10 of Adam Sandler’s Best Saturday Night Live Sketches

Adam Sandler on SNL. Photo: NBC

Since Adam Sandler was fired from (and quit) Saturday Night Live after only five years on the show, he hasn’t exactly been haunting the halls in 8H. He’s made a couple of appearances, but for the most part, nah. When asked about the possibility of hosting SNL on Norm Macdonald Live just a few years ago, Sandler said, “Why should I? I don’t know how good it would be.” He added, “I’m slow now. There are guys who love doing it who are great at doing it — I just don’t know how good I’d be doing it, and I did what I could do on that show.” Sandler is set to make his SNL hosting debut this weekend, so presumably Lorne Michaels managed to convince him otherwise.

In honor of his return, we rounded up ten of Sandler’s best sketches while he was an SNL cast member. Those who found Sandler anytime after Billy Madison may not know some of these bits, but there won’t be surprises on this list for longtime Sandler fans. His biggest boosters have remained steadfast since the ’90s — and, if they’re old enough, may have a DVD copy of Saturday Night Live: The Best of Adam Sandler sitting in a box somewhere. Now, about 25 years after his SNL days, Sandler’s best bits have been pretty well canonized; there aren’t many obscure favorites capturing fans’ imagination, and if anything, some of the classics have lost their luster — “Canteen Boy,” for example, hasn’t exactly aged well. Still, there’s plenty of reminders why Sandler is a king of the straightforward and sophomoric bit.

Bobby Watches Grandma

Ever wanted to see Michael Keaton beat up Chris Farley while Sandler looks on in old-lady drag? This sketch will scratch that itch. While the favored grandchild, Joey (Keaton), gets busy in a back room, he asks Bobby (Farley) to keep their grandmother (Sandler) busy. The old lady gripes, wails, and blames poor Bobby for everything; Bobby breaks things and gets whacked in the head by his brother. More importantly, the sketch plays on what is essentially Sandler’s Madea, a loud and fussy grandma who made appearances in his early stand-up and carries on in later projects. And there are options for watching this one: either on air or at dress, the sketch became entirely about Farley losing his wig and all the actors breaking.

The Denise Show: Five Weeks After

This is a crystal-clear idea that not only puts Sandler center stage but forces him to do a tiny bit of acting, too. It’s a talk show hosted by a heartbroken guy called Brian, who sits on his couch with photographic evidence of his relationship with former girlfriend Denise. Five weeks after the breakup, he’s obsessed with her whereabouts, the company she keeps, and why-oh-why she won’t just come back to him. This show is a journey through his anger and sadness posing as a talk show. Morose and defeated though he may be, Sandler plays a juvenile version of a morose adult that certainly touches on Sandler’s other mode of being (as seen in Punch Drunk Love and The Meyerowitz Stories).

Bruce Springsteen on Thanksgiving

Sandler is happiest (and most successful) playing some version of the man-boy, and he was never a big impressionist. Look past the Bonos and Axl Roses, however, and his Bruce Springsteen is a clear winner. He once annoyed Courtney Cox onstage with his rendition of “Dancin’ in the Dark,” but this early version of “The Thanksgiving Song” injects a little more Adam into its Bruuuce. The lyrics hit some of that hardscrabble Jersey imagery while tossing a few other ideas in Springsteen’s mouth (“Eat that turkey off a table or off your lap / My favorite guy on WKRP is Venus Flytrap”). And Sandler’s impression has the requisite scowls and growls and wails to make it work.

High-School Liars’ Club

Photo: NBC

While Sandler has to share the spotlight here, it’s a great ensemble piece that holds up a lot better than the Gap Girls. Three high-school kids compete in this game show about who can tell the best whoppers about beer drinking, partying with Van Halen, and how much their older brother can bench-press. Sandler pays a hapless boob who can’t lie to save his life but sure is going to try. Hearing him blabber about a sister who is in “the Olympic SWAT team up in Canada” never gets old. The writing and all the performances are great, maybe sweeter and sadder now that Phil Hartman, Chris Farley, and Luke Perry aren’t around. (The clip isn’t embeddable, but you can watch it on the NBC website.)

