I don't know if it's just that I was in my 20's and free as a bird, but I loved the 1990's. They kicked the 80's and 00's ass as far as popular culture is concerned. Music, clothing, TV and finally movies seemed to be extremely creative and fresh. Remember when the Breeders, Dinosaur Jr., Beck, Meat Puppets, Son Volt, Flaming Lips were all played on popular radio and MTV? Many of their "hits" were consumed by the masses and helped contribute to the soundtrack of the time.
When it comes to movies from the 1990's I really like Joe Holleman's take in the PD. His top 10 are: Pulp Fiction, L.A. Confidential, Fight Club, Shawshank Redemption, Fargo, Unforgiven, The Truman Show, Saving Private Ryan, Silence Of The Lambs and Goodfellas.
If a Quintin Tarantino movie is not at least in your top 3, I'll dismiss all other opinions. Mr. Holleman really seems to get it right. Although, I've never seen the Truman Show. Even his best actress (Frances McDermott) and most overrated movie (Dances with Wolves) is right on. And although the Big Labowski is a geat choice for best comedy, I've always thought Office Space is underrated with the pundit crowd. To me it's as representative of the 90's as Big Labowski.
My only complaint? Where is Rushmore?