To me a great film is basically anything that makes me think so much after the first viewing that a second viewing is unavoidable.
Fight Club (1999)
A crazy film. When it first released, the studio was so scared that an adaptation of Chuck Palahniuk's story about a "generation of men raised by women" would be so unappealing to the general public that they were forced to advertise the film as a literal "Fight Club". Now I was one of the lucky few who saw the film post-critical success; but when it hit the theaters it was a big flop. The problem was obvious: its commercials were attracting the wrong crowd. A masterpiece of modern-literary genius was being sold as an action flick. The result was underwhelming to say the least - but once the word got around about the film's actual plot of "moral impotency to global anarchy", the film was a critical success and a cult hit - and now, more than 10 years later, a rare post-release commercial success, thanks to DVD sales and collector editions. One of the first things that one learns in a screenplay writing class is that narration exhibits weakness in writing. Fight Club is a true exception to that rule, where the narrator is a separate character in itself. From fist-fights to vans filled with napalm explosives to clever & thought-provoking dialogues - the film inserts you in the mind of its unnamed narrator. At the end of the film we hope that there was a Tyler Durden in all of us, only to make us realize that there is, and how this fantasy world of Fight Club may become a reality if we let our Tyler Durdens run our lives. It's hard to do justice to the film's plot by trying to capture it in a couple of sentences - so all I will say to whoever hasn't seen Fight Club is go experience it yourself. And once you have, you will never forget the name "Tyler Durden".
Greatness Elements: Direction, the cast and characters, the plot.
The Dark Knight (2008)
This film made superhero films real. A sequel to Batman Begins (2005), the first true adaptation of the most complicated comic book hero, The Dark Knight was bigger and better in every aspect. Every other superhero, and by extension the superhero films, live in a world where almost anything is possible - mythical characters and creatures, superpowers, even time travel, among other things. But in the current Batman Franchise the only fictional element is the name of its city. Everything else is as real as any other drama film. It is not about a superhuman beating up bad guys with guns and getting the girl, but about a man who is struggling with his pain while protecting the lives of the few good people left in his city. The film makes you believe Batman can exist. With its plot, the cast, and especially the Joker, itt is perhaps the only super-hero film that didn't depend on its protagonist to excel.
Greatness Elements: Direction, screenplay, the Joker.
The Back to the Future Trilogy (1985-90)
A truly unique set of films that I wish I had experienced in person during its release. These three films, together and individually, have everything - action, drama, comedy, romance, and most importantly TIME TRAVEL. It is perhaps the only non-geeky mainstream sci-fi film. Directed by a man who has mastered storytelling and has a specialty in fantasy elements - Robert Zemeckis, who later directed Who Framed Roger Rabbit (1988), Forrest Gump (1994), etc. The story and mythology of these films will never get old, and it is perhaps the only one I would hate to see remade. The 70's and 80's of hollywood were ruled by two men - George Lucas and Steven Spielberg. Together, these two had 3 critically and commercially successful trilogies. George Lucas created the most successful film franchise of all time - Star Wars, one that has earned him over $10 billion over the past 30 years, making him have to never work again and still one of the richest men in hollywood. He and Steven Spielberg, who were and are great friends, collaborated on another franchise - Indiana Jones, with Lucas as writer and Spielberg as director. The third franchise, produced by Spielberg, was Back To The Future. Today, a film franchise is no longer governed by the same rules. Nowadays no matter how absurd the story may be, any film that earns twice its budget is "green lit" automatically by the studio for a sequel and a possible franchise. It has come to a point where the studios are forced to make more money. An example would be the recent comedy The Hangover (2009), which is getting a sequel for no other reason than to recreate the luck it had the first time. Besides the exception of the current Batman franchise (which may still be spoiled due to the studio forcing the director and writer to make the third film since the second one made over $1 billion), the Back To The Future trilogy is perhaps the last franchise where the sequels were made only because the creative team behind the films believed they were important to the overall story, and the "The End" at the end of the third film was taken seriously. However, I wouldn't be surprised if in the years ahead we saw a "re-imagination" of the franchise, something I would always be skeptical about as a huge fan of the originals.
Greatness Elements: Story, characters, and the crazy situations they find themselves in.
Greatest Hollywood Films of All Times: Part III - Pixar
Greatest Hollywood Films of All Time: Part IV