Oh yeah. Brilliant. Small, intimate mess-with-your-head time travel short story if a movie.
After Dark, My Sweet - grimy movie with grimy people doing grimy things. Great acting except for Rachel Ward, who is sexy/sad at being a failed Rachel Ward.
Hotel Splendide – very strange British thing, because movies ought to be strange. Like, almost anything by Jarmusch (especially Dead Man and Ghost Dog: Way of the Samauri).
My choice is The Atomic Cafe. It’s a compilation of terrifying public service movies and newsreels from the early days of the atomic bomb and the Cold War. Watch and marvel that we were that stupid back then.
Maybe this won’t be considered obscure because of the famous “Bert the Turtle” cartoon that everybody knows about. But really, watch the rest of the movie.
I’ll second Stardust, Frailty, and Triangle.
I also enjoyed Idiocracy.
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Let’s Kill Uncle – a young (12 years old) heir realizes his uncle is trying to kill him for his fortune, and decides to kill uncle first.
Thanks for mentioning this, wish I could see it again. When I was young I read the book by Rohan O’Grady (who’s written some other good ones!) - one day I was dropped off with the other kids at a Saturday matinee and realized the movie du jour was based on the book! 
I second all of these. Great movies.
And I’ll third or fourth this one, with my standard caveat: TURN THE VOLUME OFF FOR THE FIRST FIVE MINUTES! The movie opens with a guy looking at the camera and giving away the entire plot of the movie, in what’s almost certainly a studio’s cowardly attempt not to alienate a mass market. The movie would be much, much better if it’s a mystery, not a mystery with the solution given at the beginning. WHen you see a single bare light bulb swinging on a wire, turn the volume back up.
As for my suggestion: The Fall (edit: linking to the AV Club review; it’s a good one). It’s a very strange fantasy with a frame story similar to The Princess Bride frame story, except the kid and adult are in a WW1-era hospital, and they’re both deeply disturbed, and the child actor doesn’t actually realize she’s acting, and the whole thing is beautiful.
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You are in luck! You can watch Let’s Kill Uncle for free online. It’s on Youtube.
And if anyone is interested, Passport to Pimlico is available through hulu.com
I second this, and have a slight correction. I found Lars and the Real Girl to be incredibly charming and sweet – and FUNNY! It says a lot about the best of small-town America.
And for the minor correction, it’s not an inflatable, its a “Real Doll”. I won’t link it, but it’s the first link when you google “real doll”.
J.
No one has mentioned My Dinner with Andre yet? Or how about Babette’s Feast?
J.
I want to nominate Zack and Miri Make a Porno. Surprisingly sweet and touching, even though it is, as the title suggests, about two long-term platonic friends making a pornographic movie. It even manages to be funny and sexy, as well.
Seconded. This movie doesn’t even need a plot (though it has one). It’s just one stunningly beautiful image after another.
Shaolin Soccer by the same director and with, IIRC, the same star, is more of the same if you liked Kung Fu Hustle.
If you’re into horror, then Stakeland is definitely worth your time. It’s an atmospheric, post-apocalypse vampire move. Much, much better than I expected it to be. It’s at 75% on Rotten Tomatoes, so I’m glad that I wasn’t the only one to think so.
Not so much underrated, but I’d suggest Tremors. An excellent homage to 50’s sci-fi horror films, and a funny film in its own right.
I have to share a little bit of Delicatessen… probably the most famous scene. 
http://www.youtube.com/watch?v=XJU4IwC3LjQ
I thought of another one, but it’s from the seventies. It’s a Jan Michael Vincent picture called Buster and Billie. It’s set in rural Georgia in the late '50’s, or early 60’s, and it’s a love story between a popular high school boy and an outcast girl. Extremely moving, but raw and shocking as well. I saw it as a double feature, having gone to see the other movie. I don’t remember the movie I went to see, but I remember Buster and Billie, these many years later.
My dad, who lived in rural Georgia at the time portrayed, saw it with me, told me the movie was extremely accurate in setting and atmosphere.
Oh, and Robert Englund played Jan Michael’s geeky best friend. This was way before Freddie Kruger of course. Fun.
Excellent suggestion. The basic premise is that two yokels Tucker and Dale are minding their own business in the woods when a bunch of horror movie teen stereotypes come to the erroneous conclusion that Tucker and Dale are serial killers and commence to accidentally kill themselves in increasingly hilarious ways.
I think the highlight for me was
when the kid dove head first into the wood chipper I still remember almost falling on the floor with laughter when I saw that. That movie is so full of greatness.
My contribution is Dan in Real Life. Steve Carrell does the ‘‘angsty widowed Dad’’ thing really well. It was such a sensitive and sweet movie. One of the few romance movies I’ve ever liked.
Also, for you reflective types, I really liked the South Korean film Spring, Summer, Fall, Winter… and Spring. It’s not like other movies; It doesn’t build to a climax and it isn’t designed to titillate. It’s just this movie about a Buddhist monk’s life and is beautiful in its simplicity. Hard to describe.
“You need to turn the safety off”
Well, I’ve added a lot of movies to my Netflix Instant Watch queue now.
Here’s my recommendation: Ravenous
It’s a horror/western/black comedy about cannibalism, with some Native American spiritualism thrown in.
If I’m reading the IMDB page right, this movie grossed around $3,000 in the US, and around $11,000 worldwide. Yet it had semi-famous actors — Thomas Jane, Aaron Eckhart, and Mickey Roarke — and IMO it was very entertaining.
It’s about a former drug dealer who has started a new life, but his past catches up with him on one disastrous day. It’s more comedic than gritty, but the comedy is understated.
^Yes, good movie! There is a very memorable scene with supermodel Paulina Porizkova.