14. Jack and Jill

[youtube=http://www.youtube.com/watch?v=qHKTXrUnN58&w=584&h=390]

Jack and Jill is a movie I end up talking about often — because it has a way of burning itself onto your brain. It’s not just awful. It’s fascinatingly terrible, the kind of movie whose badness should be studied and picked apart as a lesson for future generations. Jack and Jill is a movie that’s just made wrong, showing no knowledge of plot structure, character development or how any characters behaved. This film is what would happen if we asked aliens to watch Pauly Shore movies and then write a script about dysfunctional siblings.

What’s strange is that the movie seems to be trolling itself, as if it knows a script in which Al Pacino rapping about Dunkin Donuts is bad. (It’s even worse than you could ever imagine.) In the film’s final lines, Pacino begs Sandler, “All copies must be destroyed. It’s no good.” He’s not technically talking about the movie, except that you know he is.