I might as well update again.
Brazil
This film seems to get more relevant every day. A world where everything is broken, terrorism, torture, endless paperwork, and only being able to escape such a depressing world by crawling into your own brain.
Amadeus
The worst and best biopic ever made. Worst because about 80% of this film isn't true. Best because the film knows it, and uses the life of Mozart as the grounds for a spectacular story about artisitc jealously. It's odd that a film so perfect should concern itself with the agony of being mediocre.
Eyes Wide Shut/A Clockwork Orange
I can't decide which Stanley Kubrick film I love the best. Eyes Wide Shut is a movie that you will, without question, hate when you first watch it. A Clockwork Orange is still relevant today in how it deals with violence and the way the world reacts to it....and you'll probably hate it when you first watch it.
Ed Wood
Remember in the 90's when Johnny Depp was awesome? Yeah, he doesn't - but every time both him and Tim Burton fail, this movie only gets better. The two of them could be convincted for war-crimes, and they would both be let off without charge because they made Ed Wood.
Alien
I remember first watching this five years ago and saying it was stupidly slow but it got really intense in the last 30 mins and the whole movie should have been just that. Welp, watching other horror movies and playing horror games - I've realised that 99% of horror movies and horror games are pure crap. I wasn't scared by Alien when I first saw it because hadn't really seen any horror movies and didn't know what horror was. Five years later, I realised I'd been looking at a masterpiece all this time.
Eternal Sunshine Of The Spotless Mind
A love story that actually feels genuine? Truly the universe has ended - and how appropriate that throughout this film you feel as though Joel is dying. Whenever I watch this I can't believe something so uncontrived yet surreal exists.
Adaptation
Thought Being John Malkovich was nuts? It is, and you should totally watch that movie too, but this takes things to a whole other level of meta. Films with this good a cast and this imaginative a script just don't happen anymore.
Fight Club
Alongside Monty Python and the Holy Grail, this is a prime example of a film that's been ruined by it's fanbase. Everyone watches this film and thinks: "Yeah! Screw capitalism! Screw materialism! I'm gonna buy myself a Fight Club t-shirt and continue with my dull life!" To anyone that's actually been through a psuedo-anarchist phase before realising how pathetic the whole thing is, this movie will hit just the rights spots.
Citizen Kane
Right, before you hit me with abuse - I've actually watched this movie. I've written articles and analysis's of it. I'm not blinded by the hype. I know this movie well, and everything I know about it is genius. The people who hate this movie are people who either haven't watched it, or have only watched it once before decrying it as overrated and going back to Batman.
This Is Spinal Tap
I can't really say what's good about it. Again, this is one of those movies that people are underwhelmed by the first time they see it - except for the oft quotes 'eleven' scene and that one moment that's the only real 'roll on the floor' gag. Quite simply, this movie is crammed with jokes; but they're not signposted. It's not like Hot Fuzz or The LEGO Movie where there are so many jokes you forget most of them - so when you watch the movie again it feels like seeing it anew. You rewatch This Is Spinal Tap and you discover jokes you didn't even realise were there before. The movie is so subtle I didn't even realise it was one of my favourite films until I tried to count how many times I've seen this and realised I probably watch it around four times a year.
Runners Up: Boogie Nights, Pulp Fiction, Downfall, The Seventh Seal, Pans Labyrinth, In The Loop, Spirited Away, Vertigo, The Wicker Man, Clockwise, The Good The Bad and The Ugly, A Scanner Darkly, Singing In The Rain, Groundhog Day, The Truman Show, Fear and Loathing In Las Vegas, Where The Wild Things Are, Hot Fuzz, Rashomon, The Assasination of Jesse James by the Coward Robert Ford - good god there are a lot of films I like.