Saturday Night Live: Defining Show Moments of the 21st Century

Season 27: The Show Must Go On

Well, that’s one way to start a new century of shows.  After the 2001 terrorist attack on New York, it was fair to ask if it was appropriate to go ahead with the SNL season premiere on September 29th. The host was a terrified Reese Witherspoon, completely reasonable considering a live TV show was another attractive terror target.  (Host Drew Barrymore and the entire cast had to be evacuated just weeks later due to an anthrax scare.)

Before Rudy Guiliani turned into a national villain, America’s Mayor was capable of delivering a tension-breaking punchline.  After Paul Simon performed “The Boxer” in a moving tribute to New York’s first responders, Lorne Michaels asked Rudy if the show could go back to being funny again.

Giuliani responded:  Why start now?

Season 28: Adrien Brody is an Idiot

Brody committed two SNL no-nos when he introduced musical act Sean Paul.  First, he completely improvised a “comedy” bit without the knowledge of Lorne or the cast.  Second, the gag was racist and unfunny, involving a dreadlocks wig, a terrible Rasta accent, and stunned audience silence: 

“Respect all respect. My auntie. Respect all aspect, respect me neck, respect me knees, Big up Jamaica massive! Big up Kingston Massive! We got the whole family now, ya here! Big respect to my man Sean Paul the dance floor killer!” 

Welcome to the permanently banned list, Adrien!

Season 29: Enter Kenan

A relatively uneventful season is remembered for the first appearance of Kenan Thompson, who sets SNL longevity records every time he sets foot on the 30 Rock stage.  Sketch #1 was a dialogue-free appearance during Jack Black’s season-opening song-ologue (worth a watch!); Kenan now has more than 1,500 of these babies under his belt.

Season 30: Ashley Simpson’s Lip-Sync Fail

Was Ashley Simpson the first musical guest to lip-sync on SNL? We’re guessing not.  But she was the first to create this kind of cringe-comedy catastrophe. 

We kind of want to slink off the stage too.  

Season 31: Samberg and Parnell Jumpstart the Internet

YouTube was just another struggling web start-up, morphing from dating app to video hub at a time when most everyone was still on a dial-up connection. Then this happened:

A couple of weeks and two million views later, YouTube as we know it was born. “YouTube would have found its way without Lazy Sunday," says Parnell, “but we gave it a shot of adrenaline.”

Season 32: It’s a (Bleep) in a Box

Justin Timberlake and Andy Samberg were about the same age, growing up in the era of 90’s R&B.  “So we had this idea about how to do a joke about guys who were still stuck in that era,” remembers Timberlake. “And then it was like, ‘How do you get away with them being idiots?’” 

The first time they showed Dick in a Box we were on the studio floor watching and we had this electrifying feeling,” says Lonely Island’s Jorma Taccone. “And we thought, ‘This is special.’”

Season 33: What Season?

The defining “moment” of Season 33 was the WGA’s writers’ strike. With only 12 episodes, Season 33 set a record for SNL futility. The season’s highlight was likely a two-hour live show performed at Amy Poehler’s UCB Theater to benefit behind-the-scenes crew who were out of work due to the stoppage.  

Saturday Night Live--On Strike! gave cast members a chance to play without the restrictions of broadcast television.  Said one audience member: “It was a little dirtier than usual.”

Season 34: I Can See Russia From My House

Sometimes, comedy becomes reality.  Tina Fey’s wicked funhouse version of Sarah Palin may have swung an election, with some voters confusing Fey’s bumbling imitation with the bumbling real thing.  Snopes actually had to publish articles clarifying which events were Fey jokes and which were actual Palin foolishness. 

Season 35 The Internet Gets What It Wants.

And what the Internet wanted was Betty White.  Back in the days when Facebook was all about pokes and prom pictures, an industrious group of users started a campaign to convince SNL to hire the beloved comedy icon.  It worked, despite Betty White having virtually no idea that Facebook existed.  Once someone introduced her to the site, White admitted that “it sounds like a huge waste of time.” The 88-year-old White killed it and the episode was one of SNL’s highest rated in years.

Season 36: Bill Hader panics

Even comedy legends are plagued with self-doubt. Hader has been open about his anxiety while performing on the show, and on Season 36’s tenth episode, he confesses to an onscreen panic attack.  

"If you look at the Julian Assange sketch I did when Jeff Bridges was hosting, you can see I’m really nervous," he told The Today Show. "I was covering my face a little, thinking, 'Oh, I’m having a panic attack. Really? Really? Really? Right now? Thanks, comedy gods.'”

Season 37: She’s a Rainbow

No cast member before or since has received a send-off like Kristin Wiig, with Mick Jagger presiding over her “graduation ceremony” before serenading her to the strains of “She’s a Rainbow.”  Wiig enjoys a final dance with every freaking member of the cast before ascending into SNL heaven. 

“I don’t think there was a lot of thought given to how emotional it would be until suddenly there it was and we were doing it,” remembers Lorne. “It was just a magical thing.” 

Season 38: Fred Passes the Obama Baton to Jay

SNL has a long, troublesome history with blackface, from Billy Crystal’s Sammy Davis Jr. (with Sammy’s full blessing, for what it’s worth) to biracial Fred Armisen’s Barack Obama. Armisen’s Obama imitation was not particularly great, which made the season-opening symbolic handoff to Jay Pharoah all the more welcome.  

