Saturday Night Live has long been the comedy institution where some of the best comedians of all time are free to get as weird and experimental as they want, week after week. The show’s legacy is built on the stars who’ve passed through Studio 8H, but also on the unforgettable characters they brought to life. These creations became cultural touchstones, the kind of sketches we still quote and rewatch decades later, so it’s only fitting to celebrate the best of them.
Tiny Horse
Animated Character
Timothée Chalamet’s “Tiny Horse” sketches are so random and stupid that they loop back around to being hilarious. In the original, a father and son face losing their farm when Chalamet suddenly breaks into song, tearfully lamenting his tiny horse and realizing he must let it run free. Then, in the surprise sequel, Tiny Horse somehow returns to save the world from the apocalypse. The premise makes no sense whatsoever, and most would never include Tiny Horse on a list, but I’m so impressed with the animated character because I never expected to see the joke work more than once.
Miss Rafferty
Portrayed By Kate McKinnon
Kate McKinnon’s chain-smoking Miss Rafferty has never had a good experience with aliens. In the “Close Encounter” sketches, she joins two fellow abductees who describe their encounters as beautiful and transcendent, while Miss Rafferty’s story spirals out of control. Slouched in her chair, legs spread wide, she recounts her nightmarish experiences with deadpan detail, somehow always ending up pantsless in the process. McKinnon’s mastery of awkward innuendo and her fearless physicality routinely never fail to break her castmates.
Barry and Robin Gibb
Portrayed By Jimmy Fallon And Justin Timberlake
“The Barry Gibb Talk Show” stands as one of Jimmy Fallon’s best SNL sketches, if not the best. Fallon’s over-the-top portrayal of Barry Gibb pairs perfectly with Justin Timberlake’s deadpan take on Gibb’s soft-spoken brother. Not even chest hair or crazy cool medallions can still Barry’s madness, who loses his temper and launches into furious rants at his guests, while Timberlake avoids offering any valuable insight. That ridiculous theme song never leaves your head, either.
Gene Frenkle
Portrayed By Will Ferrell
Considered the stuff of SNL legend, the “More Cowbell” sketch is so iconic that Christopher Walken’s shocking reveal in the SNL 50: Beyond Saturday Night documentary was that it ruined his life. The entire bit hinges on two performers: Christopher Walken as eccentric producer Bruce Dickinson, and Gene Will Ferrell as the overly enthusiastic cowbell player, Gene Frenkle.
Ferrell’s unexpected choice to walk out in an absurdly tight shirt that exposes his hairy belly button caught everyone off guard, pushing the cast, especially Jimmy Fallon, to break mid-sketch: except, of course, Chris “the Iceman” Parnell. But for once, no one could blame Fallon.
The Spartan Cheerleaders
Portrayed By Will Ferrell And Cheri Oteri
The “Spartan Cheerleaders” sketches were so popular in the late 1990s that SNL ended up producing an incredible 17 of them, all centered on Will Ferrell’s Craig and Cheri Oteri’s Arianna. The two overly enthusiastic cheerleaders never actually made the squad, so they brought their relentless energy to the most mundane sporting events imaginable, from chess matches to bowling tournaments.
Their complete obliviousness to how out of place they are is what makes them so endearing. Ferrell and Oteri’s chemistry, rapid-fire banter, and even their hilarious height difference create a perfect mix of awkward charm and pure commitment, making “Spartan Cheerleaders” one of the best recurring SNL sketches of the 1990s.
Diondre Cole
Portrayed By Kenan Thompson
Anchored by Kenan Thompson’s smooth-talking host Diondre Cole, “What Up With That?” promises thoughtful interviews but quickly devolves into nonstop singing and dancing. Each time, Cole cuts off his guests mid-sentence and never gives poor Bill Hader’s Lindsey Buckingham the chance to speak, despite swearing he’ll get his turn “next time.”
But Diondre has everything that justifies Kenan Thompson’s endurance as the longest-running SNL cast member: mischievous grins, one-liner shouts, close-up reactions, and a presence that demands complete attention. Between Thompson’s infectious charisma and Jason Sudeikis’s iconic red jumpsuit running man tearing up the stage, I have no idea how the two never collapsed from exhaustion by the end of it.
Shy Ronnie
Portrayed By Andy Samberg
Shy Ronnie had two chances to impress Rihanna and he squandered them both. A painfully awkward rapper who freezes up in front of others but secretly has real talent when no one’s watching is completely Andy Samberg-coded. In two of The Lonely Island’s best SNL Digital Shorts, the Shy Ronnie music videos perfectly balance cringe and charm, with Rihanna’s deadpan reactions amplifying the absurdity of Ronnie’s timid attempts to perform. Hopefully one day Andy Samberg and Rihanna will return to complete the “Shy Ronnie” trilogy.
Gilly
Portrayed By Kristen Wiig
Kristen Wiig has no shortage of cringe-inducing characters that make you laugh and squirm, and Gilly is up there as one of her best. Gilly is a prankster who disrupts situations with more and more sadistic pranks as the sketch goes on. Everything from Wiig’s bubbly-haired costume design to her creepy smile, childish dance moves, and one-line “Sorry!”s make this recurring SNL character so funny, and it definitely helps that she has Will Forte’s stern adult presence to bounce off of.
Harry Caray
Portrayed By Will Ferrell
I have no idea who the real Cubs announcer was (I had to Google it), but Will Ferrell’s version of Harry Caray is so bizarrely magnetic that it doesn’t matter. With his scrunched face behind oversized glasses and a voice that seems permanently stuck at max, he blurts out wild, obvious observations that derail every conversation. The absurdity of his delivery, combined with the confusion and discomfort of his guests, makes for some of the funniest moments on SNL.
Herb Welch
Portrayed By Bill Hader
Bill Hader definitely channels his inner Clint Eastwood for Herb Welch, the cranky, aging newscaster who’s had enough of “beatnik” young people. Hader nails the archetype of the out-of-touch old man, fumbling his way through live broadcasts with incompetence. Whether he’s speaking too close to the mic, responding to questions with misplaced aggression, or physically whacking the microphone into interviewees’ faces, Hader’s Herb Welch is totally unhinged.
