Pop Culture

The Appalling Monica Lewinsky Jokes—and the Comedians Who’ve Apologized

In the years since mercilessly skewering Lewinsky and Linda Tripp—a chapter revisited on Tuesday’s Impeachment—some comedians have expressed regret. Others have remained notably silent.

It is staggering to look back on the television jokes that targeted Monica Lewinsky in the late ’90s—a tasteless litany of punch lines targeting a 20-something woman who did not choose to become a public figure. Lewinsky was also legally bound from speaking up in defense of herself—so she had to sit back silently, night after night, as David Letterman, Jay Leno, and more mostly male television hosts lobbed insults her way. (An especially enraging statistic: According to researchers at George Mason University, Lewinsky was targeted over 450 times by Leno in his 22 years as host—making her the seventh most frequent target of political jokes on his iteration of The Tonight Show. Osama Bin Laden, for comparison, trailed the former White House intern at number 20.)

In Tuesday’s episode of Impeachment: American Crime Story, poignantly titled “The Assassination of Monica Lewinsky,” both Lewinsky (Beanie Feldstein) and Linda Tripp (Sarah Paulson)—prisoners in their own homes during the Bill Clinton media circus—watch surreally from their sofas as their names and faces are suddenly thrust into a searing spotlight.

But in the two-plus decades since those jokes were made, some comedians have taken responsibility for their cruel comedy. Ahead, a rundown of some of the hosts and comedy programs that targeted Lewinsky and Tripp—and the parties who have since publicly taken responsibility for their hurtful barbs over the years.

Jay Leno

Among Leno’s many Lewinsky-targeted insults:

“You know who was at the Vanity Fair (Academy Awards) party? Monica Lewinsky. She was sitting right next to me. I was at table 14; she was under table 12.”

“Monica Lewinsky has gained back all the weight she lost last year. I believe that’s the cover story in Newsweek. In fact, she told reporters she was even considering having her jaw wired shut, but then, nah—she didn’t want to give up her sex life.”

In 2019, John Oliver put Leno on blast after the former Tonight Show host complained about the talk show landscape—telling an interviewer that he’d like to see “a bit of civility come back.”

After Oliver admitted that his own hands “are not clean here either”—he copped to a “gross” Lewinsky gag he participated in on The Daily Show—the Last Week Tonight host cued up a montage of Leno’s ruthless insults directed toward Lewinsky.

“Those jokes have not dated well in any sense of the word,” says Oliver in the below video. “And they’re pretty rough, especially coming from a guy who just this week complained about late-night TV, saying that he’d like to see ‘a bit of civility come back.’ You know, like that time that he did a bit with a fake book about Lewinsky titled The Slut in the Hat. And if that’s what he means by ‘civility,’ may I offer my new book, Oh, the Places You Can Go Fuck Yourself, Jay Leno!

Earlier this year, Leno issued a formal apology to another party he targeted on the Tonight Show: the Asian community.

“At the time I did those jokes, I genuinely thought them to be harmless,” Leno said in March. “At the time, there was a prevailing attitude that some group is always complaining about something, so don’t worry about it. Whenever we received a complaint, there would be two sides to the discussion: Either ‘We need to deal with this’ or ‘Screw ’em if they can’t take a joke.’ Too many times I sided with the latter even when in my heart I knew it was wrong.”

Shortly after Leno released the statement, journalist Yashar Ali responded, “Waiting on an apology to Monica Lewinsky @jayleno.”

Representatives for Leno have not responded to Vanity Fair’s request for comment.

David Letterman

A small sampling of Letterman’s Late Show digs:

“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.”

“Bush went to Wisconsin, to a Harley-Davidson factory and rode a motorcycle. It’s the biggest thing a president has ridden since…I just can’t bring myself to throw that joke away.”

Letterman publicly expressed remorse for his Lewinsky jokes in 2014, after reading an essay Lewinsky wrote for Vanity Fair, which detailed the global humiliation and many repercussions she faced from the scandal.

Speaking about the essay during a Late Show segment with Barbara Walters, Letterman said, “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, she was 21, 22…”

He added, “I feel bad about my role in helping push the humiliation to the point of suffocation.”

“Good,” replied Walters. “Then we can stop.”

Saturday Night Live

Arguably the most stinging moment in Tuesday’s episode of Impeachment occurs when Linda Tripp (as played by Sarah Paulson) sits down to watch Saturday Night Live with her children and a bowl of popcorn. Tripp might have been expecting that the political fiasco would feature in some way on the sketch-comedy show—but she likely wasn’t prepared to see John Goodman portraying her in drag.

The 1998 cold open that introduced Goodman’s take on Tripp was not much kinder to Lewinsky, who was played by Molly Shannon as an oversexual airhead.

