Here's a film that the distributor had such a difficult time with, they took the rare step of releasing it twice in the same year, and still couldn't figure out how to draw an audience:
It's from 2000, and was directed by Curtis Hanson, with a screenplay by Steve Kloves (who went on to write the scripts for all but one of the "Harry Potter" movies), based on a novel by Michael Chabon. The cast included Michael Douglas, Frances McDormand, Robert Downey, Jr. (before he was "Iron Man"), Tobey Maguire (before he was "Spider-Man"), and Katie Holmes. Bob Dylan won an Academy Award for his original song "Things Have Changed", which is probably now more famous than the film itself.
I think it's a perfect movie. The writing is great, and the acting is wonderful -- each actor inhabits his role perfectly, and they really bring the characters to life in such a way that when it ends, I always want to spend more time hanging out with these people. Great direction and cinematography, all brought together with some really good editing that makes perfect use of both the film's original score and a wonderful selection of songs that the director chose to use.
This is easily on my top five favorite movies of all time (truth be told, it's probably #2), and yet no one has seen it. It's on DVD, but not available on Blu-ray, nor on any streaming or digital sell-thru site. The trailers and posters for the movie do a pretty lousy job of making it seem like it's worth seeing, to the point that when Paramount first put it out in Winter 2000 and it flopped, they decided to re-release it theatrically in October 2000 to try again -- and still couldn't get it right.
With Robert Downey Jr now one of the biggest movie stars in the world, Tobey Maguire's stature also being a lot higher than it was, and Michael Douglas having had a comeback of sorts with "Behind the Candelabra" and the upcoming "Ant Man", I'd love for more people to discover this movie.
PROS - Fantastic writing, great acting, nice direction, brilliant soundtrack
CONS - It's a character piece with moments of levity and moments of drama, but it never settles firmly into one genre -- some people might not appreciate a movie that is comfortable not falling squarely into an easily identifiable genre. And the marketing campaign sucked -- if you're the kind of person who normally decides whether or not to see a movie based on a trailer or posters, in this case please, please ignore them and just see the film!