Zagat’s With Hank and Beverly Gelfand

Another example of the Farley-Sandler connection, and another sketch in which Sandler is happy to lend a stoic counterpoint to his big, boisterous pal. The husband-and-wife team of Hank and Beverly try to plan a dinner outing. Mostly, Bev (Farley) reads from a Zagat’s restaurant guide about outdoor gardens and zesty meat sauces while Hank (Sandler) pleads for the sweet mercy of death. The premise is accessible for anyone who’s been part of a couple, and the rest is the play between these two friends. Farley’s take on Bev, who is tickled by every new potential restaurant experience, wouldn’t be nearly as funny as it is without Sandler’s grousing — and, clearly recognizable just beneath, his great appreciation for Farley.

Halloween Costume Ideas

It doesn’t get simpler than Sandler screwing up his face and saying, “I’m Smiley Boy, gimmee some candy!” The idea here is Sandler offering up tips about how to stretch a dollar when it comes to creating a Halloween costume. Over the course of three appearances on “Weekend Update,” Sandler hides his arms in his shirt, ducks under the “Update” desk, puts tea bags between his teeth, and covers his face with newspapers; he then announces how crazy his predicament is and begs over and over again for candy. It’s silly and it’s ingratiating; this is not a character, it’s Sandler at his most elemental.

The Herlihy Boy House-Sitting Service

Sandler’s character Tim Herlihy, named after the longtime Sandler collaborator and onetime SNL writer, directly addresses the camera and pathetically pleads with some unnamed homeowner to let him house-sit. After presenting Tim’s earnest pleas to water plants and bring in mail, the camera reveals Farley, some supportive elder in a cardigan, losing his shit because the reluctant homeowner won’t let this kid take care of things. As with all other Sandler-Farley sketches, it’s really the back-and-forth between these two that sells it. (And playing the straight man to Farley, or just being onstage with Farley, means it’s ultimately Farley’s show.) It’s the sketch version of that soft-loud-soft-loud structure in ’90s-era rock.

Schmidt’s Gay

Two guys (Sandler and Farley) house-sit some dumpy bungalow where even the pool has no water. But with a little magic, and a bottle of Schmidt’s Gay beer, the place is transformed into a tropical paradise. The pool fills with beautiful water and the water fills with beautiful dudes — and these dudes are ready to party. Sandler and Farley play it without winking, so there’s no gay panic; it’s just two dudes thrilled to see some banana hammocks and hear beefcakes invite them to “get wet.” It might help to revisit a few beer commercials from the ’90s, but anyone who has sucked up enough advertising will appreciate the way in which this spoof flips heteronormative gawking on its head.

Opera Man

Sandler’s best-remembered SNL character is, at heart, an excuse to joyfully snipe at the news of the day. In cape and long black wig, Sandler sings snatches of famous operatic solos while taking playful jabs at celebrities and politicians in mock Italian. (The uninitiated and curious will probably want to Google headlines from, say, ’92 to ’95 to make the most of it.) Some of the broader swipes wouldn’t cut it today, but the best Opera Man moments bring out one of the things Sandler does well: summing up big ideas with one distilled, brilliantly goofy response. Cajun Man isn’t on this list, but he fits into this same category — character and conceit stripped down to just a syllable or two.

The Hanukkah Song

Truth be told, this list could probably be half, if not more, Sandler songs. (See another musical Sandler classic, “Lunch Lady Land.”) But anyone who knows this one knows the biggies and knows how they work: Sandler writes a paean to a neglected holiday — full of cute rhymes, non sequiturs, and nonsense phrases — and delivers it like a mischievous 8-year-old. And to prove God is in the details, these songs home in on favorite aspects of the holidays rather than try to cover all the bases. For V-Day, Sandler espoused love for his red hooded sweatshirt; for Thanksgiving, he talked turkey. To help flesh out the Hanukkah songbook, Sandler considers every Jewish celebrity or even Jewish celebrity who might be enjoying the Festival of Lights. Best enjoyed with a “gin-and-tonikah.”

10 of Adam Sandler’s Best Saturday Night Live Sketches