#5 - A Simple Plan
This film features what I consider to be Billy Bob Thornton's best performance (although I have not seen Sling Blade). A dark disturbing drama from Sam Raimi (one of his best films) that illustrates how money can ruin relationships. It includes two great staring turns by Bill Paxton and Bridget Fonda. This is a tense movie that unravels brilliantly in front of the viewer.
#4 - Sneakers
Robert Redford and Sidney Poitier lead an all-star cast including Mary McDonnell, Ben Kingsley, Dan Akyroyd and a just-before-death River Phoenix. The entire movie deals with espionage, code breaking and various levels of spy stealthdom. You will not be bored at all in this movie. In my opinion this is Redford's most memorable role. NO MORE SECRETS
#3 - Dark City
This movie is just plain awesome. From The Strangers (darkly-dressed weird dudes with funky names like Mr. Hand and Mr. Wall) and their building changing abilities to a pre-24 Keifer Sutherland and his creepy stammering way of speaking, this movie is the type of oddball futuristic science fiction film that appeals to me. It's obvious that The Matrix and Inception borrowed some ideas from this groundbreaking 1998 film.
#2 - Rounders
The movie that single handedly launched the poker boom in the USA. Matt Damon and Edward Norton give great realistic performances and John Malcovich is in top form as Teddy KGB. For guys who enjoy playing some cards, this is a top five all-time classic. It totally deserves to be in the IMDB Top 250.
#1 - The Game
David Fincher. Michael Douglas. Sean Penn. Perfect casting and a totally original and mind-bending plot make this one of my favorite films of all-time. The audience is in for a wild ride from start to finish. Because of the excellent twists and turns of the plot, this movie is best during the initial viewing but I still find myself putting down the remote every time I come across it on cable. If you haven't seen The Game, do yourself a favor and go rent it tonight.
Honorable Mention goes to The Sandlot, Sweeney Todd, Bill and Ted's Excellent Adventure and of course Ghostbusters II which all deserve to be in the top 250 on IMDB.
I'm sure I'm missing some more obvious ones that others can chime in on. Some that deserve to be removed from the Top 250 (in my opinion) are: The Green Mile, Donnie Darko, Ed Wood and No Country For Old Men.