After Hours, 1985
A man named Paul, working in a soul-killing office job, agrees to meet up with an attractive woman, Mandy, he meets on a coffee break. What ensues is a nightmarish carousel of misunderstandings, misfortunes, and just plain bad luck as it turns out that everyone on this New York evening is somehow connected.
I keep thinking of analogies involving things like roller coasters because that's how this movie feels. While it is a comedy (at times leaning into the darker side of humor), it's main trick is an extended, unrelenting feeling of suspense as Paul first tries to get a dollar for subway fare and eventually ends up running for his life from various outraged parties.
The movie is filled with "Whoa, is that _____?!" roles: Linda Fiorentino as Mandy's eccentric roommate; Cheech and Chong as a pair of reformed thieves; Teri Garr as a waitress; Catherine O'Hara as (wait for it) a manic ice cream truck driver; John Heard as a bartender; Bronson Pinchot as Paul's co-worker. The list goes on and on.
The best thing about the film is just the way it is shot. I was going to talk about how much I loved a POV shot of keys being thrown down to a character, and then read in Ebert's review that this sequence was improvised on the night it was shot! The whole movie is full of interesting angles and zooms, but because the film is so slapstick and surreal, the boldness and obviousness of the camera doesn't feel jarring.
My only complaint was a relatively minor one. I felt like the writing of the different female characters overlapped a little too much (especially Mandy and Garr's character). No one is all that well developed anyway, but the way the women were written was a bit too similar in its portrayal of female neurosis. This is slightly saved by the excellent acting by the different actresses, but an extended scene with Garr really drove home this weakness.
Again, though, this was a minor complaint. Overall this movie was a blast and I really enjoyed it.