Top 50

So anyway, I'm going to take a break from ceaseless self-analysis because it's a hugely self-indulgent and masochistic exercise.  Writing, on the other hand, is not.  I figured that in order to be able to call myself a proper film guy it's important that I list my favorite (and I'll admit this is nowhere close to a perfect list) movies and a brief description of why I like them. Keep in mind that I tried to be inclusive of all genres and that beyond the first eight or so the order stops being relevant. 

1. Eternal Sunshine of the Spotless Mind - This is the movie against which I can safely judge the quality of most other movies.  The plot?  Bulletproof idea.  The acting?  Oscar-worthy.  The screenplay?  Oscar-winning, in fact.  But the real success of the movie comes from the fact that it dissects the oft-pondered and nigh-imponderable topic of love and companionship in a highly surreal and cerebral fashion. 
2. Willy Wonka and the Chocolate Factory - My love for this movie relies hugely on nostalgia and the fact that watching it is magically faith-restoring.  Pure Imagination is without a doubt my favorite song of all time, too.
3. Pan's Labyrinth - I've only seen this one time but it left a huge impression on me.  A lot of my favorite readings revolve around magical realism, which this movie embodies better than any other that I can think of.
4. Almost Famous - Coming-of-age stories don't get much cooler than this.  Almost perfectly captures what it's like to be a young teenage boy while at the same time telling a larger-than-life and largely true story.
5. City of God - This is the movie Slumdog Millionaire wanted to be and whose heights it couldn't reach.  Also, this has some of the most beautiful cinematography ever. 
6. Inception - This movie made me realize that all other movies are just condescending.  Few movies are this elaborately and well plotted and the fact that it manages to be simultaneously gripping is a huge accomplishment. 
7. Children of Men - One of the best depictions of dystopian sci-fi in movies with gratuitous long shots that I have always found far more engaging than the typical fast cuts you'd find in these sorts of movies to mask CGI effects, etc.
8. The Diving Bell and the Butterfly - It's impressive enough for the first 30 minutes of a movie to be interesting and engaging while taking place from the same perspective in the same room.  It's even more impressive for a movie to create such a detailed, emotional, and beautiful portrait of a man locked in his own body. 
9. Ferris Bueller's Day Off - I shouldn't have to describe why I love this movie, you probably understand it.  But I'll let you know that watching this movie under the popular fan theory that Ferris is just a figment of Cameron's imagination makes the movie a masterpiece. 
10. District 9 - In case you're wondering why this movie is ranked so high, it's because I appreciate that it exceeds all expectations for its plot and characters.  Few movies succeed as well on so many levels - effects, acting, plot, cinematography, dramatic effect, etc.  Despite the fact that it is decidedly less award-baity than most other movies on this list it gets a higher rank. 
11. The Big Lebowski - I know a lot about the narrative structure from reading TV Tropes like a madman, but how this movie was constructed will always escape me.  Hilarious.
12. Groundhog Day - Despite its nearly ubiquitously poor execution in movies and TV, time travel is one of my favorite plot devices and this movie is one of the few to be able to do it right. 
13. Kill Bill -The modern standard for revenge flicks, and Tarantino's best for those among us (me!) who found Pulp Fiction to be a bit too indecipherable to be better than this.  Although if I were being realistic with my selections and wasn't trying to include as many directors and genres as possible, both Pulp Fiction and Inglorious Basterds would also be on this list, and very high.  
14. The Neverending Story - Childhood classic that has somehow actually improved with age, unlike most products of the 80s. 
15. Brick - Film noir + high school + Joseph Gorden-Levitt = Awesome.
16. Oldboy - More revenge?  This movie covers the same ground as Kill Bill but somehow in an even more melodramatic, violent fashion.  
17. Big Fish - Tim Burton's best movie ever, probably because it was one of his least macabre.  He needs to do more like this instead of shit like Alice in Wonderland.  
18. Avatar - Shut the fuck up, this movie made you jizz in your pants when you saw it and anybody who disagrees is a damn liar.  The fact that this manages to work even with a cliche storm of a plot is evidence that tropes are not bad. 
19. Once - A musical with a score that isn't mixed poorly might be all that's necessary to beat the rest, but the fact that it still manages to be good in all other respects is admirable. 
