• Jake Gyllenhaal was considered to replace Tobey Maguire as Spider-Man due to an alleged back injury and tense negotiations for Sam Raimi’s sequel in 2004, but Maguire did return for Spider-Man 2 and 3.
  • Jake Gyllenhaal nearly played Bruce Wayne in 2005’s Batman Begins from Christopher Nolan and got far in the casting process, but Christian Bale ultimately got the role.
  • Gyllenhaal’s biggest superhero role thus far has been as the villain Mysterio in Spider-Man: Far From Home, though he could still play a superhero in the near future.



Although actor Jake Gyllenhaal has yet to play a major superhero on the big screen, he almost played two of the biggest heroes in the early 2000s. Within two years of each, Gyllenhaal nearly became a live-action Spider-Man and a new live-action Batman. Although he didn’t get either of the hero roles, the stories behind the missed opportunities are rather interesting, along with the potential for Gyllenhaal to perhaps claim a superhero role very soon.

Currently, Jake Gyllenhaal is one of a few popular names to play the next live-action Batman. Although Robert Pattinson is currently playing a younger Batman closer to the start of his career in Matt Reeves’s ongoing trilogy, The Brave and the Bold and its presumably older Batman will be connected to the greater DC Universe reboot. Keeping that in mind, here’s how Jake Gyllenhaal lost out on two major superhero roles in the early 2000s, and what it’s led to in the years since.


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Why Jake Gyllenhaal Almost Replaced Tobey Maguire As Spider-Man (But Didn’t)

Maguire Almost Didn’t Return for Spider-Man 2

Tobey Maguire's young Peter Parker in Spider-Man suit

Following Tobey Maguire’s debut outing as Peter Parker in 2002’s Spider-Man from director Sam Raimi, there was a season in which Maguire might not have returned for 2004’s Spider-Man 2. Citing a preexisting back injury following the first film that was allegedly exacerbated during the filming of 2003’s Seabiscuit, negotiations for Maguire’s Spider-Man 2 return were somewhat tense between the actor’s team and Columbia Pictures. This was ultimately a negotiating tactic on the part of Maguire’s team, though Columbia called their bluff with plans to have Jake Gyllenhaal replace Maguire for the Spider-Man sequel.

Spider-Man 2

After defeating the Green Goblin, Tobey Maguire’s Spider-Man struggles with self-doubt in both his superhero career and his personal life. But when Alfred Molina’s Doctor Octopus threatens Peter Parker’s loved ones, the web-crawler must stay true to his heroic purpose and don the mask once again in this second installment of Sam Raimi’s Spider-Man trilogy.

Release Date
June 30, 2004

Alvin Sargent

Donna Murphy , Alfred Molina , Tobey Maguire , James Franco , Rosemary Harris , Kirsten Dunst

127 minutes


$200 million

Of course, Tobey Maguire did return for Spider-Man 2 as well as 2007’s Spider-Man 3, as his team was able to smooth things over with Columbia. Likewise, Jake Gyllenhaal has since confirmed he was considered to replace Maguire as Spider-Man (among others) following concerns about Maguire’s back injury (exaggerated or otherwise). All things considered, it certainly would have been bizarre to have seen Gyllenhaal take the reins as Spider-Man from Maguire for the next two movies in Raimi’s trilogy, though the recast would have made sense considering the actors’ passing resemblance.



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Jake Gyllenhaal Lost The Batman Role In The Dark Knight Trilogy To Christian Bale

Gyllenhaal Got Pretty Far In The Casting Process

Christian Bale standing in front of the Batman suit in The Dark Knight

Not long after the missed opportunity to play Spider-Man, Jake Gyllenhaal nearly played Batman in 2005’s Batman Begins from director Christopher Nolan, the start of the beloved and legendary Dark Knight trilogy. Offering a more grounded take on the Caped Crusader, multiple actors were considered for the role before Christian Bale was ultimately cast to play Bruce Wayne’s Batman. This includes Jake Gyllenhaal, and there are indications that he got quite far in the casting process.

Maggie Gyllenhaal (Jake Gyllenhaal’s sister) was cast as Rachel Dawes in 2008’s
The Dark Knight
, replacing Katie Holmes in
Batman Begins

Recently, Gyllenhaal confirmed in an interview with Variety that he received a personal call from Nolan himself to let him know that he didn’t get the role, while also confirming that he got very close to becoming the next live-action Batman of the 2000s. However, it does mean that the door is still open for Gyllenhaal to play the next Batman in the upcoming DC Universe reboot. With the reveal that this Batman will have his biological son Damian as his current Robin, Jake Gyllenhaal would be the right age to bring this new version of Caped Crusader to life.

Batman Begins

Christopher Nolan’s take on Batman’s origin story sees Christian Bale take up the mantle of the Caped Crusader. Batman Begins follows young Bruce Wayne who, reeling from the murder of his wealthy parents, decides to become a vigilante in order to save Gotham City. This pits him against the mysterious League of Shadows, an organization intent on destroying Gotham with the help of the villainous Scarecrow and his powerful fear toxin.  

Release Date
June 10, 2005

Warner Bros. Pictures

Warner Bros. Pictures

Ken Watanabe , Liam Neeson , Gary Oldman , Tom Wilkinson , Linus Roache , Christian Bale , Katie Holmes , Mark Boone Junior , Michael Caine , Rutger Hauer , Cillian Murphy , Morgan Freeman

2h 20m

150 million

Jake Gyllenhaal Eventually Joined The MCU As A Major Spider-Man Villain

Mysterio In Spider-Man: Far From Home

As it stands, Jake Gyllenhaal’s biggest role in the superhero movie genre was in 2019’s Spider-Man: Far From Home where he played Quentin Beck’s Mysterio, a Spider-Man villain who attempted to make the world believe he was the world’s next big hero though advanced illusion technology. Before his demise at the end of Far From Home, Mysterio also exposed Spider-Man’s secret identity as Peter Parker to the entire world. That said, it seems as though it’s only a matter of time before Jake Gyllenhaal finally becomes a movie superhero following his missed opportunities in the early 2000s.

Spider-Man Far From Home Poster-1

Spider-Man: Far From Home

Following the events of Avengers: Endgame, Spider-Man: Far From Home follows Peter Parker (Tom Holland) as he deals with the fallout of Thanos’ snap and the weight of Tony Stark’s legacy in a post “blip” world. Peter and his friends go on summer vacation to Europe, where Peter finds himself suddenly the inheritor of Tony’s incredible tech. However, the trip suddenly goes awry as Europe comes under siege from otherworldly villains, routed by a cloaked hero, Mysterio. Partnering with Nick Fury, Maria Hill, and Mysterio, Peter will fight to protect his friends while figuring out his place in a post-Iron man world. 

Jon Watts

Release Date
July 2, 2019

Marvel , Sony


Erik Sommers , Chris McKenna

Michael Keaton , Tom Holland , Jacob Batalon , Jon Favreau , Zendaya , Samuel L. Jackson , Martin Starr , Marisa Tomei , Cobie Smulders , Jake Gyllenhaal , Tony Revolori , Angourie Rice

129 minutes

Spider-Man: No Way Home

$160 million

Key Release Dates

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