On air since 1975, Saturday Night Live has earned its place as one of television’s longest‑running comedy powerhouses. Across its 48 seasons, the show’s most enduring and beloved recurring segment is the Weekend Update, where one or two anchors deliver quick‑fire news headlines topped with razor‑sharp jokes. The format is a guaranteed laugh‑generator, blending snappy commentary with topical relevance, and the 10 best snl moments showcase why it remains a cultural touchstone.

10 best snl: The Ultimate Countdown

10. Adam Sandler on Hanukkah

Our first entry hurls us back to the mid‑1990s, when Norm Macdonald still helmed the desk. In this clip, Adam Sandler opens up about feeling like the odd Jewish kid amid a sea of Christmas carols, lamenting the scarcity of Hanukkah tunes.

In response, he pens a catchy Hanukkah anthem that rattles off a roster of famous faces whose Jewish roots aren’t widely recognized. It’s a goofy, feel‑good jam that surely lifted the spirits of any kid who’d ever felt left out.

We love his clever rhymes—think “Scrooge is” paired with “Stooges”—and, of course, the sheer joy of hearing Sandler break into song.

9. Will Smith and Chris Rock Slap Attack

Sliding into ninth place is the most timely of the lot—a rapid‑fire recap of the infamous 2022 Oscars slap. The Weekend Update starts with its usual, if slightly eerie, headline rundown, then—boom!—the punchline zeroes in on Will Smith’s Oscar‑night shenanigans, turning the entire segment into a roast of that wild moment. (We couldn’t stop talking about it either!)

The anchors eventually drift back to more conventional news, with a standout gag about a certain politician’s claim of being invited to a coke‑fuelled orgy.

8. Get in the Cage with Nicolas Cage and Nicolas Cage

This quirky entry features the legendary Nicolas Cage—well, actually Andy Samberg in a bald cap—joining Seth Meyers to announce that there are now two Cages. Apparently, the original Nick couldn’t keep up with his own ambition to appear in every movie ever made, so he cloned himself to share the workload. But which one is the clone?

The humor peaks when the “original” Cage subtly critiques his clone’s botched impression, leaving the duplicate visibly wounded. In retaliation, the clone showers Nick with flowery, backhanded compliments, describing his “eyes that sparkle and pierce the hearts of women both old and middle‑aged alike.”

7. Pete Davidson and John Mulaney Review Clint Eastwood’s The Mule

Claiming seventh spot, this clip pairs John Mulaney—one of our personal favorites—with Pete Davidson, who both dive into their shared obsession with Clint Eastwood’s film The Mule. Their banter paints vivid pictures of how they’d look hanging out together, likening themselves to a “crazy man and his lawyer” or a “basketball coach and his most wayward trainee.”

The duo’s description of the movie’s madness convinced us to add it to our must‑watch list. Mulaney dubs it “a superhero film for old people,” while noting that Eastwood apparently wrote himself into not one but two sex scenes.

We’re now itching to see how the world’s oldest drug smuggler navigates this wild narrative.

6. Pete Davidson on Staten Island

Landing at six, Pete Davidson teams up with Colin Jost, both hailing from Staten Island, to reveal how the borough treats Davidson differently. He lays down his unfiltered feelings, even suggesting a hurricane might be the perfect way to cleanse the island, while the contrast with Jost adds extra spice.

“You represent what they could be,” Davidson tells Jost, “the kid who got out… I represent what they are—a mentally ill college dropout with a Game of Thrones tattoo before watching the show.” His self‑deprecating humor about dire‑wolf tattoos lands perfectly.

5. Colin Jost and Michael Che Switch Jokes

This clip strips away any guest stars, delivering classic headlines paired with sharp jokes—yet with a twist! As the season wraps, Jost and Che swap jokes, forcing each other to read material they haven’t rehearsed live on air.

The resulting barbs leave both anchors looking hilariously hapless, especially when Jost reacts to a graphic he knows will spark controversy. The whole exchange is a masterclass in improv roast, complete with baffling wet‑clothing moments that remain a mystery.

We love the rapid‑fire back‑and‑forth, proving that even routine news can become comedic gold.

4. Pete Davidson on Kanye West

At fourth place, this bit has aged like fine wine. The sketch opens with a tongue‑in‑cheek rationale for choosing Davidson over Che: “’Cause Che’s black, but I’m crazy,” Davidson quips, adding, “and we both know which side of Kanye’s at the wheel right now!”

The highlight is a tape review of Davidson’s reaction to Kanye’s alarming speech from the previous week. “‘I want a career!’ So I leave,” he jokes, launching into a brutal roast of Kanye’s antics, peppered with self‑deprecating humor.

Our favorite line comes when Davidson asks, “Can you imagine that T‑shirt was the second stupidest thing I was wearing?”

