“You know who was at the Vanity Fair party? Monica Lewinsky. She was sitting right next to me. I was at Table 14; she was under Table 12.”  — Jay Leno

In the late 1990s and early 2000s, late-night comics from Leno to David Letterman to the gang at Saturday Night Live made a living by churning out jokes about White House intern Monica Lewinsky. The wisecracks were all about the 24-year-old’s sexual relationship with the President of the United States, a consensual affair if only in the way that an affair between a young, unpaid intern and an extremely powerful boss can be considered consensual. For members of the punch-up comedy community, William Jefferson Clinton was fair game as the butt of jokes. But the majority of punchlines — about her promiscuity, about her weight, about her blue dress — were reserved for Lewinsky. 

As it turns out, a road trip to Canada in search of handbag fabric was the slyest, most subversive Monica Lewinsky comedy of the entire turn-of-the-century brouhaha. But before we get into Tom Green’s spin on the chaos surrounding Lewinsky, let’s look back at the different ways television comics took on the scandal.

’Oversexual Airhead’

Saturday Night Live practically turned Lewinsky into Mango or the Spartan cheerleaders, a recurring Molly Shannon character who appeared in no less than 15 sketches between February 1998 and January 2000. With her trademark beret cocked to one side, Shannon’s character was dumbed down to what Vanity Fair characterized as an “oversexual airhead” who flirted (at the least) with leaders around the world. 

Lewinsky eventually appeared on the show as herself, presumably in an attempt to take control of her narrative. The tone of the jokes changed when she was actually in the building. In the cold open, she gets to call Clinton a “big creep.” Appearing with the Ladies Man, Lewinsky is the voice of reason, advising against workplace affairs and sharing your private business with “friends” like Linda Tripp.

But critics weren’t kind. The Washington Post’s Tom Shales admitted that Lewinsky’s comic acting was better than expected, but “she looked extremely chubby of face and fanny” (just one of many shots he took at her looks). But her bigger offense, according to Shales, was enjoying herself in the face of “what’s she’s famous for.” To the critic, Lewinsky was milking her new publicity for all it was worth: “She always has the smirk of the cat who swallowed the canary and couldn't be happier about it.” 

Writer James Downey fought against her SNL guest appearance, believing the cameo was “a little trashy.” He noted his dissent by writing a sketch about Lewinsky winning “the presidential kneepads,” then got frustrated when her publicist said no way. “I thought if I were Monica Lewinsky," says Downey in Live From New York, an SNL oral history, “I would have a little more sense of humor.” 

As for Clinton? Darrell Hammond’s version didn’t exactly hold the president’s feet to the fire. This rascally horndog always got the ladies, and even when he was in trouble, he celebrated his lecherous conquests. In a sketch that featured Clinton reading sexual harassment accuser Paula Jones’ actual deposition — “he placed my hand on his penis” — he paused to give us a thumbs up and exclaim, “This is hot!”

Broadway Video

Frat-Bro-in-Chief

Was Lewinsky a casualty of the boys’ club mentality at SNL? Perhaps, but Tina Fey was head writer for one of those seasons, and chided Lewinsky in 2011’s Bossypants for being a little too open with her personal details: “I’m just saying. Linda Tripp may not have been the intelligence-gathering mastermind you thought she was.”

Back in the late 1990s, things got meaner for Lewinsky during the week. Leno notoriously made lazy Lewinsky jokes for years, devoting an entire monologue to the day she was interviewed on ABC’s 20/20. He wasn’t exactly apologetic about it either, telling Oprah in 2003, “The Monica Lewinsky scandal was the golden age of comedy.” 

Letterman wasn’t much better, doling out jokes like: “You may think you have a stressful job, but since she’s been a senator, Hillary Clinton, they say, put on 30 pounds. In fact, she has gotten so heavy that today Bill hit on her.” And anything with the words “Monica Lewinsky” made for an easy laugh on Dave’s Top Ten lists, occasionally as the subject of the list itself: 

Worldwide Pants

Joan Rivers was in the club as well, making nasty Lewinsky jokes in her early 2000s routines (“Why would anyone would want to buy a hat from Monica Lewinsky? A vacuum cleaner, maybe. But a hat?”) and continuing well into the 2010s.

