Every Adam Sandler Character from SNL, Ranked

The SportsAlcohol.com editorial core closely follows Saturday Night Live, and perhaps not coincidentally also closely follows the career of Adam Sandler, through a series of numerous lows and occasional highs. So obviously some of our most misguided interests were piqued when it was announced that the Sandman was down for his first-ever Saturday Night Live hosting gig, airing this Saturday, May 4th, on the good old NBC television network. Sandler has returned to the show for a few celebrations and one show-opening musical number, but he’s demurred on the possibility of hosting for many years. Though he currently alternates Netflix movies with the occasional arthouse indie picture (!), Sandler is still a major star, and his return to the show where he spent an uneven five years as a writer and performer qualifies to us as a major pop-culture event. So we decided to figure out a complete ranking of Sandler’s (non-impression) recurring characters from his SNL years.

As it turns out, there aren’t really that many; one of these 16 “characters” doesn’t really qualify, and 6 of the remaining 15 are Weekend Update bits. Really, Sandler’s signature character was, well, Adam Sandler: the guitar-playing or Halloween-costume-suggesting goofball who showed up at the Update desk to goad Kevin Nealon into singing or to make faces at Norm MacDonald and/or Chris Farley. Sandler is not a virtuosic sketch performer; his stand-up comedy roots show, and it’s arguable that the stand-up-bro sensibility of so many mid-90s cast members is what led to one of the program’s worst slumps. But Sandler and his guys — Chris Farley, David Spade, to a much lesser extent Rob Schneider — all had great moments on the show.

To rank these characters,, I sent a master list to a bunch of people who I thought might know or care enough about Adam Sandler to send back ranked ballots. Only I, Nathaniel, and SNL fan Brian had enough of an opinion to weigh in. And, as it turns out, our ballots were often pretty much in sync, making this an unusually strong consensus in terms of what goes where. The Sandman: the great uniter…of people who watched him on SNL when they were younger.

Every Adam Sandler Character from SNL, Ranked

16. Two Guys from a Religious Cult

To be honest, I forgot to include this on my initial master list, because I forgot that it was something Sandler and David Spade did multiple times, so it didn’t really have a chance to shine in the voting process. But this also isn’t really as funny as it should be, and didn’t really bear repeating multiple times.

15. Various Restaurant Guys

This is kind of a cheat; technically, the overly affectionate Italian waiters are not the same characters as the gyro-shop workers who incessantly ask, “you like-a da juice?” The latter is arguably even a parody of the repetitive format of the former, and even has a delightful meta ending where David Spade walks into the gyro shop and requests that the sketch end. But Sandler playing an accented, weirdly insinuating food-service worker feels like a recurring thing even if it’s not. It’s only ranked this low because (besides not being a proper character), it’s more of an ensemble deal.

14. Sleepyhead

He dozes at the Weekend Update desk and mutters dreamlike nonsense until finally arriving at current-events commentary. That’s the bit. It’s the comedy equivalent of the cheap Halloween costumes Sandler pitches in a series of much funnier Weekend Update segments. Sandler wearing an old-timey stocking hat, though, is good for a laugh.

13. Angelo from Good Morning Brooklyn

Given the Sandman’s Brooklyn roots, it’s a little weird in retrospect that this was a Jay Mohr sketch where Sandler had a recurring role as a particularly quarrelsome guy from The Neighborhood, a correspond whose chief concerns were yelling at offscreen figures and administering beatings. OK, maybe not that weird.

12. Frank Dippy

Sandler is probably best known for his Weekend Update songs performed as himself and/or Opera Man, but he had a lot of one-joke Update characters, too, like this double act with Chris Farley (playing Hank Doodle), a couple of supposedly regular guys offering issue commentary that—get this this—never arrives at an actual point! To this bit’s credit, it’s a lot more succinct than, say, Fred Armisen’s Nicholas Fehn character, which did basically the same thing at greater length, years later. And Sandler is undoubtedly skilled at doddering through half-finished sentences, just as Farley can affect a vaguely Midwestern accent and get stuck in a loop of “so I sez to the guy, I sez” with aplomb. Plenty of Sandler and/or Farley and/or Spade bits are pretty simple; this one just doesn’t have enough weirdness to distinguish it.

11. Tony Vallencourt

Here Sandler again gets ahead of the curve: before Jimmy Fallon and Rachel Dratch did their “Boston Teens” bit, he was a vulgar Bostonian and Celtics fan. This isn’t one of his best-known characters, but Tony (who appeared on a New England game show called “What’s the Best Way?”) did once get his show-opening sketch, during a time when the cold open wasn’t reserved exclusively for wan political bits. It was also a time when the show was struggling mightily to retain any kind of audience affection, which probably explains why a third-tier Sandler character got to do a solo direct-address sketch at the top of the broadcast. Still, in Sandler’s catalog of violent numbskulls, Tony Vallencourt has some regional specificity. Fans will also note that Tony’s surname was reused for Fairuza Balk character in The Waterboy, and Sandler revived his mush-mouthed Boston accent for the ill-regarded That’s My Boy.

10. Lucy, of the Gap Girls

I have a lot of affection for the Gap Girls, because it’s super-90s, shows off plenty of Sandler/Farley/Spade chemistry, and I’m a sucker for Valley Girl affectations. On the negative side, a lot of it plays as kind of condescending today; there are plenty of sketch performers who imbue their drag characters with a lot of genuine human feeling, and those sketch performers are not so much SNL’s mid-90s frat pack. To be honest, Sandler’s Lucy is probably the least convincing of the three main Gap Girls, as Spade is more in touch with his inner bitchy teenager and Farley’s hapless Chrissy feels like a natural extension of his persona.

