In 2002, Tobey Maguire debuted as Spider-Man in the character’s first live-action film. In 2003, he sustained an injury on the set of Seabiscuit that created doubts as to whether he’d be able to do Spider-Man 2. Director Sam Raimi decided that, in the event of Maguire being unable to return, the new Spider-Man should be Jake Gyllenhaal. Before Gyllenhaal decided whether he wanted to do it, Maguire recovered and went on to complete the trilogy. During this time, Gyllenhaal won an Academy Award for his supporting portrayal of Jack Twist in Brokeback Mountain.
In 2017, Spider-Man was rebooted in Spider-Man: Homecoming, starring Tom Holland as Spider-Man and former Batman star Michael Keaton as Vulture.
At the same time, Batman was now being portrayed by Ben Affleck in Justice League, and rumours were beginning to abound that he was to be replaced by Gyllenhaal.
Gyllenhaal confirmed that he had been in talks to star in a standalone Batman film but had passed.
Deadline‘s Mike Fleming is now reporting that Gyllenhaal is in talks to be cast in the Spider-Man: Homecoming sequel as antagonist Mysterio. The Mysterio name has been taken by four characters, though it’s not known which identity is planned for use. The character’s most iconic storyline was the mini-series Spider-Man: Mysterio Manifesto (2001) by Tom DeFalco, which featured Spider-Man teaming up with Daredevil (currently portrayed on Netflix by Charlie Cox). But since comic book film adaptations prefer to lift a variety of plot elements from numerous different stories instead of directly adapting one of them – and since Marvel’s Netflix shows have never been acknowledged in, or influenced any of, Marvel’s films – we probably shouldn’t expect to see Daredevil involved. That mini-series did, however, include Vulture, who – according to Variety‘s Justin Kroll – will be returning. So who knows?
Either way, if Gyllenhaal decides that he’s interested, and the current plan isn’t changed, then perhaps he’d prefer for his experience in the superhero genre to be as supporting characters or villains instead of leading heroes.