More than a decade after nearly nabbing the superhero role himself, Jake Gyllenhaal is in talks to join the Spider-Man franchise. The actor is reportedly circling the role of Mysterio, a classic Peter Parker nemesis, in the Spider-Man: Homecoming sequel, according to The Hollywood Reporter.
Its a full-circle moment for the Oscar-nominated actor, who was once in line to play Spider-Man himself. This was back in 2003, when then-franchise star Tobey Maguire was rumored to be leaving the series, due to the physical toll it had taken on him—prompting the studio to meet with potential stars who could essentially Aunt Viv the next installment of the blockbuster-superhero series. One of those potential stars was Gyllenhaal, who was then a rising name thanks to his turns in critically acclaimed films like Donnie Darko and classic Oscar bait like Bubble Boy. He also happened to be dating Spider-Man star Kirsten Dunst at the time (imagine the adorable press tour that might have been!) and has said himself that people frequently mistook him for Maguire. It was going to be a classic Hollywood fix! But then Maguire came back to the franchise after all, while Gyllenhaal was forced to figure out a different path to bankable movie stardom. (Dont cry for him; he did just fine.)
Spider-Man wasnt Gyllenhaals only brush with the superhero realm. He also auditioned for the role of Batman in Batman Begins, a part that ultimately went to Christian Bale. The actor has remained fairly zen about those lost parts, telling the Daily Mail in 2015 that he was “open” to both roles, but readily accepted that they ultimately went to other stars. “I neither rue nor am I thankful for having not worked on these superhero films,” he said, diplomatic phrasing that twists the tongue.
Regardless, the Spider-Man: Homecoming sequel will be Gyllenhaals first foray into the world of franchise films since the ill-fated 2010 film The Prince of Persia. He learned his lesson since then, and has instead kept busy with dark indies and gritty dramas like Nightcrawler and Okja—building a reputation as a movie star with prestige acting chops. But he couldnt outrun the superhero movie machine for long. Now, much like Donald Glover—who joined Homecoming after the “Donald for Spider-Man” campaign—Gyllenhaal gets to enter the comic-book realm it in his own karmic way.
Get Vanity Fairs HWD NewsletterSign up for essential industry and award news from Hollywood.Full ScreenPhotos:The Royal Wedding: Dresses, Hats, and MoreYohana DestaYohana Desta is a Hollywood writer for VanityFair.com.
[contf] [contfnew] 
Vanity Fair
[contfnewc] [contfnewc]
