Air Date: Feb. 22, 1992
Starring: Mike Myers, Madonna, Roseanne Barr

Over the years, we've witnessed countless dudes performing in drag on SNL for the sake of bringing the laughs, but it has to be said that there's no SNL lady-boy more memorable than Linda Richman. Mike Myers' middle-aged, exaggeratedly Jewish character (modeled after his own mother-in-law) hosts a call-in talk show and is known primarily for three things: Her intense Long Island accent, her crazy hair and jewelry, and her huge obsession with Barbara Streisand.

In the series' most popular episode, Madonna and Roseanne Barr appear on "Coffee Talk" as Linda's best friend and her gassy mother. Madonna, as the friend, starts talking shit about Madonna, calling her a tramp and saying she's a shitty role model for Jewish girls, while Roseanne just does her thing in the background. Just as the sketch is about to end, however, and the three are signing off, out pops, who else, Barbara Streisand from backstage in a surprise appearance that, reportedly, not even the actors had anticipated.

Yeah, SNL was cool like that. Fortunately, the three were able to keep it together and remain in character, unlike Jimmy Fallon during pretty much all of his sketches.