In the early 2000s, actor Jake Gyllenhaal lost out on two major superhero roles, one from Marvel Comics with Spider-Man and DC with Batman.

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.

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

Maguire Almost Didn’t Return for Spider-Man 2

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.

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.

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

Gyllenhaal Got Pretty Far In The Casting Process

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.

Note: 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.

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.