The Matrix
Any movie that combines pseudo-Zen philosophy, Plato's allegory of the cave, Through the Looking Glass, kung fu wuxia movies, and Ghost in the Shell-style cyberpunk robot-fighting is okay by me. Although it's not nearly as deep as the Wachowski brothers would like to think, it's at least more comprehensible than your average philosophical anime, and it doesn't involve everyone in the world being turned into Tang.

As something of an armchair philosopher and a prophet of doom and gloom, The Matrix's themes of questioning reality and the nature of our existence (Hint: "reality" truly is just impulses from the outside world filtered through the shell of meat out brain lives in, so we don't really experience the world directly.) touched me in ways I hadn't been touched since that smelly old man molested me in kindergarten. Wait, that never happened.
At any rate, the movie's two sequels weren't as successful, although on repeated viewing, Matrix Reloaded's themes of determinism versus free will definitely grew on me. Don't ask me what Revolutions' theme was. Maybe instead of "What is reality?" or "Do I really control my destiny?" it's "What can we do to get more money?".
Serenity

Above the unlikelihood that this would (or should, given that God hates us) have ever happened, Serenity has strong moral and philosophical underpinnings, but doesn't confront the audience as openly about them as, say, Star Trek's often-cumbersome moralizing. This movie may have space cowboys, mercenaries, ruthless secret agents, hookers, and a psychic killer girl, but it's really about the nature of freedom, outside control, and where good intentions take you. We are and should be free to choose our own paths, as the Libertarian-like Browncoat preaches. Even with the best intentions, attempting to control people too tightly results in disaster. You can't force people to be "better".
Ironically enough, the Chef is in actuality a fascist who believes we need stricter government controls to prevent irrational idiots from fucking things up even more than they are. But hey, the whole Libertarian philosophy of making one's own choices is nicely romantic. It tickles me in an imaginary way.
I'd also like to shoot forcibly sodomize lock in a room with Pauly Shore and Richard Simmons draw and quarter the jerk at Universal that decided not to openly market this movie and to instead rely on word of mouth. That was a screwup on par with some knotheaded Fox executive's decision to schedule Firefly in the Friday Night Death Slot when nobody remembered to watch it because people have better things to do on a Friday night than watch TV, dammit. On behalf of all Browncoats everywhere, I'd just like to say "Fuck you, asswad executive. Thanks for nothing."
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The Maitre d'
Star Trek IV: The Voyage Home
I think the only reason I liked so much it was because it was so funny. Shatner is a brilliant comedic actor (or maybe just bad enough that he naturally excels in comedic situations) and the rest of the cast aren't too shabby either. That, and it was set on modern day Earth. My opinion of a movie/video game/location is based very heavily on how much I like the setting. (More on that when I respond to ESB.)
Obviously the plot sucked. I'm pretty sure it was just an excuse to get the crew of the Enterprise to go back in time to the present-day. It's one of those completely-illogical-tree-hugging plots like Captain Planet. If they wanted to be truly environmentalist, they could have the heroes fight against something actually threatening the world/environment/whatever, which would require a lot of time and effort to develop as a plot. Instead, they create an alien deus ex machina that needs to communicate with whales to reinforce the message, "If you let the whales go extinct, you'll all be really, really sorry. Don't say we didn't tell you so." It's the environmental equivalent of Left Behind.
I also liked Generations. I think that's the only ST film I actually saw in the theaters. Despite my lifelong geekishness, I didn't really watch that much Star Trek (a bit of TNG, and then DS9 and Voyager pretty regularly for a while), but I know enough of the concepts and lingo to account for the rest. (For that matter, I came into Star Wars fandom rather late in my teenage years.)
The Maitre d'
Empire Strikes Back
I think the main reason is that the settings of ESB just don't appeal to me like the settings of ANH and RotJ. The majority of time in ESB is spent on a desolate ice planet, on a desolate jungle planet, in the desolate void of space, on the bridges of starships, and on a floating city. OK, that last one isn't so bad, but the first few just aren't my style.
I'm not sure what it is, but a lot of my emotional reaction to a movie, book, or game is based on how much I connect with the setting. Case in point, I hated making Jedi Knight levels that used a lot of metallic textures, but I loved making outside or cave levels. And I have a much easier time drawing organic stuff than I do filling in the details of robots or starships.
And yeah, the fact that the main characters spent most of ESB traveling hither, thither, and yon didn't help. Too much travel back-and-forth, not enough purposeful action.
Let the psychoanalysis of my preferences in games and movies begin.
The Chef
So....
reaperman
Interesting list.
The Chef
Is that all?
reaperman
Pretty much.
The Chef
So...
reaperman
Oh, no you don't.
The Chef
On the contrary.
The Maitre d'
OK.
And I say that as someone who has started a lot of very useless comment threads on this site.
The Chef
So post something useful.
reaperman
Yeah.
The Chef
I've noticed...
reaperman