20. Grizzly Man - This movie is the best documentary I've ever seen, ever.  Basically a complex character study, except with fucking bears.  I almost wish it weren't a documentary so people don't avoid it for that label, because this movie is utterly fascinating.
21. Where the Wild Things Are - This is the only kid's movie ever to capture what it actually feels like to be a kid as opposed to the way filmmakers typically perceive kids as feeling.  A hugely nostalgic experience.
22. Good Will Hunting - A movie about wasting potential.  I don't know if I have potential, which is exactly why it's being wasted.  If there is potential for anything you can never know if you're wasting it or not, and I find that terrifying.  This movie slides onto the optimistic side of the scale, with the protagonist realizing he's capable of being better than he is, for lack of better words.  Pretty much the opposite of...
23. Greenberg - Believe it or not, I really don't like Noah Baumbach all that much, but this is the one movie of his featuring one of his trademark terribly unlikeable protagonists that actually made a scary amount of sense to me.  I like it a lot more for its personal meaning than for its artistic merit.  Speaking of which...
24. Vanilla Sky - I can't tell you how much I should hate this movie... but its got far too much in the way of narrative structures I actually like to really hate.  Character-driven science fiction in the same vein as Firefly, Eternal Sunshine and Vanilla Sky is the best genre for examining the "what-if" questions in a way that is actually fulfilling because the protagonist's journey is identical to the viewer's, even especially if the protagonist is a jackass. 
25. Mulholland Dr. - I almost gave up on this movie based on the fact that it didn't seem like anything but the TV pilot that I later found out it was supposed to be for the first hour or so.  But once Naomi Watts reveals her character's hidden depths (i.e. the audition scene) the movie becomes one of the most massively cerebral and engaging experiences to be seen on film.  
26. The Fountain - Yeah, fuck me for putting what many consider to be Aronofsky's worst movie as the best, but this movie has a better plot, writing, and acting than people give it credit for in addition to some of the best cinematography and the single best score of all time.  
27. The Blair Witch Project - I realize that these past several choices have all been controversial, but this movie was deeply unsettling because the idea of getting lost is something that I've never seen explored as in-depth as it was here in the horror genre despite the fact that it is a terrifying experience.  Mission accomplished, stupid dead teens in the woods. 
28. Danny Boyle - I can't choose between his movies.  It's like asking to pick a favorite child, and if I could I would pick all of them.  Trainspotting, Millions, 28 Days Later,  Slumdog Millionaire, 127 Hours and even the weird "slasher in space" Sunshine are all favorites because even though they often cover very dark, grim subjects, few filmmakers can capture the sensation of happiness on film quite like Boyle.
29. The Matrix - For the same reasons everybody else likes them.  The sequels are good too, despite popular opinion on the matter, if only for the action scenes.  I remember the freeway chase and the battle in Zion more fondly than any action scene from the first one, even if the latter two are overwritten and sort of nonsense. 
30. Serenity - I enjoy watching this movie whenever possible due to the fact that it is the conclusion to my favorite show of all time, Firefly, but it also works very well as a standalone.  One criticism from the standpoint of a fan of the show is that it isn't as heavily invested in all of the characters as the show was, but that makes it quite a bit easier to follow for an outsider than one might think.  In fact, I saw the movie before I'd even heard of the show and enjoyed the idea of the Space Western quite a bit.
31. Spaceballs - Spoof movies are a genre that needs to be vindicated, and I'm afraid that the genre has been thoroughly killed and buried by the shit shoveled out by Jason Friedberg and Aaron Seltzer.  If there is ever to be any evidence that spoofs were ever good, look to Mel Brooks.  This one is a personal favorite of mine. 
32. Being John Malkovich - Malkovich Malkovich Malkovich Malkovich Malkovich Malkovich.
33. (500) Days of Summer - At the time that I saw it, possibly the most uplifting movie ever made.  Now, a guide for the neurotic young adult on how the world of love and relationships works.  Owes a lot to Eternal Sunshine despite being a far less complex viewing experience. 
34. Howl's Moving Castle - I recognize the superiority of Spirited Away, but this is a list of my favorites, not the list of the best movies I can think of.  This is the movie that got me into Studio Ghibli and it is undoubtedly one of their better products.  Princess Mononoke and Spirited Away get honorable mentions. 
