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This weekend marks the season premiere of Saturday Night Live, which is headed into its 40th season. In honor of this landmark anniversary, the Decider team has been engaged in furious debates about the merits of various original characters that the Not Ready For Primetime players have performed on the show over the years. Throughout the course of this week, we’ll be counting down our list of the TOP 40 SNL CHARACTERS OF ALL-TIME (which, we should note, does NOT include impressions).

The schedule is as follows:
Tuesday, September 23: #40-31
Wednesday, September 24: #30-21
Today: #20-11
Friday, September 26: The Top Ten

Now, without further ado…

20. DICK IN A BOX GUYS

STARRING: Andy Samberg and Justin Timberlake
APPEARANCES: 6 (2006-2013)
WHY: We’ve got all the respect in the world for “Lazy Sunday,” but “Dick In A Box” will always be The Lonely Island’s most influential SNL moment. This sketch first aired back in December of 2006, back when Twitter was still in its nascent stages, but it caused Godzilla-sized tsunamis throughout pop culture as soon as it aired. Samberg & Timberlake’s turn as Color Me Badd-esque R&B douchefuses—yes, that’s douche + doofus—worked because it somehow managed to play to both their strengths AND weaknesses (their likability and cheesiness, respectively). The demand for these characters was so great that they revisited these nameless characters FIVE other times post “D In a B,” including the musical numbers “Motherlover” and “3-Way (The Golden Rule).”

19. BILL BRASKY

STARRING: Will Ferrell, David Koechner, Mark McKinney, Alec Baldwin, Tim Meadows
APPEARANCES: 6 (1996-2013)
WHY: 10 years before the super popular “Chuck Norris Facts” meme began running wild, there was Bill Brasky. The first appearance of the drunk salesmen who worked to outdrink and out-boast themselves with ribald tales of their encounters with a near-mythical figure named Bill Brasky came during an Alec Baldwin-hosted episode back in January of 1996 in the classic “last sketch of the night” slot, a position it would maintain for each of the six times the sketch aired. Watch the original sketch above, but only if you’re comfortable laughing out loud at the office.

18. TARGET LADY

STARRING: Kristin Wiig
APPEARANCES: 10 (2005-13)
WHY: “APPROVED!” Wiig’s Groundlings training was perhaps best realized in this recurring sketch where she portrayed, yes, a Target employee. Laying a Midwestern accent on THICK, Wiig perfectly embodied the kind of mind-blowing, misplaced optimism that one sometimes encounters at big box stores in the heartland. This regional-specificity allowed Wiig connect in what the Coastal elites dismissingly refer to as the flyover states, and her ability to infuse Target Lady with equal parts sweetness and strangeness made for a truly memorable character.

17. BILL SWERSKI’S SUPER FANS

STARRING: Robert Smigel, George Wendt, Chris Farley, Mike Myers
APPEARANCES: 10 (1991-2003)
WHY: DA BEARS! DA BULLS! Speaking of Midwestern jokes, the Chicago accents of the Super Fans were even thicker than the characters mustaches. Comedic genius/SNL writer Robert Smigel based this sketch on the real life Chicagoland sports talk TV show The Sportswriters, a precursor to ESPN’s long-running Sports Reporters franchise, and the sketch became SO popular that it was recently resurrected some 22 years after its debut for a popular series of State Farm commercials. DITKA!

16. ARIANNA AND CRAIG, THE SPARTAN CHEERLEADERS

STARRING: Will Ferrell and Cheri Oteri
APPEARANCES: 17 (1991-1995)
WHY: Betcha didn’t know that this sketch was born from the mind of … Chris Kattan? Yes, it’s true, the Spartan Cheerleaders were the brain~~child~~children of Mango himself, but don’t hold that against them! Arianna and Craig were not the greatest cheerleaders in the history of the sport, which is why they typically turned up at events like chess matches and swim meets. However, what they lacked in athletic ability they more than made up for in lovability. The friendship between these two was unflappable, no matter the circumstances. Haters gonna hate, but the Spartan Cheerleaders always just shook it off.

15. MACGRUBER

STARRING: Will Forte
APPEARANCES: 9 (2007-10)
WHY: One part MacGyver and one part Toonces, MacGruber is THE most ludicrously hilarious—with one exception that we’ll discuss tomorrow—character of the last 10 years of SNL. What seemed like a one laugh kind of joke—inept spy dies in a fiery explosion because of his ineptitude—instead went off in some SERIOUSLY weird and subversive directions. For instance, take the series of bits above, in which MacGruber starts feeling self-conscious about his age and considering his options (“he might go get some work done”). Things get CONSIDERABLY weirder from there (“microderm abrasion and a buttload of hairplugs”), which is why we will always have a place in our hearts for Grubes.

14. THE CONTINENTAL

STARRING: Christopher Walken
APPEARANCES: 6 (1990-2003)
WHY: Chris Walken is a legend … and a legendary weirdo. He’s one of the best guest hosts in SNL history, and The Continental will always be his standout character. In this recurring series of sketches, Walken plays a character that is probably best described as a Eurotrash Hugh Hefner, someone who lures a series of young women into his shabbily luxurious New York City apartment under false pretenses and then tries to bed them. It’s an unsettling set-up, for sure, which is why it’s so brilliant. Walken oozes both old world charm and new world desperation in equal measure, and we sincerely hope that we can see the 71-year-old Walken appear as host sometime during this 40th season so we can give The Continental the proper goodbye send-off it so richly deserves.

13. BRIAN FELLOW

STARRING: Tracy Morgan
APPEARANCES: 12 (1999-2009)
WHY: Before he found his footing as the host of Safari Planet, Tracy Morgan debuted his Brian Fellow character on Weekend Update where he played … a sports reporter who accused everyone of being gay? It’s true! This bit did NOT go over so well, but credit Lorne Michaels for realizing this character’s potential. They took four months to polish the character behind the scenes, and the result was Brian Fellow’s Safari Planet. They swapped his propensity for outing athletes with an air of dunderheaded cluelessness about the animal kingdom, a recipe that worked wonders. I’M BRIAN FELLOW!

12. HANS AND FRANS

STARRING: Dana Carvey and Kevin Nealon
APPEARANCES: 20 (1987-99)
WHY: “We are here to pump …[clap]… YOU UP!” Arnold Schwarzenegger was the biggest star in the world when Dana Carvey and Kevin Nealon debuted their Hans & Franz characters back in 1987, and their quest to rid the world of “girlie men” instantly gripped the nation. If you were alive at the time when these sketches first aired, you’ll recall that there wasn’t a man, woman, or child alive who didn’t do their own take on their “pump you up” catchphrase. These two beloved fitness professionals created such an impact that they, much like the Bill Swerski superfans, are now appearing in commercials almost 30 years after they first debuted on the show.

11. LINDA RICHMAN

STARRING: Mike Myers
APPEARANCES: 15 (1991-97)
WHY: One of the many testaments to the comedic genius of Mike Myers is that he, a Canadian man, was able to so convincingly take on the role of a Jewish woman in the series of sketches originally known as “Coffee Talk With Paul Berman.” The premise at play was that Berman was out sick after developing shpilkis in his genechtagazoink, and the only sorta qualified Richman was called in to substitute as host. Her catchphrases—”Like buttah”, “Verklempt” and “Discuss”—all became signature lines, and Richman’s/Myers’ influence grew to such a point that they were able to get Madonna, Roseanne Barr, and Barbra Streisand (!!!) to all appear in the same sketch together (see above).

Join us tomorrow, when we’ll be counting down the Top 10 of the TOP 40 SNL CHARACTERS OF ALL-TIME!

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