6. Spider-Man 4
What Was It: After the very disappointing Spider-Man 3, Raimi assured fans that Spider-Man 4 would be an improvement. Different stories suggest that Dylan Baker would have reprised his role as Dr. Curt Connors and that he would have finally transformed into the Lizard. But it seems that the main focus of the film would have been the Vulture, reportedly set to be played by John Malkovich. Anne Hathaway was also cast as Felicia Hardy. However, there are conflicting reports on what role her character would have served. In the comics, Felicia is the Black Cat, sort of Spider-Man's version of Catwoman (a character Hathaway would later play in The Dark Knight Rises). But in Spider-Man 4, she was apparently going to be the Vulture's daughter. And her alter-ego wouldn't be the Black Cat, but instead a new female version of the Vulture called the Vulturess. With the Lizard, the Vulture and the Vulturess all in the mix, plus Raimi saying that he wanted a bigger role for long-time friend and collaborator Bruce Campbell, it looks like Spider-Man 4 was well on the way to being just as crammed as Spider-Man 3.
What Happened: There were reports that Raimi and the producers were clashing over the choice of villains. With a fast-approaching deadline, the film would have been too rushed to do properly and Sony was already considering the possibility of a reboot. Once Raimi backed out of the project, the reboot was greenlit (much to my personal satisfaction).