35. Harry Potter and the Prisoner of Azkaban - Appreciated above all others for its artistic merit and (sorry) epic time-travelling finale.  Despite the fact that the previous two movies were higher-grossing and the plot of the books doesn't come to the turning point until the end of the Goblet of Fire, this was the game-changer for the movies as it demonstrated that they were more than stiflingly faithful adaptations of the novels, that these children can act, and that time travel doesn't suck.
36. Shawshank Redemption - I am not a film critic.  This movie doesn't embody the sort of mastery that has earned The Godfather or Citizen Kane or anything their labels as the greatest films ever made.  But I'll be damned if this isn't one of the most uplifting, soulful, resonant movies ever made, and it's unfair to judge cinematic greatness on terms outside of the impact on its audience.  Speaking of which...
37. Toy Story 3 - The first movie created a new art form and did so with style.  The second movie demonstrated that this art form wasn't a gimmick and could convey emotions as well as a live-action film.  The third reduced this man to weeping like a little girl.
38. Primer - If you haven't picked up on it yet, time travel gets a bad reputation due to the number of instances in which it is demonstrated poorly.  This is the example of time travel plots done right.  The events of the plot are confusing as fuck but the time travel mechanism is explained, and the paths of the protagonists through time are clear.  Also notable for being a champion of low-budget cinema.
39. Let The Right One In - The timing of this movie amidst the Twilight-fueled vampire craze is hilarious, because I get the feeling that the vampire romance in this movie is exactly what Twilight was aiming for but instead got the exact opposite - both the genuinely frightening implications of being in love with a monster and the inherent sweetness of the relationship between the leads drive the movie.
40. The Fox and the Hound - My favorite Disney Animated Classic, for obvious reasons.  Anyone who doesn't like this movie has no soul.
41. Leaving Las Vegas - Damn depressing.  I watched this movie with the belief in my head that, against all odds, the main character would stick to the predicted narrative structure of overcoming his addiction and getting the girl.  Nope.  Two hours of a man drinking himself to death.  
42. I Love You, Man - A movie starring Jason Segel and Paul Rudd about the beautiful relationship known as bromance.  What's not to love?  Also notable for being the source of many phrases that have actually entered my everyday speech (and the phrase "totes" which has entered everybody's everyday speech).
43. The Truman Show - Duh.  Let's see what else is on.  
44. Donnie Darko - A must-have for a list containing lots of critically-acclaimed films involving time-travel.  Too bad Richard Kelly is like the M. Night Shyamalan of indie movies.  Apparently this movie being good was an accident.
45. Dark City - A movie that caught me off-guard.  I was expecting a movie similar to The Matrix, which this is compared to all the time.  They are similar in terms of their simulated reality concept, but beyond that they share almost nothing except being good.  One thing I liked more than The Matrix was how the ability to alter reality at will - essentially being the God that Neo was made out to be over the course of three films - was deconstructed more completely in five minutes.  
46. House of Flying Daggers - I needed to include at least one martial arts epic.  I used to watch a ton of them, for a reason that mostly escapes me to this day.  This movie is over-the-top gorgeous, dramatic, and thrilling.  
47. The Lost Skeleton of Cadavra - I couldn't not include this.  An extremely affectionate parody of cheaply-made 1950's era sci-fi B movies that is so realistic you'd almost mistake it for one at first glance if you didn't understand those sort of Earth jokes.  
48. The Dark Knight - Easily the best superhero movie since the revival of the genre in the late nineties.  I shouldn't have to explain why because you've seen this movie.  
49. The Crow - I'd intended to see this for a while simply due to its awesome soundtrack, but I didn't anticipate the movie to be so... cool.  I mean, a lot of that is probably owed to the comic, but the main character is immune to bullets, kills people off in awesomely brutal fashion, plays guitar on rooftops, is crazy good at parkour and kung-fu, and wears clown makeup while doing all of those things to really angry 90s alternative rock.
50. The Royal Tenenbaums - Wes Anderson saved the world with this movie. With a movie invoking the dysfunctional family reunion trope you would expect a feature-length sitcom, but instead get a dramedy where each and every character is interesting, endearing, and believable despite their unbelievable lives.  That just goes to show you how far acting chops can get you.