89. The American President - This is a personal fave, and might surprise some, but back in 1995, Carl Reiner perfectly combined a mix of politicals and passion with a little humor with a two-fold story about two important pieces of legislation and the effects of a politician dating a lobbyist. If it sounds like a lot it is, and yet it is a pitch perfect blend that never exceeds its welcome and always mananges to fascinate and charm. It doesn't hurt that the incredible talents of Michael Douglas, Annette Benning, Michael J. Fox, Martin Sheen, Anna Deveare Smith, and Samantha Mathis shine.
88. The Insider - Michael Mann was never able to top his 1995 classic Heat (as you will see much later on), but he got pretty damn close with this 1999 whistleblowing thriller with the great talents of Russell Crowe, Al Pacino, and Christopher Plummer, and an incredible story. When Mann hits his target on thrillers, he has an incredible knack for combining a great storyline with choppy, yet effective editing that creates a gritty, surreal environment that is hard to match.
87. Dreamgirls - While many dissed this glitzy, pop musical, I can honestly say that this was one of the best times I have ever had in a movie theater. Too many musicals tried to copy the success of Chicago by trying to make the story too gritty or focusing too much on making it stylish, and forgetting to make it fun. Not to say that Dreamgirls was pop heaven, stuffed with the style and attitude of the 1960's, but still managed to make a toe-tapping musical that had great performances, most notably Jennifer Hudson, and had the crowds singing long after they left the theater.
86. Pirates of the Caribbean: The Curse of the Black Pearl - While its sequels never really amounted to much more than popcorn trash, this surprise little hit was one of the most fun and entertaining movies that was released in the last quarter century, and it put Johnny Depp on the map. His performance as Capt. Jack Sparrow will go down as one of the greatest movie characters of all time, and it is my belief that he was closer to winning an Oscar than most people think. But overall, the magic, style, and the popcorn perfection of this movie made it the perfect summer outing.
85. Up - Pixar will appear a lot on this list (sorry for giving up too many hints), but its most recent entry cannot be so quickly forgotten. Not only was it the second animated movie to ever receive a Best Picture nomination, but more importantly, it proved that Pixar is the best studio in Hollywood. It is the only studio that continually, and annually releases not just popular movies, but incredible movies with incredible stories. And the story of the unlikely pair of a old man and a young scout on a whirlwind adventure was no exception.
84. Election - Alexander Payne has a knack for the quirky, and in 1999, he hit his stride with this pitch perfect comedy about the brutality of high school, seen through the lens of school elections. The relationships that were developed between students, teachers, were so realistic and so bitter, I think we all felt like we were back in high school. It perfectly captured the bitterness and cynicism of high school, and had some great performances, particularly the wonderful Reese Witherspoon.
83. Dazed and Confused - If Election captured the bitterness of high school, then Dazed and Confused captured what could be so great about high school. Of course if all I did was smoked pot and looked like I was 25 in high school, I probably would have been happy too. What Dazed and Confused did was provide a new generation a look back at the culture and attitudes of those at the Bicentennial. Furthermore, while Cheech and Chong were anything but subtle, D & C took the pot culture to a new level, allowing for characterizations, subtletly, and humor.
82. There's Something About Mary - I love great comedy films as well, I mean who doesn’t like to laugh? This one is definitely in that category, and will leave you laughing long after it’s over. Cameron Diaz was a revelation in this movie, and it was the only movie, with the exception of Crash that Matt Dillon did that was worth anything in the last twenty five years. This one is raunchy, yet has a lot of heart, and is definitely worth the rent.
81. Chicago - When Rob Marshall directed Nine, he tried so hard to make it Chicago, and it simply couldn't live up to its predecessor. Chicago was stylish, sexy, had great music, great performances from Queen Latifah, Renee Zellweger, Catherine Zeta-Jones, John C. Reilly, and Richard Gere, and helped relaunch the movie musical. Just when we thought that all hope for musicals was gone, Marshall, and this amazing team helped us believe in their everlasting spirit, and all that jazz.