18. Rushmore (1998)
Arguably the best film that Wes Anderson has made yet. Rushmore blends all of the signatures of his work in such a way that you can't help but enjoy the film even if you dislike Anderson's style. The influence of J.D. Salinger is very evident with Jason Schwartzman's Max character having a Holden Caulfield way about him. Another factor that makes Rushmore great is the casting of Bill Murray. It has been said that a great director is also a great casting agent and never before has Anderson been so spot on with his choice of actor. The story is typically quirky and humorous but the way that Anderson uses his characters to draw all of the humor to the forefront of the film while still keeping their humanity intact is truly a wonder.
17. The Big Lebowski (1998)
Surely the Coen Brothers' funniest film. The Big Lebowski has become extremely iconic in the years since its release and it's not hard to see why. Jeff Bridges' insanely quotable performance as Jeff "The Dude" Lebowski is one of the greatest comedic performances ever given and really displays the full range that Bridges can bring as an actor. John Goodman and Steve Buschemi are also huge scene stealers as well by helping build the sense of the characters that inhabit the film. The almost parody based narrative is also one of the best screenplays the Coens have ever written. The way they are able to weave each intersecting plot together while simultaneously deepening the plot is really brilliant. The Big Lebowski is almost a direct parody of Howard Hawk's, Raymond Chandler based, The Big Sleep but it walks the line between homage and originality so well that it perfectly comes across as its own movie.