Please note these are my ranking only of films I've seen. Any films you think should be on this list may be due to the fact I've yet to watch them. I welcome any recommendations of films which should be included.
1. Magnolia - Paul Thomas Anderson's masterpiece of misery and redemption. Brilliant in every way. Shame on the Academy!
2. American Beauty - Scathingly funny yet deeply profound. Worth all the praise it has received.
3. The Insider - Brilliantly acted and directed, and absolutely riveting. Russell Crowe was robbed.
4. The Green Mile - Frank Darabont follows up SHAWSHANK with another Oscar-worthy Stephen King prison drama adaptation. Masterful.
5. The Hurricane - Denzel Washington and director Norman Jewison deliver big-time in a genuinely compelling true story.
6. Election- Vastly overlooked, yet one of the best teen comedies of the 90s. Inspired and brilliantly directed.
7. Being John Malkovich - Totally original and prodigiously conceived. Another great comedy in 1999 from a first-time writer and director.
8. Toy Story 2 - Perhaps even better than the first. A completely ingenious animation and clever story from Pixar.
9. Star Wars Episode One - The Phantom Menace - Lucas at the helm once again making the cinematic experience awe-inspiring for another generation.
10. The Talented Mr. Ripley - Hitchcock would be proud of his legacy which proves it's the themes that make thrillers great and not just technique.
Honorable Mention - All About My Mother, Analyze This, The Big Kahuna, The Boondock Saints, Bringing Out the Dead, The Cider House Rules, Cookie's Fortune, The End of the Affair, Eyes Wide Shut, Fight Club, For the Love of the Game, Galaxy Quest, Go, Hilary and Jackie, An Ideal Husband, The Iron Giant, Liberty Heights, The Matrix, The Mission, Notting Hill, Payback, Runaway Bride, Running Out of Time, The Sixth Sense, Snow Falling on Cedars, Sweet and Lowdown, Three Kings, A Walk on the Moon
Noteworthy films I haven't seen yet - American Movie, Drop Dead Gorgeous, Existo, Fantasia 2000, Felicia's Journey, The Five Senses, Gigantics, Girl Interrupted, Henry Hill, Himalaya, It All Starts Today, Kadosh, Mansfield Park, Mr. Death, My Best Friend, Not One Less, October Sky, The Road Home, Shower, Spring Forward, The Straight Story, Sunshine, Tarzan, Titus, Topsy-Turvy, Trick, Twin Falls idaho, Voyages, The War Zone
Films I think are overrated: Arlington Road, The Blair Witch Project, Boys Don't Cry, Dogma, Ghost Dog: The Way of the Samurai, In Dreams, Limbo, The Limey, Office Space, Sleepy Hollow, South Park: Bigger Longer & Uncut, Stir of Echoes, The Virgin Suicides, The Winslow Boy