Top 10 SNL Moments of Century (So Far)

This Halloween-themed sketch became an “SNL” classic thanks to the introduction of David S. Pumpkins and his dancing skeletons. He’s not scary in the traditional sense but does a great job of freaking out the visitors on this haunted elevator ride. It’s hard to believe that Hanks struggled to connect with the character as he plays him so well. Bobby and Mikey give outstanding performances too. The dancing, excellent facial expression, hilarious self-assuredness, and total randomness are priceless. For many, watching this sketch has become a Halloween tradition. We might not have known who David S. Pumpkins was before, but we certainly weren’t going to forget him now.

When making your “SNL” hosting debut, you definitely want to make an impression. And arguably, Kristen did just that, just maybe not in the way she had intended. Her funny and entertaining monologue ended up being overshadowed by an unexpected adlib at the end. She later divulged that she’d been reminded to keep it clean but we guess she just got caught up in the nerves and excitement. No one seemed more shocked than the actress but the audience lapped it up. Luckily for Stewart, she’s in good company. She rocked the rest of the night and was even invited to host again. Live TV, eh?

Picture it: It’s 2004 and Jude Law has just introduced musical guest Ashlee Simpson for the second time. The music starts to play and it’s “Pieces of Me” and you’re thinking, wait, didn’t she already perform this one? And that’s when you discover that she’d been lip-synching. We might have been able to forgive this moment if she didn’t then proceed to do an awkward hoe-down jig off of the stage. Worse still was when she returned at the end of the show to pin the blame on her band. Simpson’s career struggled to recover due to this moment that’s forever cemented in infamy.

After watching this sketch, it’s hard to believe that it took Mulaney this long to get it on air. He first pitched it back in 2010, as a writer on the show. But it wasn’t until he hosted in 2018 that it was finally greenlit. It starts quite simply with a guy ordering lobster in a diner. Then before you know it, you’re watching an elaborate “Les Misérables” parody. Jean Valjean’s in hot water, Clawsette makes an appearance and there’s even a barricade. It’s quite an escalation but that’s exactly what we love about Mulaney’s zany humor. Hilariously the sketch even won an award from PETA.

It’s not that unusual for politicians to try and connect with voters through their funny bones. And what better place to do so than Studio 8H? Back in 2007, this cold-opening saw Democrats come together at the Clintons’ Halloween party. Among their many guests, they’re approached by a mystery man wearing an Obama mask. You can hear the audience’s surprise when he removes it to reveal that it’s actually the real Barack Obama underneath. We imagine that the former President has accumulated many highlights throughout his lengthy career. But shouting out the iconic “Live From New York” phrase has got to be up there.

If you thought you knew Natalie Portman, think again. When she hosted in 2006, she took us all by surprise in this hilarious and badass Digital Short. In an interview that takes quite a drastic turn, she sheds her good-girl image to aggressively rap about her preferred activities. The contrast of the calm composed actress we thought we knew with this profanity-filled rage spree is perfection. It’s so good that in 2018, she even recorded a sequel and, let’s just say that motherhood has made her even more hardcore. If someone could just explain Andy Samberg’s Viking outfit to us, we’d be super grateful.

Joining “SNL” in 2005, The Lonely Island was responsible for several Digital Shorts that went viral. These include their ode to Jack Sparrow, the iconic “D*** in a Box,” and of course, “I’m on a Boat.” In a send-up of clichés often associated with rap videos, Samberg, Schaffer, and T-Pain, vehemently rap about being on a boat. Shortly after its release, it became the number one viewed video on YouTube. It also peaked at number one in the U.S. iTunes chart, received a Grammy nomination, and even went Platinum. We bet that T-Pain was glad to be on board for this one.

One of “SNL’s” standout characters of the 21st century has to be Bill Hader’s city correspondent Stefon. Audiences loved his quirky personality, outrageous suggestions, and how easy it was to make him break. In his final regular appearance, Stefon storms off “Weekend Update” to marry Anderson Cooper. Incidentally, witnessed by many of the characters he’d described throughout the years. However, Amy convinces Seth to go after him, which he does in true rom-com style. Returning together to “30 Rock,” they finally profess their love for each other. We were sad to see Hader leave but glad that Stefon got the send-off he deserved.

Before we unveil our top pick, here are a few honorable mentions.

There Are Two Sides to Every Story, but We Still Didn’t See This One Coming

Every Moment of This Episode Was Just Perfection

If the Cast Couldn’t Keep It Together, What Hope Did We Have?

Probably Not the Role Model They Were Expecting

This One Was Actually Fauci’s Idea & SNL Was Happy to Follow Through

Ask any fan what quote defines “SNL” in the 21st century and be prepared to have “More Cowbell” yelled at you, a lot. A parody of VH1’s “Behind the Music,” this sketch answers the question we’d all been pondering. What’s the deal with the guy softly playing the cowbell on Blue Öyster Cult’s “(Don’t Fear) The Reaper?” Well, at least that’s what crossed Will Ferrell’s mind. The combination of his ever-shrinking tiny shirt and overly-enthusiastic performance, paired with Christopher Walken’s deadpan delivery launched this sketch into legendary status. It’s so funny that even the cast keeps breaking. Still, if you see Walken, maybe avoid shouting “More Cowbell” at him.