The Simpsons has managed to book plenty of impressive guest stars over the years, but who are the three characters that comedian Sarah Silverman played in her four appearances on the series? Since its early seasons, The Simpsons has been able to wrangle some pretty amazing guest stars for one-off appearances. By the time the show was in its third year, the likes of Michael Jackson, Danny DeVito, and Dustin Hoffman had all lent their voices to characters on The Simpsons, with none of these sizable stars even playing themselves, despite their fame.
Since then, the show has fallen out of critical favor and, in recent years, has relied more and more on Simpsons guest stars playing themselves. However, the series still offers some choice cameo roles from time to time and invests in a guest star’s appearance by providing them with an original character. What is less typical, however, is the same guest star appearing as both themselves and numerous original characters on the long-running animated sitcom.
However, that is exactly what Sarah Silverman has managed in her four guest appearances on The Simpsons. The veteran comedian has shown up on The Simpsons four times, playing two original characters and herself in these appearances. First off, she appeared in season 21 and cropped up again in season 24 as one of Bart Simpson’s recurring girlfriends, Nikki McKenna. Then she had a cameo as herself in "Clown In The Dumps" (season 26, episode 1), followed by a final role as Lisa’s murderous imaginary friend Rachel in the best segment from "Treehouse of Horror XXVII" (season 28, episode 4).
Silverman’s first appearance was one of the show's numerous outings that pair Bart off with a short-lived love interest, in this case, the indecisive Nikki. The episode received mixed reviews but Silverman’s character was well-liked, so much so that she reappeared in a later outing wherein Bart revisited all of his exes to find out where he kept going wrong romantically. That momentary cameo was a brief role for Silverman, but her next appearance on The Simpsons came in a better-received outing. Despite Krusty’s character starring in some of The Simpsons’ most hated episodes, the 2014 outing where he said goodbye to his father was well-liked by critics and fans alike.
The episode’s reception was elevated by a stellar couch gag from animator Don Hertzfeldt, but Silverman’s role was a minor and one-note cameo with little connection to the plot. Luckily, her appearance in "Treehouse of Horror XXVII"'s “BFF RIP” more than made up for this. In this underrated segment from the show’s annual Halloween special, Silverman plays the vengeful ghost of Lisa’s imaginary friend, abandoned in childhood and now looking for brutal revenge on her creator. It is a gruesome, funny, and unusually inspired segment that proves The Simpsons can still create effective Halloween specials once the Treehouse of Horrors episodes return to their origins and stop trying to parody every passing pop culture fad. Unfortunately, this segment was one of the last original stories attempted by the Halloween outings of The Simpsons, which has since reverted to forgettable movie parodies.