2. Al Pacino - Jack & Jill/Gigli
The possibility that someone growing up today might have seen Al Pacino in Jack & Jill or Gigli and not know about the rest of his extensive body of work actually terrifies me. We certainly expect better from our legends. They should really know better. Especially in this case. These weren't movies that just happened to be bad despite everything. These were films that no reasonable person could have thought was a good idea. With a few exceptions Adam Sandler's movies fall into one of two categories: painfully awful or guilty (but equally awful) pleasures. Jack & Jill fit perfectly in the former. There's actually a YouTube video out there that claims to show all of the film's funny scenes. It's 56 seconds long, and that still seems generous. And as for Gigli, an actor of Pacino's caliber probably should have been able to predict that attempting to capitalize on the "Bennifer" celebrity couple craze might not make for the most compelling film. Fortunately for Pacino, no one saw either. Whew!