Saw this on Battle of Alberta and I thought I'd do it.
1. Worst well-regarded film: This one's easy: Lawrence of Arabia. Four hours of walking through the desert. All style, no substance, and it's AFI's #5 movie of all time.
2. Most overhyped film (note that this is slightly different from above; the first measures the absolute badness level, while the second measures the delta between reputation and actual quality): I imagine that once I see The Dark Knight, that will be the answer to this question. The fact that it's on the top of IMDb's Top 250 is a really good indication of hype. For now, the answer to this one is The Matrix.
3. Worst film to win a best picture Oscar: Most of you are probably expecting me to say Million Dollar Baby. The only reason I'm not is because it was pulled from a weak crop of films that year. In the end, I'm going to have to go with The English Patient. It beat two vastly superior films: Fargo and Shine. Just die already! Nobody cares about your time in the stupid desert!
4. Most disappointing film (ie should have been good but wasn't--Godfather III, Phantom Menace, the latest Indiana Jones atrocity) It's hard to remember a film that was supposed to be good. Generally, they fall off the face of the planet and aren't heard from much. I seem to remember that The Legend of Bagger Vance was supposed to be good, and was god-awful. I'll never go to another movie that was recommended by Oprah.
5. Worst movie, full stop. (Must have been a major motion picture release--no direct-to-video, or film festival torture tactics, please) Very tough call here. There are a lot of terrible movies out there, but a lot of them can be appreciated at some level due to their camp value. No, a truly terrible movie is one that tries to be good and then badly misses the mark. I don't think one can argue that Daddy Day Camp and Norbit ever try to be good. Therefore, my worst movie ever? Continuing with the Matt Damon theme from the previous category: Pearl Harbor.