40. Election, 1999
Dir: Alexander Payne
Cast: Matthew Broderick, Reese Witherspoon
Alexander Payne's funniest film, by far, Election is a biting satire on politics set in a high school where a couple of teens are running for HS president. What's even better is the passive-aggressive rivalry between Matthew Broderick and Reese Witherspoon's characters. A rivalry that lasts all the way up til the end of the movie. Election really demonstrated Payne's potential as a director when he made this '90s classic.
39. Beauty and the Beast, 1991
Dir: Gary Trousdale, Kirk Wise
Visually arresting, a wonderful (if not, somewhat odd) love story and it's clearly one of Disney's best 2-D animated movies. That is, at least of the latter half of the 20th century. This movie was even nominated for Best Picture which is impressive considering all the impressive efforts made by Pixar in this decade and all they can get is Best Animated Picture (which wasn't around in 1991, as you may know).
38. 12 Monkeys, 1995
Dir: Terry Gilliam
Cast: Bruce Willis, Brad Pitt
Easily Terry Gilliam's most commercially films and proof that he can make movies for the people. This could also be considered his most accessible film and it's interesting to see Gilliam working in a more controlled nature. I use the term "controlled" loosely as he still leaves us with a film that's quite a head-scratcher. Also impressive is how he worked with Bruce Willis to give him one of his most vulnerable roles where he's not just kicking ass and taking names all the time. Brad Pitt also gives a wonderful performance.
37. Out of Sight, 1998
Dir: Steven Soderbergh
Cast: George Clooney, Jennifer Lopez
The movie that broke Steven Soderbergh out into the maintstream; Out of Sight also turned George Clooney and Jennifer Lopez as true movie stars. Of course, one has continued to become a success both financially and critically (winning an Oscar in the process) and the other has managed to squander her career slowly throughout the next decade. I'll let you guess which one is which... even though I already used some key pronouns that should give it away.
36. My Own Private Idaho, 1991
Dir: Gus Van Sant
Cast: Keanu Reeves, River Phoenix
Gus Van Sant is usually hit-or-miss for me, but when he hits... wow, I can be his biggest fan. Sure he's made some films that I've hated, but My Own Private Idaho is not one of them. A movie about two gay, male prostitutes searching... trying to find a home. River Phoenix really shows just how talented he is and what a shame it was when he passed. This is one of the definitive road movies of the '90s.
35. Shawshank Redemption, 1994
Dir: Frank Darabont
Cast: Tim Robbins, Morgan Freeman
Before Frank Darabont made The Green Mile, he made this other prison drama classic based off a Stephen King story. What's striking about this story is just how well it translates onto the screen as well as how convincing and wonderful Tim Robbins and Morgan Freeman's performances are. But the real treat is watching how this story unfolds. Obviously this movie has stricken a chord with people since its 1994 release as it's ranked #1 on imdb. Perhaps that gives the film an unfair overhyped status, but it didn't have that when I saw it the first time and I loved it too.
34. The People vs. Larry Flynt, 1996
Dir: Milos Forman
Cast: Woody Harrelson, Edward Norton
I've seen this movie quite a few times and, I don't know why, but I love both of Forman's biopics: the one of Larry Flynt and the one of Andy Kaufman. What makes this one so much better is the fact that... well... Larry Flynt's life story is that much more interesting. But, more than that, this film really is masterfully made by one of the cinema's great masters.
33. The Player, 1992
Dir: Robert Altman
Cast: Tim Robbins
Starting off with a very long, 8-minute, one-take shot introducing us to, pretty much, all the characters that we are to later see in the movie... The Player is a wonderful sardonic take on Hollywood. Starring a wonderful ensemble cast, this almost feels like a Robert Altman revenge tale. Robert Altman, of course, was one of the greatest directors of the 1970s, but in the 1980s his career took a serious hit. He came back in a big way, however, with The Player and it happens to be about the very same town that turned on him during the '80s. The film could be considered bitter... if it weren't so damn right.
32. Leaving Las Vegas, 1995
Dir: Mike Figgis
Cast: Nicolas Cage, Elisabeth Shue
Mike Figgi's poetic, beautiful, heartbreaking film (by the way, I'm doing 100 of these movies, if I repeat some of these adjectives then I'm SORRY, ok??) Leaving Las Vegas features Nicolas Cage's best performance ever. His performance is so raw and sad that it shocking how he often stars in all these stupid action movies that almost seem like a self-parody. Either way, this movie about a man's never-ending bout with alcoholism is very sad, but not in a manipulative way. It's a great film, but you might not want to watch it if you're in a really happy mood because it's quite the downer.
31. Dazed and Confused, 1993
Dir: Richard Linklater
Cast: Jason London, Matthew McConaughey
Virtually ignored when it was released, Dazed and Confused has since become a cult success. But, honestly, this isn't just a film for druggie teens and college students. This is, in many ways, an amazing film. Filled with so many interesting characters just hanging out and having a good time. If you expect the usual high school comedy, then go see American Pie. This is a honest and mature film about growing up and trying to make high school a time where the memories will never die. This also features a great performance by Matthew McConaughey as 20-something guy you like to hang out with, but you never want to grow up and be like him. Dazed and Confused contains so many great lines, great scenes, and great acting. Many of these actors have gone on to have mainstream success and indie success from Ben Affleck, McConaughey, Parker Posey, and Adam Goldberg. What's funny is that Adam Goldberg essentially plays the same character that he's since gone on to play in many subsequent movies and tv shows.