15 Funny Jokes and Sketches That Are Peak ‘90s Humor

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15 Funny Jokes and Sketches That Are Peak ‘90s Humor

Look, we didn’t say they were all good. We didn’t say they “need a reboot.” We didn’t say these comedians are proud of their work, three decades on. All we can promise is that back in the ‘90s, this stuff was the pinnacle of comedy.

Adam Sandler, ‘The Chanukah Song’

Sandler chronicled the many perks of being Jewish, as well as some of Judaism’s all-time biggest celebs, in a five-part song that now spans two decades.

Ralph Wiggum, ‘Me Fail English? That’s Unpossible’

This Season Six banger is coming up on 30 years of being a go-to quip from the office funny guy.

Janeane Garofalo’s Extremely ‘90s Hell

“My hell is going to be the StairMaster wing of Dante’s inferno, where they’re gonna tape my feet to the pedals and the only music I get is Michael Bolton, karaoke style.”

Mitch Hedberg’s ‘Late Show’ Debut

Hedberg’s 1997 set on Letterman is six minutes of nostalgia overload, including his personal experience with Kurt Cobain-esque long hair: “A lot of people associate long hair with drug use. I wish long hair was associated with anything other than drug use. Like an extreme longing for cake. Strangers will look at me and say, under their breath, ‘That guy eats cake. He is on bundt cake.’ Mothers saying to their daughters, ‘Don’t bring the cake-eater over here anymore. He smells like flour.’”

Stuart, ‘MADtv’

Michael McDonald’s rosy-cheeked, sugar-brained cherub, Stuart, delighted a generation with his castrato delivery of heady jokes like “Look what I can do!” and “Lemme do it!” You kind of had to be there.

The Roxbury Guys, ‘Saturday Night Live’

Looking back, yeah, maybe a Get Off the Shed Guy movie would have been a more compelling exploration of a Will Ferrell character. But at the time? Overtly horny slapstick was king.

Prometheus and Bob, ‘KaBlam!’

These stop-motion shorts explored conundrums between two characters who couldn’t talk, and who, on paper, couldn’t be less relatable: a caveman from the ancient past and an alien from the distant future. Somehow the two found common comedic ground in the ‘90s.

Goodburger, ‘All That’

This sketch series helped solidify Kenan Thompson and Kel Mitchell as comedic powerhouses, which landed them their own spin-off, Kenan & Kel, and helped Thompson ultimately become the longest-tenured cast member in SNL history. Some say he’s still wandering the halls of 30 Rockefeller Center to this very day…

Milhouse Van Houten, ‘Everything’s Coming Up Milhouse!”

Seeing Milhouse celebrate the small wins — his bone-dry cuffs despite water flooding his house — would come in handy for ‘90s kids who were about to weather the storms of Y2K, 9/11 and Justin Timberlake’s solo career.

Wanda Sykes on the Hypocrisy of Comedy Central at Its ‘90s Peak

She called out the crassness of South Park when she was proactively scolded ahead of Comedy Central Presents: Wanda Sykes: “Comedy Central told me I had to watch my language, because, the woman said, ‘They had standards and practices.’ I was like, ‘Wait a minute. You’re Comedy Central! Aren’t you the network where your number one show is a cartoon with a talkin’ piece of shit?’”

Mary Katherine Gallagher, ‘Saturday Night Live’

Molly Shannon’s nervous, pit-sniffing, Catholic school girl character might not have shined as brightly, had it been introduced in another decade. But in the ‘90s, it was a 20-appearance surefire hit on SNL and a cult classic film, Superstar.

‘Weinerville’ (Pick a sketch)

Just watch the intro and tell me this isn’t the most concentrated hit of ‘90s chuckle fodder you’ve snorted in 25 years. An entire sketch show based around a childish pun, with a “studio band” that blends punk, hip-hop and ska. Put it back in the time capsule, 2024 isn’t ready for any of this.

The Delicious Dish, ‘Saturday Night Live’

Ana Gasteyer and Molly Shannon fawning in deadpan over Alec Baldwin’s Schweddy Balls probably humanized him enough to get him through one or two more decades of impressively chaotic controversies.

Ellen DeGeneres Was a ‘90s Comedy Powerhouse

“My grandmother takes care of herself. She started walking five miles a day when she was 60. She’s 97 today. We don’t know where the hell she is.”

She’s funny! She’s clean! She hasn’t yet publicly bullied Taylor Swift!

Ms. Swan, ‘MADtv’

Just kidding, this character aged like milk that came out of the udder 10 years past its expiration date. A generation of third-grade class clowns was doing this impression on the playground. Kind of explains a lot about modern-day America, if you think about it.

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