Everybody mentioned the famous classics, so here's a few of my favorites (in no particular order):
"Nude House of Wacky People" (Nov. 15 1989) - Mike Myers shines as a Japanese TV exec presenting US-inspired sitcoms to a US audience. Only shown once, not on the SNL 1989 DVD, considered too racist. Look it up online. It's genious. "so funny; I have to laugh again."
"Sinatra Group" (Jan. 19 1991) - Even if you don't get the "McLaughlin Group" reference (another great skit starring Dana Carvey), you can't deny the talent of the players. Sting as Billy Idol, Jan Hooks as Sinead O'Conner, Chris Rock as Luther Campbell, Jackson & Myers as Steve & Edie, and of course Phil Hartman as the Chairman. Best line ever: "I got chunks of guys like you in my stool."
"Winston University" (March 17 1984) - Strangley prophetic in this age of for-profit universities. A colleges admissions counselor (Billy Crustal) shows some kids why higher education is so worth it. This skit reminds us of some of the forgotten stars of the show in the 80s (e.g., Robin Duke). Look for a young Julia Louis-Dreyfus among the students. "we will find you, and we will kill you..."
"Grumpy Old Man" (April 14 1990) - He's funnier than Carvey's Church Lady, and just like every old uncle you ever had. Looking back, some of my favoprite characters were from the Weekend Update spots. "
Life was a carnival! We entertained ourselves! We didn't need
moooovin' pitchurrrres. In my day, there was only one show in town -- it was called 'Stare at the sun!'"
"Stand Up and Win" (April 18 1992) - Before "Celebrity Jeopardy" we had this game show skit hosted by the real Jerry Seinfeld. The questions and answers were taken from Seinfeld stand up material, and the guests (Sandler, Schneider, Carvey) were all Seinfeld impersonators. A clever use of a host for a skit. "who are the ad wizards who came up with that one?"
"Matt Foley" (May 8 1993) - "
Well dad, why don't you just shut your big YAPPER?!" What more can I say?
"Adam Sandler's Halloween Costumes" (Oct. 26 1991) - Another Weekend Update spot. Only Adam Sandler could pull off an idea so stupidly simple and make it hilarious. Sure, Cajun Man and Opera Man were great, but this bests them both in its absurdity. "now gimmee some candy."
