100. Pleasantville - This quirky little dramaedy didn't get half the recognition it deserved for prefectly balancing the sweetness and retro of the world of Pleasantville, and the vibrant and dramatic of the world it became. Pleasantville helped launch the careers of Tobey Maguire and Reese Witherspoon, and proved that fine actors such as Joan Allen, Jeff Daniels, and William H. Macy could expand their acting abilities. A fine piece to watch.99. Jerry Maguire - SHOW ME THE MONEY! Cuba Gooding Jr. used to be a great actor, and in this Academy Award winning performance he brought enthusiasm and intensity to the role of a washed up football player, perfectly parallelling the downward spiral of Tom Cruise's Jerry. Cameron Crowe would top this effort a couple of years later with the incredible Almost Famous, but his winning combination of humor, romance, and sports showed how talented of a screenwrite he really is, and why we still feel completed by Renee Zellweger.
98. The Simpson's Movie - Still one of the more recent shocks, The Simpson's Movie may not have gotten a well-deserved Animated Feature nod, it still was one of the best in my opinion. It isn't easy to take the most successful television series of all time and create a movie that manages to still be original, funny, and keep us wanting more, but this film did it. Really it just felt like an extended version of a really good episode...and that is a high complement.
97. The Matrix - While its two successors may have fizzled out, fans of the series will always have this enduring sci-fi masterpiece. Avatar may have been a visual treat, but The Matrix revolutionized the game long before Jim even got his act together. What The Matrix did was give sci-fi geeks the break they had been looking for, combining the revolutionary technology at the turn of the century with a classic graphic novel appeal that had them cheering and wanting more.
96. The Breakfast Club - Probably one of the most influential and popular movies of the last quarter century, The Breakfast Club expressed the sentiment and trouble that teenagers feel unlike any other of the classic John Hughes 80's movies. The stereotypes that were represented, preppy, jock, geek, badass, and weird may have been overplayed, but it is because of The Breakfast Club that we have so many cliches, and why we have an entire genre of teen angst movies. In some ways it was groundbreaking, in other ways it simply said all the things we wish we could have said when we were that age.
95. X2: X-Men United - My favorite superhero franchise besides Christopher Nolan's Batman, but for those of us who truly love comic book movies, the second of the X-Men series was absolutely heaven. It combined all of the cool special effects and awesome powers of our favorite heroes and villians, but also combined a great psychological thriller that was dark, thrilling, emotional and superbly executed. While the third movie wouldn't hold up, this middle child turned out to be one of the best.
94. Out of Sight - In my opinion, this was one of the most underrated movies of the last 25 years. It had pitch perfect performances from George Clooney and Jennifer Lopez, and combined an excellent blend of romance, action, and heist action to a make a little movie that was tight, thrilling, and exciting to watch. Steven Soderbergh may have gotten more recognition f
or Erin Brochovich and Traffic (well-deserved, I might add), but many of us will soon not forget this earlier classic.93. Far From Heaven - 2002 was a great year for great movies, and one of the little gems that failed to gain much traction was this beautifully haunting story of a 1950's housewife that discovers that her husband is gay and potentially has a relationship with a sympathetic black man. This movie was impeccably acted, and Julianne Moore was robbed of a well-deserved Oscar. If you want a movie about change and the strength we find when our world is turned upside down, then this is your movie, and you can't go wrong.
92. Eternal Sunshine of the Spotless of Mind - This quirky little comedy proved that Jim Carrey could act, that Kate Winslet could branch out of her comfort zone, and that even the strangest of plot lines could capture your mind and your heart in a rare feat. Michael Gondry has found a knack for creating these types of movies, and although some of his works have been just a little bit over the top, but in this instance, with this incredible cast, he hit the nail on the head.
91. South Park: Bigger, Longer & Uncut - The crudest, loudest, and most political incorrect movie ever made, and one of the best. Like The Simpson's Movie did later, South Park: Bigger, Longer, & Uncut combined the perfect elements of a great episode of South Park, and made it really work even in a much longer form. What was so great about the show/movie was how it was never afraid to take risks. While many were offended throughout its running (including myself in many parts), I can't help but love its tenacity and boldness.
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