50. Chasing Amy, 1997
Dir: Kevin Smith
Cast: Ben Affleck, Jason Lee
By and large, this is still Kevin Smith's finest film. I can say so much about Chasing Amy, about the characters' motivations, about how smart and witty the dialogue is, about how this movie can go from the low-brow sex jokes to very emotionally raw scenes within minutes from each other and it all completely works. This movie works on so many levels and it's fun to watch and appreciate a movie by Kevin Smith at his best.
49. Metropolitan, 1990
Dir: Whit Stillman
Cast: Carolyn Farina, Edward Clements
This movie, like a fine wine, just ages better over time. With Metropolitan, Whit Stillman really set the tone for comedies featuring really intelligent, yet disillusioned characters in their early-to-mid '20s... comedies you'd see a lot more of in the '90s thanks to the movie. They talk about Jane Austen books, socialism/communism, and judge you based on what type of overcoat you wear, or whether or not you take the taxi or a bus home. One of the best indie movies of the '90s, another film I can watch over and over again and enjoy it for different reasons.
48. The Truman Show, 1998
Dir: Peter Weir
Cast: Jim Carrey, Laura Linney
Jim Carrey's first dramatic role and boy what a great movie this is. Peter Weir, one of Australia's finest directors, made a brilliant film about a man whose life has unknowingly been broadcasted on television for over 30 years. Jim Carrey is flawless in this movie and so is Laura Linney who is a very underrated actress.
47. Leon: The Professional: 1994
Dir: Luc Besson
Cast: Jean Reno, Natalie Portman
Near-perfectly crafted film by Luc Besson, easily the best movie he has made and that is strange because of how effortless this movie feels. There's plenty of action in this movie to satisfy those kinds of fans, but it's also a wonderful drama about a hit man forced to take care of a 12-year-old girl whose parents were recently killed. This is unlike any action movie in '90s: one for action movie fans and art-house fans. That's probably why it's ranked #34 in imdb's top 250.
46. Total Recall, 1990
Dir: Paul Verhoeven
Cast: Arnold Schwarznegger, Sharon Stone
Setting the bar for sci-fi action thrillers to come in the future, Total Recall is a fantastic, violent movie with great scene after great scene. This is very much a Paul Verhoeven movie in its great visual effects, the aforementioned violence, as well as the way he injects his twisted tongue-in-cheek humor in some of the most intense scenes.
45. Magnolia, 1999
Dir: Paul Thomas Anderson
Cast: Tom Cruise, Phillip Seymour Hoffman
It's hard to believe that Paul Thomas Anderson was twenty-nine when he created this movie, but it's true. By Magnolia, PT Anderson had already perfected his craft and this movie is one of most expertly crafted films of the '90s. Top on some great, intensely emotional scenes with a third act that starts with a strange twist and you have yourself a wonderful movie. The movie sort of loses its edge with repeated viewings, but that only stops it from becoming one of the top 5 best movies of the '90s.
44. Jackie Brown, 1997
Dir: Quentin Tarantino
Cast: Pam Grier, Samuel L. Jackson
I never understood why fans of Tarantino regard this as one of his lesser works when it most definitely is not. In fact, Jackie Brown is still Tarantino at his most mature, most layered, and it contains some very surprisingly tender scenes between Pam Grier and Robert Forster that really makes this movie great.
43. Casino, 1995
Dir: Martin Scorsese
Cast: Robert Deniro, Joe Pesci
I know it's weird to say, especially since this movie is at #43 on my list, but this Scorsese on autopilot. Martin Scorsese, at this point, has become such a master at this type of movie that when it was released, it really didn't come as a surprise to many people. I don't know what people expected from Scorsese but after you make Taxi-Driver, Raging Bull, and Goodfellas it's hard to continually top yourself. Truth be told, however, this is the perfect companion piece to Goodfellas. It's just as wonderfully directed and crafted as Goodfellas, but it doesn't have some of the timeless, classic scenes that Goodfellas has. Also, Joe Pesci's character in this movie is not very different than his character in Goodfellas. But, again, Goodfellas is an all-time classic and this is a very great companion piece to that movie. Individually, it's great, compared to other Scorsese movies, it's business as usual. But the usual business is a great movie... see how it works? It'd be unusual business if it was a bad film about this subject, but that's not the case at all. Also should be mentioned that Sharon Stone almost steals the show from Deniro and Pesci in this movie.
42. Groundhog Day, 1993
Dir: Harold Ramis
Cast: Bill Murray, Andie Macdowell
Like Wayne's World, Swingers, and There's Something About Mary, Groundhog Day is another wonderful comedy that can be watched over and over. Which is ironic in a movie like this since Phil Connors lives the same day over and over in this movie. While this is a film that's primarily for the laughs, this movie also has a rather deep message about mortality... perhaps not that deep, but it's still there. Phil Connors living the same day everyday ultimately drives him to suicide... but he can't commit suicide, he has to learn to give up his cynical viewpoint of the world and impress its finer points.
41. The Big Lebowski, 1998
Dir: The Coen Brothers
Cast: Jeff Bridges, John Goodman
It's hard to add much to this movie as it has been talked about repeatedly since its gained a cult following. It's funny how the Coens followed this up to Fargo (which is so meticulous in its plot) because this movie does not care about its plot. I mean, yeah, there is a plot here somewhere, but... whatever dude. Let's go bowling. I don't know how this movie works so well, but it does. It's got the Coen Brothers magic sprinkled onto it and that's why it's still being watched (repeatedly) by people today. Nothing about it ever gets old and almost every line is quotable. Every. Single. Line.