6. The Naked Gun
As fare as pure great jokes-per-minute, The Naked Gun is certainly in contention for greatest comedy ever made. I know that it's boring and obvious to bash the recent rash of "X Movie" comedies (the most recent of which, Disaster Movie, SURE LOOKS LIKE ONE HUH???), but if you really want to see how to do spoof right, look at The Naked Gun. When it does direct parody of other detective/spy movies, like it does of Telefon and Casablanca (not really a spy movie but whatever), it actually just lifts direct plot elements from those and puts them in the movie. See, Disaster Movie? It's funny because it emphasizes what's ridiculous about the original movies by restating those lines in a context where you're supposed to laugh. Juno breakdancing does not emphasize what is ridiculous about the movie Juno, which is plenty of stuff. Anyway, this movie has more specific gags that make me go "LORD I wish I had thought of that" than perhaps any other film.
5. Hot Fuzz
As this and #2 elucidate (no peeking!!!), I strongly believe that an underutilized genre combination is the action-comedy. Hot Fuzz is great because it is both a good comedy and a good action movie, and it doesn't make any sacrifices of one towards the other. Often times, even at a good action movie that isn't as much of a comedy (like, say Die Hard), you'll find yourself laughing in a sort of "this is ludicrous and I approve" way, so why not take that a step further and make a true comedy out of it? One thing I really like about Hot Fuzz is that for the significant amount of genre-parody they do, they never are insulting towards the action genre; they never condescend to the audience as to tell them they shouldn't be enjoying the somewhat mindless action parts of this movie for the sake of getting a cheap laugh.
Anyway, yeah, I love Simon Pegg and Edgar Wright and company, and I think this movie absolutely destroyed Shaun of the Dead (which I really liked) in all areas. This is maybe the only movie I have ever seen in theaters, and afterwards thought, "Well, maybe I shouldn't even try to go into the entertainment industry, because these guys are basically already doing what I would want to do, and really well."
4. Eternal Sunshine of the Spotless Mind
Boy, is this a well-written movie. It uses a backwards-told narrative, but does not at all feel derivative of Memento? It involves extended trips into the head of one character, but doesn't feel like rehashed ideas from Kaufman's earlier Being John Malkovich? It's about a technological procedure to erase the memories of someone with whom you've had a bad romantic relationship? Sign me the fuck up (NOT FOR THE PROCEDURE GUYS FOR THE LIST TO WATCH THIS MOVIE).
Really, Kaufman makes every scene in this movie count doubly. Watch the movie again and notice how basically everything comedic also has a dramatic purpose, and vice versa. It's a pretty tight movie, too (about 1:45) for all that it does. And wow, I'm not sure if I've ever really genuinely cared about a romantic relationship ending well in a movie as much as I did about Carrey's and Winslet's at the end of this. This movie is imaginitive in all the good ways without ending up having the pretension of other "extremely creative mind" movies. It's got something to say, but it tells you through fidelity to the characters and concept.
3. The Big Lebowski
When I was planning this list out a little bit ago, I was very seriously considering leaving the Coen Brothers off it entirely. Not because I don't wish I could write as well as they do--obviously, I do--more because I think of them as seriously on a different plane as me and most other people, such that it's almost insulting to them to imagine that I wish I had written one of their movies.
I know this sounds like near-religious idolatry, but yeah, I have near-religious idolatry for the Coen Brothers. Once I have seen the four of their twelve movies I still haven't seen (really, 8/12 seems like a pretty lame record for someone who considers themselves as big of a fan as I am), I'll do a list of their best movies, and I'm pretty sure Lebowski will be number one.
What I mean when I say that I don't think I could have written one of their movies is I tend to be a pretty formulaic writer, questioning myself pretty hard if beats or plotlines don't go in the "traditional" place. The Coen Brothers somehow both flaunt convention and make movies that are entertaining in the most classic way imaginable. Lebowski is basically a shaggy-dog story, where a man is being battered around by both his friends and enemies, taking very little initiative for himself, and just trying to get by.
So...why is Jesus in the movie? I don't fucking know. And what's the deal with the specific choices made in the acid flashback scenes, like Sadaam Hussein? I don't fucking know. And why does the film work as one of the greatest adventure/mysteries ever created? I don't fucking know.
It helps that the Coens have about the best ear for dialogue and the best sense of visual comedy of anyone ever making movies, but it's probably something more than that, something that I just haven't got. I watched this movie today, and god DAMN it is so good, and now I'm depressing myself becuase I'm not a fucking prodigy like the Coen Brothers are and will never create anything this amazing.
Also the best character is Walter and if you disagree you suck.
2. True Lies
By contrast, I feel somewhat more secure in imagining that maybe I could be able to write True Lies or something similar and good like it someday. It doesn't hurt that probably relatively few people think that True Lies is a brilliant piece of film the way that people think that Coen Brothers movies are, but also...in True Lies you can see the seams better.
True Lies is basically an action farce. That's how I describe it to people who haven't seen it in order to sell them on it. You have Arnold Schwarzenegger (God is he fun to watch, I don't care what anyone thinks about his acting ability) as a governmental secret agent whose wife (Jamie Lee Curtis) doesn't know about his real job, so when he suspects her of having an affair, she doesn't know that he's surveying her. Needless to say, the entire thing goes WAY out of hand, and both hilarity and tag-team husband-and-wife ass-kicking commences.
The REALLY great thing about True Lies's comedy, even better than Hot Fuzz, is that it never even attempts references to action movies. It's just a really great farce comedy that happens to center on people who live action-filled lives, so there is action as well, and farce, and fucking farcical action. If you can watch this movie without smiling your ass off and laughing the whole time, there is something wrong with you.
1. Dr. Strangelove
Well, yeah. It had to be. As some people may recall from this list, I'm a big sucker for well put-together satire, probably more so than I am for any other subgenre. Dr. Strangelove is terrifying because all of the awful and hilarious things that go on seem way too plausible. It's really a very broad movie, but it manages to be both over-the-top and relatably poignant.
Once I read someone try to make the claim that Dr. Strangelove isn't relevant anymore. Not relevant anymore? You've got to be fucking kidding. Replace communism with Islamic fundamentalism, and this movie could probably be retooled and remade today, and it'd be the most relevant political satire currently being produced.
I might go so far as to say that my TWO favorite all-time scenes from any movie are both in Dr. Strangelove, the Muffley phone call to Kissoff (PETER WHY DIDN'T YOU PUT MERKIN MUFFLEY ON YOUR LIST OF FICTIONAL PRESIDENTS AAAAAAAAAAAAAAAAAAAAAGHHHHHHHHH), and the Mandrake/Jack Ripper conversation about flouridation and purity of bodily fluids. Both of those are extremely good situational humor on their own, then made a thousand times as hilarious by both what hangs in the balance and the knowledge that there truly are people that stupid and loony in real life. God, this movie is good.