Scot Bertram

There are celebrity cameos on Saturday Night Live, and then there is the cameo that occurred on the show on May 8 of 1999, which may have been the most surprising of all. When a dark-haired woman appeared in the middle of a sketch about Bill Clinton’s activities after he left the White House, the audience engaged in subdued applause, as it seems they couldn’t figure out…is that really Monica Lewinsky?

In fact, it was, and Lewinsky dutifully read her lines, as if she was talking to Bill Clinton himself (played, as usual, by Darrell Hammond.) Lewinsky further appeared in a Ladies Man sketch, which teased her about her libidinous activities within the White House.

But was the decision to include Lewinsky a crass ratings play, or a wise use of a willing public figure? We discuss both sides on this week’s podcast, which also includes a discussion of the new cast members, Jimmy Fallon, Chris Parnell, and Horatio Sanz.

Of course, the show is once again dominated by Will Ferrell, although his presence is sporadic during the middle of the season as he is off working on other movie projects. Molly Shannon, Cheri Oteri, Ana Gasteyer, Tim Meadows and Chris Kattan are there to pick up the slack, buoyed by the new guys.

In picking hosts for the season, the show leaned into a number of young, up-and-coming actresses, each of which performed well. Gwyneth Paltrow, Jennifer Love-Hewitt, Sarah Michelle Gellar, Drew Barrymore, and Cameron Diaz all performed admirably, even though the quality of their episodes were sporadic. Conversely, shows hosted by male stars like Vince Vaughn, Bill Murray, and Brendan Fraser sagged.

Cast member Colin Quinn retained the Weekend Update desk for another season, this time beginning his desk pieces with a standing monologue, a convention which was quickly scrapped.

The best episode of the season belonged to host Ray Romano, who brought a number of his Everybody Loves Raymond writers along with him. It is his episode that had people saying “sweet sassy molassey” in the fall of 1998. Other sketch highlights for the season included Celebrity Jeopardy! rounding into shape and America getting a feel for Schweddy Balls.

We discuss all these topics and much more on this week’s episode of Wasn’t That Special. Please subscribe and join us for a trip through every year of SNL. And consider joining at the Executive Producer level, where you get a whole load of extra commentary and clips that will help you become an SNL expert.