Magnolia introduced me to P.T. Anderson, and I've been a devoted fan ever since. The performances are exceptional all around (easily my favorite Tom Cruise performance by the way), each character is fully developed by the end, and there's so much going on throughout the film to both entertain and provoke thought. It's also beautifully shot and carefully put together, with scenes that embed themselves in your head long after it ends.
Bowfinger: Do you have any experience in motion pictures?
Jiff: Uh, well, yeah, quite a bit, actually, I have quite a bit of experience. I'm an active, uh, renter at Blockbuster, and I, um, attend the filmed cinema, uh, as much as possible, weekly, bi-weekly, inter-week-... intermediately.
Bowfinger: Would you be willing to cut your hair?
Jiff: [sighs] Oh, yes, but, uh, it's usually better if someone else does it. I've had a few... accidents.
Top films listed in the order I like them, though repeat viewings could potentially rearrange said order. And of course the order could be further altered once I watch the "Unwatched contenders".
Runners-up and Unwatched contenders listed alphabetically.
If you'd asked my 1999 self...
2. American Beauty
3. Fight Club
5. Man on the Moon
6. Office Space
7. Eyes Wide Shut
8. The Sixth Sense
10. South Park: Bigger Longer and Uncut
12. Sleepy Hollow
13. The Matrix
By 1998, my taste had pretty well solidified. Which means the films listed above earned new places after I experienced the rest of the films on this list, none of which were experienced by me during 1999. I've included the above list just for the sake of reference and so it fits in with the annual lists made before it.