The Room takes the cake, but that's a boring and predictable answer.
O hai Mark.
Anyway, how's your sex life?
Etc. Anyone can tell you why this is the best bad movie of all time, so here's another answer.
[video=youtube;MFLncfCvPeY]http://www.youtube.com/watch?v=MFLncfCvPeY[/video]
This was a big-budget summer blockbuster, so some people may question its placement here, but it really is an awful movie. It has an over-the-top premise, incorporating every disaster imaginable, it's emotionally manipulative in the extreme (there's a young cancer patient, Peter, who reads Peter Pan, for instance), and it's poorly-plotted. The dialog is atrocious. Characters make stupid decisions. It features a one-dimensional portrayal of a stupid George Bush and a (somehow redeemable) Dick Cheney. ICE CHASES PEOPLE.
That said, I have a soft spot for Roland Emmerich films. Independence Day, I still believe, is one of the best pure summer movies of all time. There is an optimism to that movie and its globalist message that is refreshing. The Day After Tomorrow is openly pessimistic, paying lipservice to a possible bright future in its last two minutes but otherwise hammering home the message that humanity has messed up. Turns out, Emmerich can convey that message with just as much shock and awe, though it's not half as gracefully executed.
It's fine. It's a great time. Its big budget shows in its special effects which are fun to watch, and everything else about the movie is (often unintentionally) hilarious. South Park parodied it in the episode "Two Days Before the Day After Tomorrow." That's a fantastic companion piece and one of my favorite South Park episodes of all time.