Super Troopers, Billy Madison, and Office Space are three pretty funny movies that bombed. Fight Club is another one that didn't do well in the theater but is considered a classic. Grindhouse (Planet Terror/Death Proof) also did poorly in the box office but is a hell of a lot of fun to watch (especially the extended versions with the extra fake trailers). BTW, Machete is being made. But the ultimate example is Blade Runner. Extremely good movie that gets better with repeated viewings. Released alongside E.T. and was totally overshadowed in the box office, IIRC.
Great call on Super Troopers and Office Space. I hated those two movies the first time I saw them but have come to be two of my faves.
The Big Lebowski. The Coen Brothers film before the Big Lebowski was Fargo, and every critic wanted to see what they would come up with next. The Big Lebowski was laughed at by critics, did terrible in the box office, but you might say it's their most popular movie. Huge cult following and one of the funniest films ever made.
I don't think some people know what a bomb is. Waterworld fits the definition to a T. A movie "bomb" is a would-be blockbuster that does not sell many tickets. Remember, in Hollywood, money talks and bullshit walks. A crappy movie that makes tons of money is a success.
Yeah, Office Space and Super Troopers probably lived up to expectations and I love both of them. Waterworld cost something like 300 million if I remember correctly, and I think at least one person was killed making the rotating sets in the ocean. They could make the same movie with better effects today for 30 million easy. It just wasn't a horrible movie, but it clearly wasn't worth the money they put into it. It wasn't a great movie either, just not horrific.