Tobey Maguire notably played Peter Parker in Sam Raimi’s Spider-Man trilogy but there were several other actors who had the chance at playing the famed web-slinger. The renowned horror director branched out into the superhero genre with 2002’s Spider-Man. The critically acclaimed film went on to launch a trilogy before Sony decided to reboot the franchise 2012 and again in 2017.
After James Cameron’s failed attempt of adapting Spider-Man for the big screen, Raimi finally got the ball rolling with Sony. Up to this point, the filmmaker was best known for his work on the Evil Dead trilogy and other horror projects. Raimi’s passion for the Marvel character led to his hiring which worked out for the studio. Not only did Raimi develop a hit series, but he also made an impact on Kevin Feige who carried what he learned from the director in shaping the MCU after becoming the president of Marvel Studios. It’s no surprise that Marvel is circling back to Raimi to direct Doctor Strange in the Multiverse of Madness considering his past success with the superhero genre.
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Maguire’s casting was one of the highlights of the Spider-Man trilogy and Raimi had a major hand in the casting process. The actor already had a handful of titles under his belt but he became one of Raimi’s top choices after his performance in 1999’s The Cider House Rules. Raimi had faith that Maguire could perfectly embody Peter Parker and his alter ego but the actor’s path to the role wasn’t so simple. The studio had many other actors in mind for the role and here’s everyone who had connections to the lead in Raimi’s Spider-Man movies.
Leonardo DiCaprio
Before Raimi took the reins of a Spider-Man live-action adaptation, James Cameron set out to develop a project based on the Marvel hero. He spent time in the mid-’90s to work on a script and even had talks with Leonardo DiCaprio about starring as Peter Parker. The actor previously worked with Raimi on the 1995 western, The Quick and the Dead. The discussions, however, never progressed and the project was ultimately dropped. When Raimi’s Spider-Man film got moving, the studio revisited DiCaprio as one of their top interests in portraying the lead. The actor didn’t feel ready to commit to a role like that and instead worked on the films, Catch Me If You Can and Gangs of New York.
Freddie Prinze Jr.
Freddie Prinze Jr. got much further along in the casting process considering he actually had a face to face meeting with Raimi. During the development stages for the first film, Prinze was already a Hollywood heartthrob for his recent roles in I Know What You Did Last Summer and She’s All That. He was a major fan of the web-slinger but unfortunately, the actor went off-topic and spent much of the meeting with Raimi talking about how much he liked Venom (who Raimi did not like) and sort of ruined the first part of his audition. Even though Sony had an interest in Prinze, Raimi moved on and Prinze found the gig of playing Fred in Scooby-Doo.
Heath Ledger
When it came to the superhero genre in the ’00s, Heath Ledger’s sinister portrayal of the Joker in The Dark Knight stood at the top in terms of performances. The role garnered numerous awards for the late actor but he nearly played a superhero before taking on the role of the infamous villain. Not only was Ledger considered for the role of Bruce Wayne for Batman Begins but he was approached to play Peter Parker for Raimi’s film. Ledger decided to turn down the offer to audition since he felt like he would be taking someone else’s dream away. If he did play Peter, he most definitely wouldn’t have ended up as the Joker a few years later.
James Franco
Before James Franco was cast as Harry Osborn in 2002’s Spider-Man, the actor screen-tested for the role of Peter Parker. Up to this point, Franco had starred in Freaks and Geeks and only a handful of film roles. The actor made it far in the audition process but wasn’t deemed the perfect fit to play the titular character much to his dismay. That said, he clearly made an impression because he was offered the role of Peter’s best friend and roommate. Over the course of the franchise, Franco’s role took a more exciting turn since he became the second Green Goblin.
Wes Bentley
Wes Bentley is now an experienced actor but when Raimi’s Spider-Man was casting, he just didn’t feel ready to take on an A-list type of role. The actor was coming off of the success of his role in Sam Mendes’ American Beauty. Bentley’s performance led to a number of big auditions, including that of Peter Parker, but the timing just wasn’t right. Losing out on the gig didn’t completely end his opportunity at playing a Marvel character since Bentley ended up playing Blackheart in 2007’s Ghost Rider.
Josh Hartnett
Similar to Wes Bentley’s situation, Josh Hartnett also turned down the chance of playing Spider-Man due to the professional fears it would bring. Hartnett worried that it would be a defining role in his young career and he wasn’t emotionally prepared. The actor has stated that he additionally rejected offers to audition for other superheroes like Batman in Batman Begins and Superman in Superman Returns.
Chris Klein
After appearing in the 1999 comedic hit American Pie, big studios took notice of Chris Klein. He attracted the likes of Sony who screen-tested him for the role of Peter Parker. It’s not clear how far Klein got in the audition process but he ultimately didn’t get the part. His career continued to evolve and even though he never got a chance at playing a Marvel character, Klein did get a chance at a DC figure. He portrayed the protagonist Cicada in The Flash season 5.
Scott Speedman
Scott Speedman was another up-and-coming young actor who went through rigorous screen-testing for 2002’s Spider-Man. The actor was best known for his time on Felicity which led him to opportunities for once in a lifetime film roles. Speedman lost out on the role but he found a breakout film role elsewhere. In 2003, Speedman starred in Underworld and the 2006 sequel.
Jake Gyllenhaal
Jake Gyllenhaal originally lost out to Tobey Maguire the first time around but the actor had a second shot after Spider-Man made its debut. Before filming for Spider-Man 2 began, Maguire injured his back on the set of Seabiscuit. The injury was severe enough to force the studio into making replacement plans in case Maguire couldn’t reprise his role. Gyllenhaal went into negotiations to take over the role but Maguire made a full recovery just in time. Coincidentally enough, Gyllenhaal ended up playing the antagonist Mysterio in 2019’s Spider-Man: Far From Home opposite Tom Holland.
