require is a group of funny characters saying funny things in response to questions. For years, Celebrity Jeopardy brought the house down with Will Ferrell’s frustrated Alex Trebek struggling to keep it together while these seemingly mindless celebrities (especially Sean Connery) refuse to pay attention. Instead of trying to recreate the magic of those sketches, SNL created Black Jeopardy, where contestants answer questions that only members of the Black community should know the answers to. The host is Darnell Hayes and, again, Thompson takes a character who could easily just stand there and deliver lines with no effort and turns him into a compelling personality. For an exceptional example, watch the hesitation with which he allows himself to be impressed by the similarities he shares with a MAGA-loving white man played by Tom Hanks (via YouTube). We get just a smidgeon of vulnerability there and Thompson sells it perfectly.
2 Steve Harvey
Another exceptional game show parody also features another exceptional impression by Thompson: Steve Harvey as the host of Family Feud. Harvey isn’t the easiest host of the long-running game show since he doesn’t have many quirks to latch onto, but Thompson milks what’s there for all its worth. His mustache is obnoxiously big, and it threatens to dwarf the wide grin beneath it. His eyes are almost constantly on the verge of falling out of their sockets, and he has a real affinity for calling people “player.” Is it a totally accurate impression? No, but it doesn’t have to be. It gets to the silly core of Harvey and plays everything to a cartoonish degree, not unlike the majority of Dana Carvey’s impressions.
1 Diondre Cole
It’s virtually impossible not to love What Up With That? Despite the fact that every installment has the same exact structure, the specifics are so wildly different that it keeps surprising you. It usually goes like this: Diondre comes out dancing and singing the theme song to his show before introducing his guests which usually consist of two celebrities (played by themselves) and lead guitarist of Fleetwood Mac Lindsey Buckingham played by Bill Hader. As Diondre begins to interview the first guest, something they say triggers his need to sing and dance, and he goes back into the theme song. As he sings, he introduces bizarre guests who join him onstage. What keeps everything fresh is the fact that we never know just how strange the guests are going to be. Besides, Diondre’s enthusiasm is infectious, and you can tell Thompson has an absolute blast playing the character.