Although Spider-Man 3 was unsuccsessful by the critics and fans, fans demanded another sequel to feature Tobey Maguire. Sony took this to mind as they planned to take the number of sequels up to three plus a spin off to the third film's villian Venom. Sony argued that the time they had to make the film was far too short and cancelled the film in January 2010. In 2008, Spider-Man 4 entered development, with Sam Raimi attached to direct and Maguire, Dunst and other cast members set to reprise their roles. Both a fourth and a fifth movie were planned and at one time the idea of shooting the two sequels concurrently was under consideration. However, Raimi stated in March 2009 that only the fourth film was in development at that time and that if there were fifth and sixth films, those two films would actually be a continuation of each other. James Vanderbilt was hired in October 2008 to pen the screenplay after initial reports in early 2008 that Sony Pictures was in contact with David Koepp, who wrote the first Spider-Man film. The script was subsequently rewritten by Pulitzer-winning playwright David Lindsay-Abaire and rewritten again by Gary Ross in October 2009. Sony also engaged Vanderbilt to write scripts for Spider-Man 5 and Spider-Man 6.
In 2008, Raimi expressed interest in portraying the transformation of Dr. Curt Connors into his villainous alter-ego, the Lizard; the character's actor Dylan Baker and producer Grant Curtis were also enthusiastic about the idea. Raimi also discussed his desire to upgrade Bruce Campbell from a cameo appearance to a significant role. It was reported in December 2009 that John Malkovich was in negotiations to play Vulture and that Anne Hathaway would play Felicia Hardy, though she would not have transformed into the Black Cat as in the comics. Instead, Raimi's Felicia was expected to become a new superpowered figure called the "Vulturess".
As disagreements between Sony and Raimi threatened to push the film off the intended May 6, 2011 release date, Sony Pictures announced in January 2010 that plans for Spider-Man 4 had been cancelled due to Raimi's withdrawal from the project. Raimi reportedly ended his participation due to his doubt that he could meet the planned May 6, 2011 release date while at the same time upholding the film creatively. Raimi purportedly went through four iterations of the script with different screenwriters and still "hated it".
Since Sony thought this would happen, they planned and wrote a back-up script for a brand new Spider-Man reboot movie that Marc Webb took over and eventually turned into The Amazing Spider-Man (film), which was released to theaters on July 3rd, 2012.
Originally the villains in the movie were rumored to be:
- John Malkovich as Adrian Toomes/Vulture
- Anne Hathaway as Felicia Hardy or "Vulturess"