Saturday Night Live has never shied away from controversial topics, especially when it comes to political scandals. So, of course, when the Clinton-Lewinsky scandal broke in 1998, SNL wasted no time casting Molly Shannon as Monica Lewinsky as one of their many recurring political impressions. What some people might not remember is Lewinsky stepping in to cameo as herself in a couple sketches, including Tim Meadows’ “The Ladies Man.” It turns out this was the one sketch Meadows didn’t want to do, and there’s one reason why he ended up going along with it.
Shortly after Lewinsky sat down for her 20/20 interview with Barbara Walters, where the former White House intern detailed her side of the situation, she started booking media spots. That included a cameo on SNL in the fall of 1999. Meadows, who was the longest running cast member at the time, recently told Matt Wilstein on The Last Laugh that despite participating in the sketches, he was originally against Lewinsky’s guest appearance:
We were told during the writers meeting that she was available for sketches that week, and so she would only be in a couple. And I think Lorne told us to write a Ladies Man, and I was against it, to be honest. She knows this, I met her, we talked about it. I was against it because I didn’t want to, I’m not a fan of the characters you make fun of are coming on and being themselves on the show.
SNL could be pretty brutal sometimes, and the series had made jokes about Monica Lewinsky being naive. The writers behind some of those famous sketches spread the love though, making just as much fun of Linda Tripp, Bill and Hillary Clinton and even Barbara Walters.
In some cases, what such situations could all come down to is whether or not these famous figures cope with their media scandals through humor, accepting the jokes that come with the territory. In her 1999 20/20 interview with Walters, Lewinsky was asked how she felt about all the jokes made at her expense on SNL and late-night talk shows. At the time, Lewinsky said she thought she had a very good sense of humor.
Tim Meadows seemed to agree, saying it was Lewinsky’s personality and reaction to her situation that convinced him to do “The Ladies Man” sketch with her:
I just felt like it was just a weird thing for us to be having her on. But then I met her. Those guys, Harper and Dennis, wrote the sketch. I was like, if you wanna do it, have fun, I’ll do whatever you want. But then when I met her, she was the sweetest person, and I thought, all the stuff that she’s been through, and she was an intern, and so when I met her it changed everything.
“The Ladies Man” Leon Phelps is arguably Meadow’s most well-known SNL character, one that probably wouldn’t fly in today’s cultural climate. The concept is that Leon hosts a call-in radio show where he gives (pretty terrible) dating advice, coining the catchphrase “Ooooh, it’s a lady” for whenever a woman was on the line. While the DMV actor revealed “The Ladies Man” was not originally supposed to be a recurring sketch, by the time Lewinsky made her appearance next to Leon, he had been giving poor dating advice for a couple years.
It makes sense that given the nature of the Bill Clinton scandal, the Saturday Night Live writers would have her and the Ladies Man giving advice about affairs with your co-workers and intimacy over the phone. Still, it’s a delicate subject, and I can see how Meadows would be against doing the sketch without conferring with Lewinsky. (Although I have to assume refusal to do the sketch would have landed him a trip to 17.)
I have to say, watching this sketch back over 20 years later, I find myself wincing at some of the lines they make Lewinsky say. I think it helps that Meadow’s Phelps is just as candid and even more self-deprecating when it comes to his own sexual escapades. From the looks of it, the Grown Ups actor seems like a very supportive presence for his guest during the sketch:
Lewinsky has since taken back her own narrative with her new podcast Reclaiming with Monica Lewinsky, and I would honestly love to hear her take on this Saturday Night Live appearance with 20+ years hindsight. In the meantime, classic episodes of SNL can be streamed with a Peacock subscription.
