1999 is pretty good. Among the best. But I actually think 2000 is better - not the top 3 maybe, but the next several at least in the top 12 to 15. Maybe not as deep overall though.
Best of 2000:
Gladiator
Traffic
O' Brother, Where Art Thou?
That's a big 3. Gladiator was a big big film winning Best Picture and that puts it way ahead of 1999 (American Beauty) in that consideration at least. Traffic was groundbreaking - Soderbergh 2nd huge film of the year and the one he won best director for. those 2 might not be as mind bending as The Matrix and Fight Club but they are better films overall. And more repeat watchable for me. And "O' Brother" is more cult worthy than even Office Space and one of the Coen Brothers best.
Crouching Tiger, Hidden Dragon - 1999 does not have a foreign film to rival this. It's a work of art.
I actually loathe 4-6 on the 1999 list - Magnolia tries too hard, Talented Mr. Ripley is boring, Election was blah.
These 2000 films are all better:
Cast Away - a big tom Hanks vehicle
Remember The Titans - feel good movie, great sports movie and quotable
The Patriot - decent period piece, historically inaccurate but America!!!
Almost Famous - very well done critically acclaimed Cameron Crowe pic
Erin Brokovich - the other Soderbergh pic that year did really well and won Roberts an Oscar
and as for horror- Frequency was wayyyy better than Blair Witch (over hyped garbage).
Meet The Parents - maybe not quite the level of American Pie but a solid comedy film franchise for Stiller and co.
Requiem For a Dream - is waayyy freakier and more disturbing than Eyes Wide Shut (which was tiresome and monotonous and I'm a huge Kubrick fan).
U-571 is better than Three Kings for a war entry.
Miss Congeniality - might not be Julia Roberts but it's a funner movie than Notting Hill for romantic comedy.
High Fidelity - another cult classic
Lots more - although I admit it falls off a bit here:
Unbreakable
X-Men
Mission: Impossible 2
Chocolat
Dr. Seuss' How the Grinch Stole Christmas
Finding Forrester
Dinosaur
Thirteen Days
Bounce
Proof of Life
Malena
The Perfect Storm
28 Days
Shaft
Pay It Forward
Legend of Bagger Vance
Hollow Man
Coyote Ugly
Red Planet
What Women Want
Space Cowboys
Anyway - to each his own - but I'll take 2000 over 1999 even though 1999 top 3 are probably more impactful from a pop culture point of view at least.