1.
Clueless (1995). There is no film that screams 90's quite like this. From the clothing styles, to the catch phrases, this is THE quintessential film of the decade. So much so that Alicia Silverstone's supporting young cast in this movie wound up playing high school students in films for the next 10 years after this. Now, nearly 20 years later I still find myself wondering what phrases like "cake boy," "monet," and "betty" actually mean, but we can all agree that we are all better people for having heard our friends belt out "as if!" during awkward situations as teenagers.
2.
Scream (1996). There is no doubt that "Scream" singlehandedly rejuvenated the dying horror genre during the 90's. One of the first major motion pictures of its kind, "Scream" brought a self-aware almost parodical approach to the horror-slasher genre and brought back the nostalgic feel of past films such as "Halloween," "Nightmare on Elm Street," and "Friday the 13th." They also rolled out a very hip, good-looking (albeit a little old looking) cast that certainly added to the style of the movie. After "Scream," the copycats came in waves (I know What You Did Last Summer, Urban Legend, etc) but "Scream" will always be remembered for its lasting impression on slasher films.
3.
Pulp Fiction (1994). Perhaps director Quentin Tarantino's finest hour, "Pulp Ficton" may not have "1990's" written all over the plot, but this is a movie that EVERYONE was talking about upon its release, and a film that is still discussed at great length today. An amazing cast featuring John Travolta, Uma Thurman, Bruce Willis etc, help make this intertwining- style plot work to perfection.
4.
American Pie (1999). No doubt the "Breakfast Club" of the 90's generation. This film became synonymous with raunchy teen comedies and featured a soundtrack of late 90's classics as a perfect backdrop for the story. When you have a movie that teenagers can relate to, then you have struck gold and "American Pie" did just that. What the 90's had been missing with regards to the teen genre, this film more than made up for during the decades final year. Phrases from this movie are still being used by people 15 years later (MILF anyone).
Billy Madison (1995)/Happy Gilmore (1996). It would be a shame to include one of these films without the other so here I list them as a package deal. Adam Sandler came at us with two of the best comedies of the decade and people well into their 30's are still quoting these classics. The random quirkiness of "Billy Madison" certainly left a lasting impact and the over-the-top style of "Happy Gilmore" suddenly made everyone a fan of golf long before Tiger Woods entered our lives. Fans of Adam Sandler today, however, may be shocked to find out that at one point he was churning out amazing comedies.
6.
Mrs. Doubtfire (1993). One of the best all around films of the decade, "Mrs. Doubtfire" was an instant classic upon its release in 1993 and remains one of Robin Williams finest moments as an actor. This film works as a tremendous comedy, but also as a good-hearted story that deals with the difficult issue of divorce and the effect it has on both the parents and children. The final dinner scene is just pure gold as Williams' character has to continuously go back and forth from being Mrs. Doubtfire to himself to appease the different guests he is at the restaurant with.
7.
Dumb and Dumber (1994). Possibly the essential comedy of all time, let alone the 90's. Actors Jim Carrey and Jeff Daniels work perfectly together in this slapstick classic. A nice array of mid-90's alt rock, amazingly hilarious quotes and the backdrop of the beautiful Rocky Mountains helped make "Dumb and Dumber" the benchmark for all comedies that followed. And as far as a sequel goes..."So your tellin me there's a chance...YEAHHH!"
8.
The Crow (1994). The Crow is a very dark film, but is absolutely beautiful in its own right. Actor Brandon Lee played the tragic Eric Draven character to perfection and was unfortunately immortalized in the role as he was accidentally shot and killed during the making of the movie. "The Crow" makes this list because, it is not only an amazing film, but the soundtrack is pure 90's grunge rock. Stone Temple Pilots, The Cure, Pantera all help tell the tragic tale of the film and the cinematography and darkness of the picture certainly reminds you of the darker, more introspective rock music of the early 90's.
9.
Varsity Blues (1999). This would be MTV's version of the 1988 book "Friday Night Lights" which tells the true story of a Texas high school football team and the pressures that they face as young kids. "Varsity Blues" takes it in a more comedic direction and the cast make it work wonderfully. For many guys my age, this is exactly what you wanted your high school football life to look like. Intense games on the field, an entire town living and dying with every game and parties with hot chicks and pigs off the field. Oh and seriously what ever happened to James Van der Beek?
10.
Fear (1996). Possibly the biggest surprise on my list, but this film was a frequent view of mine during the mid-late 90's and encapsulates the decade as well as any movie made at that time. This movie may be a bit obscure especially considering the inclusion of Mark Wahlberg and Reese Witherspoon, but it is a great thriller/unintentional time period piece that should garnish more attention. Maybe it is the fact that it takes place in Seattle during the grunge era that really gives the movie its 90's feel, or possibly it is the inclusion of the two insanely popular songs by the band Bush (my goodness "Sixteen Stone" was a great album) but "Fear" will always be a tremendous representation of the 1990's.
Extremely honorable mentions: Independence Day, Can't Hardly Wait, Mighty Ducks 2, The Sandlot, Son-in-Law, Point Break, Terminator 2,American Beauty, Twister.