I haven't seen 2007 mentioned yet. It's more recent than a lot of these suggestions but there were some incredible movies released then. The top 3, to me, are about as good as any top 3 from another year that I've seen: No Country for Old Men There Will Be Blood The Assassination of Jesse James by the Coward Robert Ford Gone Baby Gone Zodiac American Gangster Juno Eastern Promises Superbad Mr Brooks Into the Wild The Bourne Ultimatum 300 3:10 to Yuma Charlie Wilson's War
¯\_(ツ)_/¯ I just remembered posting it 'a while back' and searched for it. I'm fascinated with social trends and zeitgeist changes. Movies are a big part of that in the American culture. Thread has good existing info, no need to recreate.
Put some respeck on 1998!!! Saving Private Ryan The Truman Show The Big Lebowski American History X Blade Fallen The Thin Red Line There's Something About Mary Lock, Stock and Two Smoking Barrels Enemy of the State Wild Things You've Got Mail Fear and Loathing in Las Vegas Rushmore The Waterboy Rush Hour The Man in the Iron Mask Meet Joe Black Out of Sight Pi A Night at the Roxbury Rounders Half Baked He Got Game A Simple Plan The Negotiator Doctor Dolittle U.S. Marshals The Players Club Snake Eyes Belly How Stella Got Her Groove Back Bulworth Why Do Fools Fall in Love Ernest in the Army