9. Cajun Man

In retrospect, it’s kind of amazing (or, I guess, a-maze-on) how little of Cajun Man Sandler revived for The Waterboy.

8. Audience McGee

My Sandler ballot had this one way up high, because I’m a sucker for characters who don’t really have their own sketches, instead materializing at odd moments as needed—in this case, typically for Q&A or other audience-based interruptions. My strongest memory of this character as it aired was his interruption of a Pat sketch with Julia Sweeney and Harvey Keitel, at a crucial juncture when Pat is asked point-blank whether they are a man or a woman. Setting aside both the tedium and misguided nature of this sketch now, I always smile thinking of Sandler’s high-pitched voice urgently explaining that the ambiguity of Pat is part of the fun. All-time best Pat sketch, to be honest.

7. Canteen Boy

These days, Canteen Boy is probably best-known for the notorious sketch where his scoutmaster, played by Alec Baldwin, attempts to seduce him during a camping trip. But that was just one of six sketches where Canteen Boy appeared in a single season (perhaps owing to the controversy, he appeared just once in Sandler’s following and final season, during a monologue bit where returning host Baldwin attempts to sanitize the scout leader sketch). His real legacy is the clear inspiration for Sandler’s wildly popular Bobby Boucher character in The Waterboy, which is basically 80% Canteen Boy and 20% Cajun Man. In retrospect, it makes sense that this variation on the character resonated; Sandler’s funny voices and affectations may seem broad, but sometimes, as with Canteen Boy, he feels like he’s really digging into a character’s bizarre psychology. Also sometimes forgotten between the controversies and the Waterboy popularity: Canteen Boy had the power to summon snakes!

6. Opera Man

I’m guessing Adam Sandler has never watched a real opera. I haven’t either, which probably helps to explain why I think this mostly-Update bit is so much fun.

5. Brian, from The Denise Show

One of Sandler’s more grounded and best-observed bits, as well as one of show’s better “mundane idea becomes a talk show for some reason” sketches, this early portrayal of self-pitying male rage has teenager Brian hosting a stalker-ish talk show scrutinizing the details of, and emotional fallout from, his break-up with Denise (Shannen Doherty, who appeared in the first sketch in person, and in subsequent sketches via a framed photograph). I hope they revive it when Sandler hosts, although it won’t be quite the same without Phil Hartman calling in as Brian’s irritated father.

4. Hank Gelfand

I don’t think Adam Sandler has as big a reputation as a serial laugher as fellow SNL alums Jimmy Fallon and Horatio Sanz. Even though he and Andy Samberg chronicled the rich history of SNL crack-ups (with plenty of shout-outs to Fallon and Sanz), there aren’t as many replayed clips of the Sandman losing it as completely as, say, Bill Hader playing Stefon. (Or in other sketches! As he grew more comfortable on the show, Hader also became more prone to in-sketch giggling.) Maybe that’s because a lot of folks probably picture Sandler’s default expression as a kind of barely contained smirk; in a lot of his bits, he seems just on the verge of breaking, but doesn’t quite do it, or works a half-laugh into the actual character (since many of his characters are basically Adam Sandler with a guitar, or Adam Sandler with a little more social anxiety). When Sandler actually loses it, though, is when he’s face to face with Chris Farley—admittedly, seemingly a common affliction among Farley’s castmates. Maybe because Farley isn’t around anymore, there’s something oddly sweet about how he can clearly make Sandler lose it just by, say, making a silly face or touching his knee—to the point where even an amusingly mean-spirited sketch about an elderly couple where the husband wishes death upon himself as his wife enthusiastically reads from the Zagat’s restaurant guide winds up seeming kind of affectionate anyway. Hank and Beverly Gelfand may not be equally content in their marriage (seriously, Hank asks for cancer and attempts suicide multiple times), but Farley and Sandler certainly had old-married-couple chemistry.

3. Gil Graham

Adam Sandler thinks violence is funny. Lots of people do, of course, but given that he’s a professional comedian with experience in stand-up, sketch comedy, and tons of movies, it feels notable that Sandler seems fascinated with the mechanics and circumstances of merciless beatings and/or attacks. Lots of his movies feature slapstick predicated on brutal beatings, but in a lot of ways, there’s something purer about Sandler simply describing those beatings with enthusiastic detail. His rock correspondent/fanboy Gil Graham, forever rocking a Led Zeppelin t-shirt, glasses, and a raspy voice that Sandler would later repurpose in Little Nicky, describes his concert experiences, which inevitably feature various unseen characters bullying him, beating him up, or otherwise punishing him, seemingly at random, for the crime of being an enthusiastic rock geek (one of his least harrowing experiences involves two teenage girls offering him $2,000 for his concert tickets and absconding without paying him). The fact that Graham comes on Weekend Update to tell the tales of his abject humiliation, and continues attending rock shows even though he experiences them principally from dumpsters or portable restrooms, gives him a kind of strange dignity.

2. Pedro, of Captain Jim and Pedro

This basically Sandler’s “buffoon” voice from his early comedy albums made flesh, but the sketch’s premise is so delightful that it doesn’t come across as lazy. Captain Jim (Tim Meadows) and Pedro (Adam Sandler) are sailors and friends who were marooned on a desert island for years before getting rescued and reintegrating into normal society. Their two sketches find them applying for a job at Foot Locker, and going on a double date. Captain Jim speaks of their experiences with cheerful plain-spokenness; Pedro utters nonsense anecdotes about his deathless rivalry with island monkeys. Both of them, for reasons so unexplained that it still makes me laugh to think about it, continue to wear the tattered clothes they clearly kept for their entire stranding.

1. The Herlihy Boy

For the love all that’s holy, just let the boy appear on your sketch comedy series.