Representatives for Goodman, Shannon, and Saturday Night Live creator Lorne Michaels did not respond to Vanity Fair’s requests for comment.

In a statement to Vanity Fair, Adam McKay, who was head writer of SNL when the episode aired, said this: “I didn’t have anything to do with the writing, rewriting or advocating for that sketch. But the sad truth of the matter is the sketch definitely reflected the popular mood of the time. Now that we’ve learned of Clinton’s associations with Jeffrey Epstein, that whole period plays much, much darker.”

Three years ago, in an interview with the Los Angeles Times, McKay recalled writing another Lewinsky sketch that was cut from the show after dress rehearsal. In the sketch, which was set in the future, Lewinsky is a Nobel Prize winner with three PhDs appearing on a talk show. Despite her accomplishments, “all the hosts really want to talk about is the cigar and the dress.”

McKay was not sure why the sketch was cut, but acknowledged, “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.”

In a 2001 interview with Larry King, Tripp said that the Goodman sketch was so unflattering that it played a part in her decision to get plastic surgery.

“Kids are so sensitive about their parents,” Tripp said. “And my kids always thought I was pretty. And they were so completely shattered by the John Goodman and the horrible press.” Speaking about the surgery, she said, “I just felt so badly for them. I just wanted to fix it.”

Lewinsky herself made a cameo on SNL in 1999—though the former White House intern was not exactly welcomed by everyone on staff. In the 2002 SNL oral history, Live From New York, former staff writer James Downey recalled his displeasure with Lewinsky’s appearance:

“I registered my dissent about Monica coming on by writing a couple of
sketches, neither of which got on the air. One was about Monica
winning “the presidential kneepads,” and the history of the kneepads
and that kind of thing…. [A]nyway, Monica Lewinsky’s publicist read
the sketch—I actually watched the guy read it—and after he flipped
through it he just went, “Uh-uh. Not interested.” And it was like,
“Oh, I’m sorry, does she have some long glorious résumé of
achievement—or did she blow the president?” There was this attitude of
like, “Monica Lewinsky does not do kneepad stuff.” I thought if I were
Monica Lewinsky, I would have a little more sense of humor.”

Downey also did not respond to Vanity Fair’s request for comment.

Bill Maher

After the Starr Report was released, Maher actually seemed to blame Lewinsky for the Clinton affair. In 1998, he claimed:

“She comes off as someone who basically blackmails the president of the United States…And Katie Roiphe wrote a great article the other day, and she said there should be a term connoting the opposite of sexual harassment—when a person of less power uses her sexual attractiveness or personal relationship with the person in greater power to get ahead. No pun intended.”

In spite of the 27-year age gap and enormous power differential between the president and the former White House intern, Maher added:

“I think Monica Lewinsky is the one who should apologize to America. She’s the homewrecker. And if anybody really owes an apology, I think it’s her.”

Like Letterman, Maher was also affected by Lewinsky’s essay for Vanity Fair.

“I was moved by it. I gotta tell you, I literally felt guilty,” Maher told his HBO audience in 2014. “I remember doing a million Monica Lewinsky blow job jokes, and I kinda feel bad.”

Recalling the gist of her essay to his audience, Maher explained, “She says it out there, which is basically, ‘I’ve spent 20 years in infamous person prison, because what? I had an affair in my early 20s’…People have worse problems, but I am sympathetic to her.”

Since that public change of heart, Maher has seemingly remained in Lewinsky’s corner. Just last year, when Clinton claimed that his affair with Lewinsky had been a means to manage his anxiety, Maher called out the former president on Real Time.

“Can I, for one second, channel Monica Lewinsky?” said Maher, referencing the explanation Clinton gave in Hulu’s documentary about Hillary Clinton. “Just gotta say the blindness of a man saying that I had this affair with this person was to manage my anxieties—how does that make her feel? It’s a terrible thing to say…This to me was very callous. It’s like, ‘Is there a human being there?’”

Since 2014, Lewinsky has taken control of her narrative by publicly speaking about bullying and the harm it causes.

“We tend to look at [it] as a binary question; should we public shame or shouldn’t we?” Lewinsky told John Oliver in a 2019 interview. “I do think there’s a spectrum of behavior on which we can kind of judge as a society, is this where shaming is effective to change social behavior or is it damaging?”

Speaking about her own experience, she added, “I think at 24 years old it was really hard to hold on to a shred of dignity or self-esteem when you’re just the butt of so many jokes.”

During the interview, Oliver asked Lewinsky, quite simply, how she survived the ridicule.

“I don’t actually know,” Lewinsky responded. “It was an avalanche of pain and humiliation.”

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