My friends often come to me for “Obscure Film” recommendations, since I’m the guy with a shelf full of DVDs that no-one else has apparently ever heard of. 
Most recently, I watched The Ninth Gate, which stars Johnny Depp as a second-hand book dealer who specialises in rare and antique texts. He’s hired by a mysterious Wealthy Collector to authenticate a book which, according to legend, was written by Satan. Since there’s more than one copy, and only one of them is the “original” text, he has to either authenticate his client’s text, or else acquire the “original” copy from one of the other wealthy and well-connected people who is known to have the text in their library. It’s a very well done movie- directed by Roman Polanski, I believe, and virtually no-one has ever heard of it.
I’m also a big fan of Hong Kong Action Films, of which my three favourites are Hard Boiled, A Better Tomorrow II,, and Kung Fu Hustle.
The first two star Chow Yun-Fat and involve him spending a lot of time wielding dual handguns and firing off a lot of ammunition- and as such are rightly regarded as classics of the genre, and the latter film starts Stephen Chow in a a movie that’s part traditional Kung Fu movie and part the opening act of Indiana Jones & The Temple Of Doom, with just a dash of Looney Tunes thrown in for good measure. All great films, and ones that only about four other people I know have ever even heard of, much less seen.
Some other good films that are worth seeing include the Western Purgatory: West of the Pecos, which is about a young man in the 1880s who wanders into a town that appears to be populated entirely by his heroes from dime pulp novels, Hercules Returns, which is a 1960s Italian Sword & Sandal film overdubbed by a group of Australian comedians (much like that game on Whose Line Is It Anyway?), with hiliarious results, Der Untergang (Downfall), about Hitler’s last days in the Fuhrerbunker (Bruno Ganz IS Hitler, and the film is just outstanding in every way), and Les Pacte Des Loupes (The Brotherhood of The Wolf), best described as a cross between a French Period Drama and an episode of The X-Files. The latter two films aren’t in English (German and French, respectively), but as long as you don’t mind subtitles you’ll find two excellent and very enjoyable World Cinema gems, IMHO.