Possibly the most infamous box office bomb of all time (the film’s failure bankrupted one of the oldest studios in Hollywood), Heaven’s Gate isn’t nearly as bad as its reputation would suggest.

HOWEVER, this is the longest movie on this list, clocking in at three and a half hours. It’s one of the slowest movies I’ve ever sat through, but I’ll be damned if the back half of the movie doesn’t have some of the best imagery in a western film I’ve ever seen, along with possibly one of the bleakest endings I can think of for any movie ever.