Spider-Man is one of the most iconic superheroes to ever hit the big screen. Many actors have played Spidey over the years, in live-action, voiceover, and television shows. Everyone has their own assertions about who wore the Spidey suit best, but popular opinion seems to suggest Tom Holland may be everyone’s favorite iteration of the famed web-slinger (so far). It was Tobey Maguire, however, who made history when he starred as your friendly neighborhood Spider-Man in the first-ever big-budget Hollywood film based on the Marvel comic book character. Maguire also reprised his role for Spider-Man: No Way Home.
That said, there was a time when Maguire almost lost the coveted role to Jake Gyllenhaal. Ironically, years later, Gyllenhall would go on to star as Mysterio in Spiderman: Far From Home. After salary negotiations between Sony and Maguire’s camp went awry, Sony entertained other actors to replace Maguire, including Gyllenhaal. Here is how Jake Gyllenhaal almost played Spider-Man.
Salary Negotiations Gone Wrong
After starring in Sam Raimi’s Spider-Man in 2002, Maguire quickly became a big Hollywood star. His next project was the critically acclaimed Seabiscuit, a Depression-era underdog story about a discounted racehorse who, with training and dedication, became the greatest thoroughbred of all time. Maguire plays Red Pollard, the jockey that rode Seabiscuit to fame in the 1930s. Maguire had previously gained weight and muscle mass for his role as Spidey, but had to lose much of it during his transformation into Red Pollard. Moreover, the role was very physically demanding. Maguire told The Racing Post: "I was working out and getting really strong and losing a lot of weight, but when you get on a real horse, it's a whole different deal," he said. "You're using all the stabilizing muscles in your legs and balancing on the balls of your feet on this 1,200-pound elite athlete."
Maguire also reportedly had a pre-existing back injury that made stunts difficult. After his role in Seabiscuit came to an end, Raimi was ready to begin shooting for Spider-Man 2. According to a 2003 report by Variety, Maguire felt he wasn’t being properly compensated for the sequel, and his team had issued the following statement after a meeting with Raimi discussing the future of the franchise. “After doing two physically demanding films in a row, Tobey has experienced mild discomfort in his back which is in the final stages of healing. With an April 12 start date around the corner, everyone involved wants to be certain he is able to do the intense stunts.” Columbia Pictures (a division of Sony) got the impression Maguire was using his existing back condition as a salary-negotiation tactic and was not about to push back its 2004 release.
Sony Called Maguire’s Bluff
Columbia Pictures made the difficult decision to recast Maguire for Spider-Man 2 (and onward) and began to court other actors for the role, one of them being Gyllenhaal. According to L.A. Times, Sam Raimi stated, “I didn’t want to do something so irresponsible that I’d regret it for the rest of my life,” about casting Maguire in a role that could be damaging to his physical health. While negotiations were in the works with the new Peter Parker, Maguire's representatives went on damage control. Maguire’s team, with the help of Universal Chief Ron Meyer (his then-girlfriend’s father), were able to eventually salvage his role as Spider-Man and smooth things over with the studio, as long as Maguire was willing to submit to extensive medical tests proving he was fit enough to handle the role.
According to a 2003 interview with the Los Angeles Times, Maguire had time to reflect on the situation and believes it could have been handled differently. “I feel like I learned a lesson,” he says. "The movie is the most important thing. I’m glad I got to look these people in the face and say, ‘I’m really sorry. I’m going to do whatever it takes.’" Spider-Man 2 would go on to become a massive box office success and is commonly referred to as the best superhero movie of all time. Maguire would see his salary for the sequel increase from the $4 million payout from Spider-Man to $17 million for Spider-Man 2.
Jake Gyllenhaal’s Perspective
When asked by Yahoo! about the potential casting during 2019 promotions for Spider-Man: Far From Home Gyllenhaal had this to say: “I heard the same thing. The truth of the matter is, in the end, [Tobey Maguire is] Spider-Man. There are so many roles in my career where I was up against another actor, or there was something happened that possibly could’ve happened but didn’t happen but maybe it would have. Eventually, my belief is when an actor’s played a character, particularly in a movie, the character’s theirs, and that’s that. But yeah, there was talk, he hurt himself and there was talk. There was a slew of actors [possibly up for the part], and I was one of them.” Interestingly enough, Gyllenhaal would eventually star as villain Mysterio opposite Tom Holland's Spider-Man. While we are curious to see what Gyllenhaal would have brought to the role, ultimately, Maguire would go on to star in the next two movies in Sam Raimi's Spider-Man trilogy.