OK here's some kind of rudimentary top-10 list.
1) O Brother, Where Art Thou?
I grew up in the south, and all of my family is from the south, so the aesthetic of this movie, although antiquated feels like home. It's a gorgeous looking film. The sepia-toned adjustments they did to the film make it seem depressed, which works, because at its heart it is a clever quirky film about the Great Depression. The acting, the pact, the music, all of it comes together in a very special movie for me. The music. It was good enough to win Album of the Year as a soundtrack. It's Southern Gothic Noir but funny, and who else could do that but the Cohens.
2) The Right Stuff
This is a historical movie that could have been really dull to look at, and chock-full of boring American patriotic tropes. But it's not. For one, the book it's based on is crafted in such a way as to mimic the emotions and perspectives of the test pilots. They don't get the hoopla. They don't understand why sitting in a rocket you cannot actually fly is such a huge deal to everyone. So scenes like the announcement of the Mercury 7, when the journalists are flipping out and the astronauts are sitting there feeling uncomfortable, you're getting their side of the fence. In the same way, the movie is beautiful. It almost feels at times like they chopped the movie up and gave it to different arthouse directors and cinematographers to shoot. The silent horserace through the desert. Breaking the sound barrier. The training sequences. It feels like an indie movie at times, and it does it a big favor. It's the story of heroes who don't really know they're heroes, and it's told in a stunning way.
3) Memento
What can I say about this movie. I saw it after all the hooplah about it, once it was out on VHS. I rented it. It was everything it actually is. I ended the movie going "Jesus fucking Christ" and feeling like I needed to immediately watch it again. That ending. What a dark, dour, sad, pessimistic ending. That ending leaves a taste in your mouth. A bad one. In a good way.
4) Casablanca
Picture me, 19 year-old-Jeff, in an introductory-level freshmen film class in college. It's called "Cinema Studies," and we watch movies and talk about them. Professor says he's putting on Casablanca, and I kinda groan. I don't want to watch some dumb old movie that old people talk about. I want to watch something cool and awesome, like Memento. And they I watched it. And every single part of that movie's fame made sense to me. Yes, it's got some cheesy old-school Hollywood shine to it, like the really blurry lens when they cut to Bergman. But the shadows. God, the shadows. The acting. Bogart's stone face as he crafts his plan. The scenes. Him getting piss drunk after she shows back up, showing the vulnerability of his hard-ass character. The end. That fucking ending. Fuck it, it's one of the few classic films that deserves every praise it gets. Which brings us to...
5) 12 Angry Men
Lots of people have listed this one so far, so I cannot think of anything to say that they didn't, except to say that this movie knows pacing better than any other movie. Think about the movie like a piece of classical music. It lulls, then grows in tension and pace until BAM, you get the knife scene. And what follows it? Arguing, that slowly lets off, until people are back calm again.
6) The Great Escape
It's a movie that, despite being an ensemble cast wherein people really want to get their own airtime, wasn't afraid to minimize Steve McQueen, arguably their biggest star, until the very end. And that makes for a great series of smaller stories within the bigger story.
7) Apollo 13
How do you make people feel suspense in a historical movie? A lot of people don't even try. The audience knows the ending already. In this case, (almost all of) the audience knows the ending already. Usually, directors take the approach of simply making your historical drama be really over-the-top with visual effects, or additional pieces of the story are added to keep people's attention (Ala, Titanic). Ron Howard went the opposite route with this one. What if, for a historical drama, you use good ol'fashioned Hollywood tricks, like big camera sweeps, tight emotional shots, manipulating time, to create a real feeling of suspense in a movie everyone already knows the ending to? That's what Ron Howard did. And he made a masterful piece of cinema.
8) Bullitt
Bullitt is so fucking cool. I want to dress like him. I want to lean against things like he does. I want to carry a shoulder holster under a tweed blazer like him. I want to get a 1968 Ford Mustang Fastback. I want to be melancholy about my own role in a violent world. I'm not a film historian, but I do think this movie invented the idea of your star detective in a cop movie not being Mr. Johnny American Gonna Catch The Crooks And Beat Them Up. The character, Bullitt, in the movie, is kind of a mess. He's not got it all together. He cannot keep a romantic partner. He lives in a sloppy one-bedroom apartment. His weekly diet consists of frozen meals he picks up at the local Chinese corner store. He chugs tomato juice to try and recover for the next day of work after sleep an hour and a half. He's a mess. But the vulnerable cop trope is one I think you can trace back to this incredibly stylish detective story.
9) Zodiac
This is a criminally (lol) underrated and under-appreciated movie. This movie should be fucking awful. How do you make a movie about an unsolved crime? Do you just pretend to solve it at the end? Fuck if Fincher didn't up and do it. He crafts the movie to be about the people who are either directly (cops and detectives) or tangentially (reporters and a cartoonist obsessed with puzzles) connected to the case, how it impacted them, and their own obsessions about catching an obsessive killer. The way it handles the mystery of unknown is spectacular. Even in the end, where you're kinda pointed into the direction of who you think should be the suspect, you still feel doubt. Just like actual detectives felt about this case. Also, in proper Fincher style, the whole thing looks dark and murky and grey.
10) The Social Network
Some of this is biased by the fact that I research social media for a living, but I really do love the story this tells, and how it tells it. Making a movie based on a current-day pop-culture monolith is hard to do, but this movie treats it well, giving split time between how the thing itself came to be, and the kinds of people who would make such a thing (Or claim they did). Sorkin was well-suited to writing it too, as the kinds of Harvard assholes who would sue each other for billions of dollars would talk like an Aaron Sorkin script.
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