What If Jake Gyllenhaal Had Become Spider-Man?

Once upon a time, Jake Gyllenhaal was almost Peter Parker. No, not before Tobey Maguire took the role in Sam Raimi’s original, charmingly dated 2001 Spider-Man. Gyllenhaal was one bad back away from taking over the role as the webslinger; he was the stand-by for Maguire, who was suffering some serious lower back issues during pre-production. Had Maguire not been able to go, Gyllenhaal would have stepped in. Thankfully, Maguire was able to carry on, but what if?

What if, out of nowhere, Spider-Man 2 starred Jake Gyllenhaal instead of Tobey Maguire? Switching the stars of a franchise can spell doom for said franchise nine times out of ten (I’m looking at you, Speed 2). Marvel films have become teflon in recent years, impervious to bad press, but in the early 2000s the empire was still being built in Hollywood. Despite the fact that Jake Gyllenhaal is a widely respected actor, even in 2004, changing the face of a film franchise after only one movie would have disrupted the continuity to the point where the film may have failed at the box office. And just think, the best Spider-Man movie we have gotten thus far might have been hard to watch objectively, without seeing Jake Gyllenhaal in every scene and think, “yeah, it’s not Maguire.” The distraction of such an epic upheaval would have been too much to overcome.

Spider-Man 2


Not only would a reboot of the Spider-Man franchise been a foregone conclusion, but a reboot may have happened much sooner.

Then again, if Gyllenhaal took over the role, we may not have had to sit through Spider-Man 3.

And what would have become of these two actors and their subsequent careers? The superhero film is a blessing and a curse for many actors not named Christian Bale, and perhaps Gyllenhaal wouldn’t have turned in some of his more brilliant performances in the upcoming years. Just one year after Spidey 2, Gyllenhaal earned a well-deserved Oscar nomination for his role in the tragic, heartbreaking Brokeback Mountain. While he did scuffle through films like Proof, Prince of Persia, and Love & Other Drugs, Gyllenhaal turned in great performances in Jarhead, Brothers (co-starring Maguire), and Zodiac.

Let’s stop there, before we get to Gyllenhaal’s recent run. Would Spider-Man ever have gotten a role in Zodiac? I content he would not, at least not in 2007, the same year Spider-Man 3 came out. Gyllenhaal would have definitely had a scheduling conflict, and he is the heart and soul of what is arguably David Fincher’s most mature, complete film to date.


Maguire did get through his back problems and complete Raimi’s Spider-Man trilogy, and then sort of disappeared after that turned out to be a disaster. Maguire’s star lost some shine it seemed, or perhaps he took some time off to separate himself from the Peter Parker albatross. Whatever the case, while Maguire was off the grid for the most part, Gyllenhaal has blossomed into one of the best actors working today. That is without a doubt. His performance as a quirky, tortured detective in Prisoners stole the film from Hugh Jackman in my opinion, and the fact that his wiry, disturbed turn in last year’s Nightcrawler missed an Oscar nomination is criminal. Now, with the rave reviews and hot anticipation for his boxing film Southpaw pouring in, perhaps Jake Gyllenhaal is in line for another flirtation with Oscar.

Pawn Sacrifice

Tobey Maguire, in the meantime, has finally resurfaced in Pawn Sacrifice, the drama surrounding chess master Bobby Fischer. While Maguire looks solid in the trailer, it’s been a while since anyone has considered Tobey Maguire one of the best of his generation. Perhaps if he hadn’t fixed his back, and maybe if he hadn’t reprised his role in 2004’s Spider-Man 2, Gyllenhaal would have suffered the wrath of Spider-Man 3 and disappeared for a few years.

Larry Taylor - Managing Editor
Larry Taylor - Managing Editor
Larry is the managing editor for Monkeys Fighting Robots. The Dalai Lama once told him when he dies he will receive total consciousness. So he's got that going for him... Which is nice.