Season 39: Wherefore Art Thou, Black Female Cast Member?

This season’s defining moment happened offstage.  After years of throwing a wig on Tracy Morgan or Keenan everytime a sketch featured a black female character, both fans and cast members had had enough.  People behind SNL hiring “need to pay attention” to the cast’s lack of diversity, said Pharoah. “And I believe they need to follow up with it like they said they were going to do last year.” 

Lorne Michaels heard the noise, holding an audition exclusively for black female performers before casting Sasheer Zamata in January, as well as adding Leslie Jones and LaKendra Tookes to the writing staff.  

Season 40: Pete Would Do It For A Million Dollars

While Pete Davidson was never a particularly strong sketch comic, he demonstrated on his very first show that he had something even more potent: star power.

Playing his best character -- himself -- Pete showed up on the Weekend Update desk letting Michael Che know just what sexual acts he’d be willing to perform for a million bucks. “Davidson made quite an impression in his first appearance, and the crowd definitely loved the bit,” said The Hollywood Reporter. “This bodes well for Davidson’s future on the show.”

Yeah, Pete did OK.

Season 41: President Who?I

The Home Alone 2 star hosted almost one year to the day before he was elected President of the United States.

Season 42: The Hit Job

Alec Baldwin was never an official cast member but he might as well have been, signing a contract to appear as Donald Trump for the entire season (and beyond).  

Darrell Hammond, the show’s Trump for several seasons back in The Apprentice days, didn’t take the news well. “I just started crying,” he says. “In front of everyone. I couldn’t believe it. I was in shock, and I stayed in shock for a long time. Everything wiped out. The brand, me, what I do. Corporate appearances canceled. It was a hell of a shock, and all of it was apparent to me in one breath. That ends me.”

Someone else who didn’t take it well: Trump, an actual sitting President who regularly tweeted gripes like:  "Watched Saturday Night Live hit job on me. Time to retire the boring and unfunny show. Alec Baldwin portrayal stinks."

Season 43: Getting Their Irish Up

This season’s controversy revolved around Saoirse Ronan’s funny Aer Lingus sketch, which for some reason angered the airline.

Not sure what the problem was here -- the idea that the Irish like dogs? -- but Ronan wasn’t having it. "Whenever (Lorne) would ask me (what I wanted), I would always say I really want to use my own accent as much as possible,” she said. “And I want there to be at least one Irish sketch in there." We’re assuming the airline got over it. 

Season 44: Make America Kanye Again

It wasn’t the first time Kanye West made headlines as an SNL guest, but still. A MAGA cap and a surprise rambling speech supporting Trump?  No one saw that coming. It was a big enough deal for Pete Davidson to address on the following week’s show, explaining “Do you know how wrong you have to be about politics for me to notice?”

Season 45: The Return of Eddie Murphy

The season’s defining moment could have been the hiring and firing of Shane Gillis, a comic who landed one of the prime gigs in comedy before video clips emerged of Gillis scoring the offensive trifecta (jokes that managed to be racist, sexist, and homophobic).

But that controversy was overshadowed by the homecoming of Eddie Murphy, arguably the biggest star the show had ever produced.  Murphy had been away for 35 years, largely due to a grudge stemming from a David Spade joke.  (Sure, it was sorta mean, but what was Spade supposed to do on Hollywood Minute, compliment all the stars on their taste in fine art?) Cast members return all the time, even after long absences (Danny Aykroyd, Adam Sandler), but this one felt like a prodigal son finally coming home.

Season 46: A Chill, Normal Dude?

It wasn’t quite the Donald Trump scandal, but Elon Musk’s turn as host was as controversial as it was weird.  Cast members including Bowen Yang and Aidy Bryant took to social media to express their displeasure over Lorne’s choice of host, a billionaire who had recently opened a Tesla plant mid-pandemic, leading to more than 400 cases. Still the show went off mostly without a hitch. “To anyone I’ve offended, I just wanted to say, I reinvented electric cars and I’m sending people to Mars on a rocket ship,” said Musk in his monologue. “Did you think I was also going to be a chill, normal dude?”

Season 47:  The Kiss

In a season where Kacey Musgraves performed wearing only a pair of cowboy boots and Colin Jost broke the record for most Weekend Updates, the season was overshadowed by an Aladdin spoof.

Tabloid monsters Kim Kardashian and Pete Davidson made no sense, which in Kardashian Land means they made perfect sense. SNL stars like Will Ferrell and Tina Fey were never known for their love lives -- did we ever know who Chris Kattan was dating? -- but Davidson’s offscreen controversies often threatened to overshadow the show itself.  If SNL had one moment last season that inspired the zeitgeist (and Ye’s threats of righteous vengeance), it was The Kiss. 

For more ComedyNerd, be sure to check out:

15 Jokes For The Hall of Fame 9/21/22

Take More Chances, Eddie Murphy!

Saturday Night Live: 14 Characters That Deserve Their Own Movies (And Those That Didn’t)

For ComedyNerd exclusive content and more, subscribe to our fancy newsletter:

Sign up for the Cracked Newsletter

Get the best of Cracked sent directly to your inbox!

SIGN ME UP

Top image: Broadway Video