4. Wayne's World: Madonna Fantasy
Original Airdate: May 11th, 1991
"It was terrifying," Mike Myers has said of kissing Madonna. And no wonder: In 1991, there was no more intimidating star than the just-banned-from-MTV Material Girl. Her fantasy rendezvous with Wayne and Garth was probably SNL's most perfect pop culture convergence ever: One of the most famous people on earth, writhing in the black-and-white world of "Justify My Love," the most controversial video of all time, speaking in the dopey slang ("No way!" "Way!") of the most popular recurring characters since the Blues Brothers. And we were only approaching Waynemania, which would peak in 1992 with their feature film. During shooting, Myers and Dana Carvey had a personal falling-out, and were never quite able to re-capture the magic – though that didn't stop Lorne Michaels from producing a sequel or doing the sketch seven more times.