David Fincher is one of the great stylistic directors of the last few decades. His films are generally very dark, with an almost sanitized industrial look to them. Like Silence of the Lambs before it, Se7en (1995) was extremely influential on the serial killer movies of the preceding decade. I would go so far as to say that Saw, and by extension, the rest of the torture porn genre wouldn't have existed without it.
Fight Club (1999) was also an extremely influential movie on the following decade. That movie, along with the matrix carved out a look and a style that movies would imitate for years to come. Dark, ruinous, city-scapes populated by meticulously groomed miscreants in expensive leather and sunglasses; Like robbing an empty mall at night and taking the most stylish and expensive items. While I don't think Fight Club holds up on a story level (stupid twist-ending, dumb philosophy that seemed invented by a twelve year old), this can't really be blamed on Fincher because it's based on a Chuck Palinuck book. However, it's the imagery of the movie that really stands out. It's probably one of the best movies to look to for a an example of turn of the century American cinema. Also, Brad Pitt and Edward Norton really excel in their roles despite the inherent ridiculousness of their situation.
Being someone who finished middle school around the same time that Fight Club came out, I can attest that it was one of the most popular high school movies to like, and in many ways, the themes he explores in those early movies really resonated with me. The turn of the century was a time of technological boom and financial excess with an undercurrent of existential dread. The internet was still new and scary, and watching his movies always remind me of those times.