“Don’t tease me about my hobbies. I don’t tease you about being a pest.”
Monty Python and the Holy Grail
Well, my favorite films tend to change depending on my mood, and the list of those i love would go on for pages. But you want one, so…
I guess i’ll go with John Sayles’ Lone Star.
Every time i’m making a “Top ten” list in my head, it’s in there somewhere.
My favorite off-the-beaten-path movie is Bagdad Cafe. It looks weird, and it is, a little bit, but mostly it’s just a plain excellent movie and CCH Pounder is brilliant in it.
This sounds exactly like Wages of Fear. Is that an alternate title, a remake, or what?
Oh, and if I had to pick one that isn’t mentioned yet, I’d pick Heathers, but that’s only because it’s my favorite movie. 
The Mighty
Sorcerer is a remake of Wages of Fear. Directed by William Friedkin and stars Roy Scheider. I think it’s a worthy remake.
Heathers is a great film. I will always love Winona Ryder because of it.
[hijack] mrs danalan and I are among the few who saw this movie in the theatre, years and years ago. We both loved it – now that I know it’s on DVD, I’ll have to add it to our collection. [/hijack]
Aaahhh. OK. Might have to check it out.
Yeppers. She’s nummy. And it’s so brutally funny. “Because you’re an idiot!” Hee hee hee.
Ugh! Trust me, go out and rent it one day, you won’t be disappointed. It’s the brainchild of a man named, IIRC, Richard Williams. He wanted to be the first person to create an animated movie completely drawn by hand, by himself. He started it in the '60s, and by the '90s had thirty minutes finished. Finally Disney stepped in and animated the rest for him and added songs and dialogue. It’s so bizarrely beautiful, all the intricate Williams animation paired with the classic Disney style.
Another recommendation: The Journey of August King, 1995. August King (Jason Patric) is a man devastated by the death of his family. One day, he discovers a runaway slave (Thandie Newton) and decides to help her flee to the North. It’s about 4 hours long but it’s so good.
Recommendations (why would you just want one apiece?) with Netflix linked goodness, all the easier to add to the queue:
Dark City - saw this one in a film noir film class, blew me away. It’s in the list of movies that prove that good contemporary film noir is not an oxymoron. And the bonuses are great if just for two interesting commentary tracks. (I see on preview it’s already been mentioned, so I heartily second it)
Hedwig and the Angry Inch - not for the fainthearted, but really touching with great music and a very human story.
Real Genius - a SDMB comedy favorite. One of the movies that once you watch, you’ll start recognizing obscure quotes all over the place in threads (along with Princess Bride, as already mentioned by pinkfreud, from which my name is taken).
Secretary - kinky, dirty, disgusting, dark, and still both funny and touching.
Zoolander - it’s a stupid movie. I won’t deny it. It was so stupid that I refused to watch it for a long time. Then I was bored one day, and absolutely loved it. It’s idiot-savant genius.
Because the thread interested me, and I have a number of cinephile friends online right now, I decided to ask them for recommendations (ones that I have also seen and recommend are marked with an asterisk):
Bubba Ho-Tep
The Iron Giant
matchstick men
othello (90’s version with kenneth branaugh-sp?)
Dr. Stranglove
Hot Shots!*
Little Shop of Horrors (* for the musical version, I haven’t seen the cult classic B&W original)
One Flew Over the Cukoo’s Nest
The Gold Rush (gotta love some chaplin)
Donnie Darko
I Heart Huckabees
Harold and Maude*
The Crow*
Equilibrium
insomnia
life as a house*
freeway
I would have to agree on that. Great movie for a Sunday afternoon.
If you are looking for a classic comedy, there is nothing better than “Some Like It Hot”.
Have seen alot of the movies recommended here. Most are well worth the time on your queue.
Dang, you took mine. It’s not exactly obscure, I guess, but it’s at least semi-obscure. And a hell of a lot of fun. So second to Tampopo. (It’s a Japanese movie about food.)
Since flodnak picked mine, I get to name another: Wing Chun. A Hong Kong movie with Michelle Yeoh as an ass-kicking cross-dresser in feudal China.
I’m suprised no one has mentioned this one yet: Amelie
It’s a french movie full of quirks that leaves you feeling all warm and fuzy inside, as though you had eaten a cuddly wuddly kitten. It’s packed with wonderfully developed characters, funny dialogue, and great writing. Also, it’s very original and pretty strange. Everything about it is just downright pleasant. It’s a real treat.
Boondock Saints is a good pulp fiction. I second it. You can pick it up most places for $10.
Just added Bagdad Cafe to my queue. Watched the trailer and it looks like a lot of fun. Anything with Jack Palance in it can’t be all bad.
Just one, I’d have to go with Shakespeare in Love.
For something a little more off the beaten path (read: foreign), I’ll go with Talk to Her. (I’d go with Last Scene by Hideo Nakata, but it apparently doesn’t meet the “on DVD” requirement, which is a shame.)
Or, on another path together, Requiem for a Dream if you’re even thinking about doing drugs. 
I think I’m changing my answer.
Iron Giant, definitely.
No, rent the original 1997 one instead. Captures the mood much better. The remake isn’t so bad, as far as remakes go, but totally unnecessary, especially since it was made less than 5 years later!
Another of my favorite little-known movies: King Rat. This is one of the few movies ever made from a very good book that is also very good in it’s own right.