Sam Raimi Almost Replaced Tobey Maguire in Spider-Man 2 With an Actor Who Became an MCU Villain

Here is a fun bit of franchise backstory that still blows my mind: the guy who almost replaced Tobey Maguire as Spider-Man ended up playing one of Peter Parker's trickiest enemies years later. And honestly, it kind of changed him.

Raimi nearly swapped Tobey for Jake on Spider-Man 2

Back when Sam Raimi was gearing up for Spider-Man 2, he heard something scary: if Tobey Maguire aggravated his back during a stunt, the damage could be catastrophic. Raimi says he couldn't risk that on set, and he couldn't make a Spider-Man movie with Peter sitting out the big action. So he started eyeing Jake Gyllenhaal to step in.

'I couldn't ask him to do anything where that tragedy could happen on the set, so at the same time, I couldn't compromise the movie and not have Peter Parker take such an active role in all these scenes. So I had to call Tobey and say, 'Tobey, from what I hear, I can't work with you in the movie.''

In the end, Raimi brought Maguire back with extra safety precautions, and history unfolded the way we know it. But that brush with recasting set the stage for something else down the line.

Gyllenhaal finally joined the web anyway — as Mysterio

Jake Gyllenhaal eventually swung into the MCU as Quentin Beck, aka Mysterio, in Spider-Man: Far From Home. Fans loved the push-pull with Tom Holland — allies one minute, adversaries the next — and Gyllenhaal made the performance pop with a mix of relaxed showmanship and that Brokeback Mountain intensity.

More interesting: he says the role rewired how he thinks about these movies and about acting in general.

'It was such a cathartic thing to be able to throw away all that seriousness and really become the actor that I think I've always wanted to be... I think that we go through journeys in our life where we're finding ourselves, and in the case of Spider-Man, I think I realized 'hey, acting is really fun, you know, enjoy it!''

You can feel that looseness in Far From Home — it makes Mysterio more layered than a straight-up mustache twirler.

Should Mysterio be back for Spider-Man: Brand New Day?

If anyone has unfinished business with Peter, it's Mysterio. Without him tipping off Peter's identity, a lot of the trouble that followed doesn't happen. After the multiverse chaos of No Way Home, bringing Beck back for a reckoning makes sense — push Peter, see what breaks, and what doesn't.

There are also rumblings that the next movie won't be a single-villain story. Michael Mando's Scorpion has been floated, which points toward a Sinister Six-style lineup — and Mysterio is traditionally one of that crew's key players.

Even if it isn't Gyllenhaal's exact version, some chatter suggests a different spin on the character. For the record: in the comics, Mysterio is a special-effects and illusion guy, not an actual sorcerer. If the movie goes full mystic with him, that would be a new twist rather than a straight comic lift.

What we're hearing about Spider-Man: Brand New Day

• Title: Spider-Man: Brand New Day
• Director: Destin Daniel Cretton
• Major cast: Tom Holland, Zendaya, Jacob Batalon, Jon Bernthal, Michael Mando, Sadie Sink
• Production companies: Columbia Pictures, Marvel Studios, Pascal Pictures
• Release date: July 31, 2026

Do you want Jake Gyllenhaal back as Mysterio, or are you curious to see a new take under the fishbowl?

Spider-Man: Far From Home and Spider-Man 2 are streaming on Disney+ in the US.