3. Stefon on Autumn’s Hottest Tips

Third on the list, Bill Hader returns as the eccentric city correspondent Stefon, ready to equip tourists with the season’s hottest NYC hangouts. His descriptions are delightfully bizarre—like “the vibe and sight is strange yet familiar, like seeing Seinfeld billboards in a Puerto Rican neighborhood.”

The outlandish details often crack Hader out of character, but Stefon’s habit of hiding his face behind his hands saves the day. His unapologetic openness about his sexuality adds another layer of comedy, leaving hosts squirming and audiences roaring.

2. Rachel from Friends on ’90s Nostalgia

Runner‑up features Vanessa Bayer’s spot‑on impersonation of Jennifer Aniston’s iconic Rachel Green. Her signature “uhs” and “ohs” nail the character, and while she stumbles, the real Rachel appears to set her straight.

The sketch spirals meta when Aniston mimics Bayer’s impression, prompting Bayer to double‑down, sending the whole exchange into delightful chaos. The pinnacle is Aniston’s sigh of defeat, realizing she truly sounds like herself.

1. Rebecca Larue, the Flirting Expert

Claiming the top spot, Kristen Wiig’s Rebecca Larue bursts onto the desk as the ultimate flirting guru—no tips, just pure action. The thumbnail alone (her legs splayed wide, scooting toward Seth Meyers) leaves no doubt about her intentions.

Our favorite moment is when she collapses into tears to elicit sympathy after Meyers repeatedly rebuffs her advances, only to snap back into a giddy, high‑school‑girl persona. At times, it truly feels like she’s romantically interested in the host!

11. Honorable Mention: The Late Great Norm Macdonald

Before the era of Jost, Che, Meyers, and even Tina Fey, Norm Macdonald reigned supreme as the Weekend Update host. Chevy Chase even lauded him as “the only other guy who did the segment funny.” His timing, delivery, and unflappable composure made jokes feel as integral as the news itself.

Macdonald’s favorite gag was repeatedly riffing on O.J. Simpson, even when the story had nothing to do with the infamous case. One standout moment at the 6:22 mark leaves the audience unsure whether the jokes are sexist, with his line, “Now you don’t know what the hell to do, do ya?” echoing through the studio.

His legacy endures as a benchmark for sharp, deadpan satire that still inspires today’s Update anchors.

When you think about the long‑running juggernaut that is Saturday Night Live, the phrase “top 10 borderline” immediately conjures up a mix of laughs, gasps, and occasional regret. The show has been on the air for nearly five decades, spawning countless iconic bits and unforgettable personalities. Yet, tucked among the beloved classics are a handful of characters whose humor walks a thin line between funny and offensive. Below we break down each of these ten sketches, preserving the original spirit while giving you a fresh, conversational look at why they’re both memorable and controversial.

What Makes a Character Top 10 Borderline?

It’s a combination of cultural context, the era’s comedic standards, and the way a sketch leans into stereotypes or taboo topics. Some bits were born in a time when audiences were more permissive of crude jokes, while others deliberately pushed boundaries to provoke a reaction. Whether it’s a caricature that leans on race, gender, sexuality, or disability, each entry on this list showcases a moment when SNL flirted with the edge of good taste.

10 The Samurai

Back in the 1970s, comedy writers could get away with a single, broad‑stroke racial caricature and instantly score a hit. John Belushi’s “Samurai” was precisely that: a wildly exaggerated, phony Japanese‑sounding mumble that relied on a cheap accent for laughs. Each sketch dropped the samurai into a different modern job—hitman, hotel owner, disco dancer—yet the core gag never evolved beyond the absurd premise of a feudal warrior trying to fit into contemporary society.

Belushi poured his usual physical energy into the role, but the script gave him virtually no lines. The entire performance hinged on his exaggerated, nonsensical mimicry of a Japanese accent, with the humor stemming from the sheer crudeness of the portrayal rather than any clever writing. The sketch would meander for five minutes, ending with a hollow punchline that left the audience with an uncomfortable mix of amusement and indignity.

9 The Continental

Christopher Walken, a seven‑time host of SNL, crafted a recurring persona known as “the Continental.” This character, a self‑absorbed, vaguely ethnic gentleman, repeatedly turned a supposed romantic evening in his lavish suite into a nightmarish #MeToo scenario. The sketches always began with the Continental fumbling through a date, only to reveal a pattern of stalking, drugging, and even chloroforming his guest.

When the woman tries to leave, the Continental physically blocks her exit, even going so far as to lock her in and attempt to swallow the key. The camera’s point‑of‑view places the viewer directly in the woman’s shoes, making each perverse advance feel all the more invasive and uncomfortable. The recurring gag highlights a darkly comic take on consent and power dynamics, making it a prime example of borderline material.

8 The D‑ck In A Box Dudes

The Lonely Island’s viral hit “D‑ck in a Box,” featuring Justin Timberlake, is as catchy as it is unsettling. While the song’s upbeat production and clever wordplay make it a fan favorite, the premise is unmistakably rapey. The skit asks the age‑old question: how do you convince a woman to accept a penis as a gift?