‘She Was a Human Being’

Then there was MTV’s The Tom Green Show

In a 2000 special episode, Green brought Lewinsky to his hometown of Ottawa to shop for fabric for a new line of Lewinsky handbags. There’s a running gag that the two are holding a press conference to possibly reveal a relationship — they’re only making handbags, folks! — but Lewinsky is completely in on the joke. She’s funny and relaxed, game for whatever light-saber-fight-in-a-donut-shop nonsense Green puts her up to, and there’s nary a dress stain joke to be found. The lack of comment on the scandal was the comment, at least in part.

The pivotal moment in the special? It might be when Canadian paparazzi surround their car, snapping dozens of pictures. Green leans into Lewinsky and confides: “The funny thing about this is we’re making fun of them.”

“We were about the same age, you know?” Green tells me. The out-of-nowhere Canadian comic was caught in his own kind of whirlwind, and knew what it was like to be suddenly famous and the subject of thoughtless insults. So bringing Lewinsky in on the joke, even changing the joke entirely, was intentional. “There was a different kind of connection that we had,” Green explains. “Because (others) were just looking at her like some sort of a punchline for a comedy show when she was a human being.”

'Bury the Beret and Burn the Dress'

For many comedians, Lewinsky’s late 1990s treatment is an uncomfortable mark on their resumes. After Lewinsky wrote an excruciating essay about her public disgrace for Vanity Fair in 2014 (her mother was “afraid that I would take my own life — a fear that I would be literally humiliated to death”), many in the comedy world took a good hard look at their own role in her public shaming. 

Letterman was one of the first to express remorse after the essay was published, confessing to Barbara Walters on his Late Show that “I started to feel bad because myself and other people with shows like this made relentless jokes about the poor woman. And she was a kid. I feel bad about my role in pushing the humiliation to the point of suffocation.”

As for SNL, Lorne Michaels isn’t exactly apologetic, but he does say the show would treat the Lewinsky scandal differently today. “Standards and boundaries change,” Michaels recently told Dana Carvey and David Spade on the Fly on the Wall podcast, pointing to John Goodman in drag as Linda Tripp as one example of a bit SNL wouldn’t attempt now. Meanwhile, SNL’s 1999 head writer Adam McKay told the Los Angeles Times that he has his own regrets, acknowledging “clearly there was some awareness that this is probably going to haunt this poor girl for years, which seems kind of ridiculous given that it should haunt Bill Clinton.”

John Oliver put Leno (and to a lesser extent, himself) on blast for their roles in the humiliation. “My hands are not clean here either,” he admitted on Last Week Tonight, regretting a Daily Show bit marking the 10th anniversary of the scandal. “It’s gross!” Oliver noted that many comics had expressed regret — but not “the most relentless,” Jay Leno.

Leno was hitting talk shows at the time bemoaning the loss of civility in comedy, but Oliver was having none of it. How could a guy complain about civility after doing a bit with a fake Lewinsky book titled The Slut in the Hat? In response,  Oliver offered his own phony book: Oh, the Places You Can Go F*** Yourself, Jay Leno

Green, however, isn’t passing judgment. “Comedy evolves and changes,” he says. “You can look back at something that was said in the 1950s, 1960s or 1980s, and it's just a completely different sort of behavior. And that's a good thing because that means that we're progressing as a culture.” 

“There can be a mean-spiritedness to comedy at times,” Green continues. “That show we made on MTV was crazy and shocking. We were doing outrageous things, confusing people, creating chaos, but it was always meant to be coming from a place of silliness and absurdity.” 

Today, Green remains rightfully proud of the Lewinsky special. In fact, both he and Lewinsky, who remain friends, still remember it fondly: 

Twenty-two years later, the special's laughs still hold up — certainly better than the tired slut-shaming of the late-night gags. And just in case some people weren’t getting the joke, Green contextualized the message by ending the special with a quote from Oscar Wilde: “The public have an insatiable curiosity to know everything. Except that which is worth knowing.”

Top image: MTV Productions

Get More Comedy: Sign up for ComedyNerd

The ComedyNerd newsletter is your weekly look at the world of stand up, sketch, and more. Sign up now!

Forgot Password?