The Daily Beast has a slideshow of Hollywood movies that bombed. I’ve only seen one of the movies on the list: Cleopatra. It’s a long movie, and as I recall the early-going with Rex Harrison as Julius Caesar was pretty good, but after he gets killed off, the movie goes downhill fast. What amazed me was the fact that Richard Burton and Elizabeth Taylor, famously having an affair at the time of the filming, had very little chemistry in the film. Harrison and Taylor were a better couple than Burton and Taylor, weird as it sounds.
Of course, the more expensive a movie is, the more danger it is in of “bombing”; since bombing basically means “failing to break even”. So, this means it’s theoretically possible that a good movie that people like could still bomb because of financial mismanagement during production. Since Cleopatra is the most expensive movie ever, it would have had to do incredibly well to not bomb.
So, what’s the best movie to bomb? Wikipedia has a list of the biggest bombs, that’s a good starting point. I know some people love The Adventures of Baron Munchausen, but I’ve never seen it. I haven’t seen most of these. Babe: Pig in the City wasn’t that bad… but it was pretty bad.