As the Associated Press reported at the time, Monica Lewinsky’s “Saturday Night Live” cameo took place in May 1999, just months after Bill Clinton was acquitted by the Senate. Her appearance was central to the plot an installation of the long-running “SNL” sketch “The Ladies’ Man,” which routinely featured cast member Tim Meadows dispensing tongue-in-cheek advice to various people who called into a hotline for his dating expertise.
The sketch, which featured Lewinsky as a guest, used her cameo as a vehicle to rib Lewinsky for participating in a sexual relationship with then-President Clinton, with references to the Clinton scandal — ones which, as Decider noted in its 2021 critique of how the controversy was handled by “SNL” at the time, seemed steeped in “part serendipity” and “part meanness.”
While Lewinsky seemed to take the whole thing in stride with (albeit scripted) earnestness in her responses — after a caller asks her whether she has had phone sex, she says she has “with one guy,” but “his name doesn’t really matter,” Meadows quips in with “why don’t we just call him William Howard Taft?” — parts of the skit are uncomfortable with the distance of age. And the most glaring offense in this case actually has little to do with Lewinsky — and everything to do with another point person in the Clinton scandal.