There is a moment in the bizarre 2002 cult classic Donnie Darko when Jena Malone as Gretchen tells the title character (played by Jake Gyllenhaal) that his name sounds like “some sort of superhero,” to which he replies, “What makes you think I’m not?”
Ironically, the future Oscar nominee would later be mentioned as a potential superhero movies star for years (once being considered for Spider-Man, and for Batman another time) before finally joining the Marvel movies in 2019 as the villain of Spider-Man: Far From Home, Mysterio. As cool as it was to see him in the MCU, I cannot help but wonder what could have happened if the DC movies got to him first, which is why I have compiled a list of characters I have in mind for him to play, such as one with similarly transformative talents.
I loved Jake Gyllenhaal’s performance as Mysterio in Spider-Man: Far From Home and the clever creative liberties the film took with the character. However, the Spider-Man villain I personally would have thought to cast him as is the Chameleon, particularly for how far the actor has gone to alter his own appearance for a role - like he did for Nightcrawler in 2014. Luckily, there is also a well-known DC baddie who fits that same description.
Basil “Baz” Karlo wanted to be the kind of actor who could become anyone - a dream that would eventually come true for him in the most nightmarish way possible after gaining the ability to shape himself into any person or thing, but at the cost of a body made entirely of a clay-like substance. Clayface is one of the most unique and recognizable Batman villains, but he has yet to be portrayed in a live-action feature film. Jake Gyllenhaal would make that debut count.
Speaking of Batman, I would also be curious to see the outcome of an alternate reality in which Jake Gyllenhaal became the lead of The Batman instead of Robert Pattinson in the end. Of course, there is still a chance that he could get a role in the Batman movies by playing another wealthy orphan and friend of Bruce Wayne with a secret vigilante alter ego.
For eight years, Stephen Amell played Oliver Queen on Arrow - one of the most popular DC TV shows ever, and the catalyst for The CW’s Arrowverse - until the character (and series) reached a bittersweet end. With that being said, I cannot think of a better time for the Green Arrow to finally make the transition into live-action cinema, whether that means getting his own solo movie or a supporting role in someone else’s flick. I believe Jake Gyllenhaal has the talent to give this character a stunning big screen introduction, as well, and I am not the first to suggest the idea either.
Another character who could be a great alternative to Batman is Owlman. Why? Because (depending on which version of the character you are referring to) he is essentially an alternate version of the Dark Knight from another reality in the DC Multiverse, but with a more sinister agenda (keep note of that fact that owls are known to prey on bats).
Batman and Owlman once crossed paths in the 2010 DC animated movie Justice League: Crisis on Two Earths, which saw the Dark Knight (voiced by William Baldwin) and his morally bankrupt doppelganger (voiced by James Woods) engage in a fierce conflict that I would actually love to see adapted for live action. Considering how Warner Bros. is starting to play around with interdimensional crossovers (both Michael Keaton and Ben Affleck play Bruce Wayne in the Flash solo movie), this is not such a far-fetched idea. Just putting Jake Gyllenhaal side by side with Robert Pattinson is enough evidence I need to know he would be the right choice.
On the other hand, there are plenty of other DC characters Jake Gyllenhaal could play who would give him the chance to mess around with the flow of time - much like he did in Donnie Darko and the Prince of Persia movie from 2010. In fact, there is one time-hopping DC hero whose big screen debut has been a subject of anticipation for quite a while.
A film featuring the attention-seeking, time-traveling businessman Michael Carter, otherwise known to DC Comics readers as Booster Gold, has apparently been in development for a long while, but to no avail as of late. Perhaps if Warner Bros. cast Jake Gyllenhaal in the role (which would be a great and rare opportunity for the Bubble Boy star to flex his comedic muscles, too), that could help speed up the process.
A character whose whole gimmick is also related to time is Hourman. The alter ego of chemist Rex Tyler (in the superhero’s first incarnation, at least) gets his name from a special pill he developed which imbues him with amazing abilities (including super strength, night vision, and underwater survival), but only for an hour at a time.
Some fans should already recognize Hourman from the Arrowverse series Stargirl - in which Rex Tyler’s son, Rick (Cameron Gellman), takes up the mantle after the death of his father (Lou Ferrigno Jr.) - and also might have heard that the hero recently had his own solo movie greenlit. The character is currently uncast, but given Jake Gyllenhaal’s previously mentioned experiences with time management in past performances, he would likely nail the emotional strain that must cause for the character.
Another type of character (or type of genre, I should really say) that Jake Gyllenhaal has taken on a few times in his career is the western - namely with the Oscar-winning 2005 romance Brokeback Mountain and with the underrated drama The Sisters Brothers (also starring John C. Reilly and Joaquin Phoenix in the title roles) from 2018. However, neither of those otherwise acclaimed films allowed the actor to show his potential for being an action star.
Thus, if he intends to return to the Old West, I recommend taking the lead on a reboot of Jonah Hex, the 2010 flop starring Josh Brolin as a horrifically scarred, Confederate Civil War veteran with the ability to talk to the dead. I do not think Brolin would mind seeing someone else play the role he originated for live-action on the big screen again, especially with a trusted actor like Jake Gyllenhaal.
If Jake Gyllenhaall ends up not having a future in the DC movies, I think I could live with that - especially given the rumors that we have not seen the last of Quentin Beck in the MCU, after all. However, if he were to make the transition from Marvel to DC (and vice versa) that many other actors so gracefully have, which character do you think would be the best match?
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Jason has been writing since he was able to pick up a washable marker, with which he wrote his debut illustrated children's story, later transitioning to a short-lived comic book series and (very) amateur filmmaking before finally settling on pursuing a career in writing about movies in lieu of making them. Look for his name in almost any article about Batman.