The answer, according to the sketch, is to hide the organ inside a decorative box and present it as a thoughtful present. By doing so, the “heroes” sidestep legal terms like flashing, indecent exposure, and non‑consensual behavior, turning a predatory act into a comically absurd gag. The result is a blend of ear‑worm melody and deeply uncomfortable subject matter.

7 Stefon

Bill Hader’s “Stefon” became a cultural touchstone, especially when paired with Seth Meyers’ deadpan introductions. The character’s over‑the‑top enthusiasm for New York’s nightlife made him a fan favorite, yet the bit leaned heavily on stereotypes. Stefon’s flamboyant homosexuality was used as a punchline, and he repeatedly used the term “midget” despite it being outdated for years before the sketch aired.

Even when Meyers warned him that the word was offensive, Stefon brushed it off, occasionally swapping it for “fun‑sized.” The recurring storyline of Stefon’s relentless attempts to seduce Meyers—built on the premise that “no” equals “yes”—further cemented the sketch’s reliance on problematic tropes, making it both hilarious and questionable.

6 Stuart Smalley

Al Franken’s “Stuart Smalley” was a self‑help guru who spoke in a lispy, affirming tone while donning Malibu‑Ken attire. The humor derived from Smalley’s unabashed emotional openness, a stark contrast to the hyper‑masculine comedy of the era. However, the character’s entire premise hinged on his gay identity, using it as the central joke.

Adding to the controversy, Smalley’s backstory involved a father who was an alcoholic and a mother who suffered abuse. In one sketch, Smalley mentions his father beating both him and his mother, framing the tragedy as comedic fodder. This blend of personal trauma and stereotypical gayness made the sketch both revolutionary for its time and uncomfortable by today’s standards.

5 Pat

Julia Sweeney’s “Pat” was an experiment in gender ambiguity. The character’s name, wardrobe, and behavior were deliberately androgynous, and the humor sprang from the cast’s attempts to determine Pat’s biological sex. The sketch played on the outdated belief that gender is strictly binary, forcing other characters to ask probing, often absurd, questions.

While the premise was rooted in a lack of understanding about gender fluidity, the recurring game of coaxing information from Pat added a layer of comedic tension. This “guess‑the‑gender” routine at least gave the sketch a structure that eclipsed the more simplistic offensiveness of characters like the Samurai.

4 Governor David Paterson

Fred Armisen’s impersonation of New York Governor David Paterson turned a real‑life political figure into a source of disability‑based jokes. Paterson, who served as governor in the late 2000s and was legally blind, became a caricature for physical comedy. Armisen’s sketches featured Paterson bumping into furniture, squinting through binoculars, and generally stumbling about.

These bits mined the governor’s visual impairment for laughs, relying on slapstick mishaps rather than any substantive political satire. While the performance showcased Armisen’s physical comedy chops, it also highlighted how SNL could cross into insensitive territory by making a real person’s disability the punchline.

3 The Word Association Guy

In SNL’s first season, Chevy Chase hosted a sketch where he conducted a job interview with Richard Pryor. The interview turned into a rapid‑fire word‑association game that quickly descended into a barrage of racial slurs. The tension escalated until Chase uttered the N‑word on live television—a moment that shocked both the audience and network executives.

Despite its brevity, the sketch became a historic television moment, embodying the punk‑rock spirit of early SNL. Its raw, unfiltered profanity pushed the boundaries of what was permissible on prime‑time TV, cementing its place in comedy history as both groundbreaking and controversial.

2 The Ambiguously Gay Duo

Robert Smigel’s “The Ambiguously Gay Duo,” voiced by Stephen Colbert and Steve Carell, lampooned the superhero genre with a pair of hyper‑muscular men whose actions were unmistakably homoerotic. The sketch parodied classic Batman‑style dynamics, replacing capes with flamboyant catchphrases and overtly gay subtext.

The duo’s antics included driving a penis‑shaped car, performing ballet to dodge bullets, and using a flurry of phallic and butt‑shaped props to defeat villains. Their obliviousness to the homoerotic implications of their behavior made the sketch both a satire of superhero tropes and a commentary on the discomfort surrounding gay representation in media.

1 Canteen Boy

Alec Baldwin’s “Canteen Boy” sketches often mocked mental disability, but the most egregious episode involved Baldwin playing a scout leader who attempted to molest the titular character. The scene featured Baldwin stripping, trying to get Canteen Boy drunk, forcing him into a sleeping bag, and even engaging in overtly sexual behavior such as nuzzling and finger‑sucking.

Set against a backdrop of real‑world scandals involving scout leaders, the sketch amplified the horror of sexual abuse, making it painfully clear why it sparked outrage. The combination of a mentally challenged character and explicit molestation made this bit one of the most controversial in SNL’s history, raising questions about the limits of comedy.