With four big-screen franchises spread across the last 17 years, much has been made about the sheer number of Spider-Men who have made their way to theaters. On the live-action front alone, theater-goers have seen Tobey Maguire, Andrew Garfield, and Tom Holland don the suit, and each has offered a unique spin on Peter Parker and his masked counterpart, for better or worse. The story of Spider-Man on screen is a wild one, and the names which have been thrown out for the role of Spider-Man range from unlikely to pop stars, to A-list leading men, to actors who have ended up in Spidey films in a different capacity altogether.
10 Jake Gyllenhaal
Following the success of Spider-Man, a sequel was inevitable, but the involvement of the first film's Peter Parker, Tobey Maguire, was not. After sustaining multiple injuries and discomforts on both the first film and the horse racing drama Seabiscuit, Maguire was reluctant to take on another stressful shoot. Faced with the possibility of losing their leading man, Sony immediately started looking for possible replacements. Enter Jake Gyllenhaal...
Although Gyllenhaal had seen his fair share of success with films such as October Sky and Donnie Darko, he was not the household name that he is today. Eventually, Maguire agreed to return with the help of a hefty payday, and 16 years later Gyllenhaal would get to experience Spider-Man when he took the role of Magneto in Spider-Man: Far From Home.
9 Leonardo DiCaprio
Before Tobey Maguire got his chance to play Spider-Man, his real-life friend Leonardo DiCaprio confirmed that he was once in the running for Maguire's role in Spider-Man. Although the studio wanted the Titanic star to dawn the red and blue tights, DiCaprio wasn't interested in taking the role, one which he had been rumored for years earlier for a different.
DiCaprio's name also came up alongside Edward Furlong's as a possible Parker in relation to an unproduced James Cameron Spider-Man film, a film which would have seen him take on bodybuilder-turned-actor-turned-politician-turned-actor Arnold Schwarzenegger as Dr. Octopus. Ironically, it was Titanic that would derail the project before it ever officially began.
8 Tom Cruise
In the late 80s, Cannon films, a company for their low budget sequels to established franchises, bizarre original films, and eccentric bosses, was planning on making their own version of Spider-Man. If that wasn't ambitious enough, they were looking to cast Tom Cruise, who was already a big name thanks to his successful run of movies in the mid-to-late 80s.
Given Cannon's record, including their attempts to revive the original Superman franchise, the movie would have almost certainly been a disaster, but the idea of a young Tom Cruise slinging webs against Bob Hoskins's Dr. Octopus is an intriguing one, to say the least.
7 Heath Ledger
Although the late Heath Ledger is now synonymous with his own iconic turn in the superhero genre as Joker, years earlier he was in the running to play the role in the original Raimi film. Fresh off his name-making turn in 10 Things I Hate About You, casting a teen heartthrob in the role would have been a no-brainer, but it may not have fit the outcast status that Peter Parker is known for.
Still, one cannot help but think that Ledger would have put a believable, unique twist on the character had he taken on the role. Although he was taken far too early, his short career showed us that he could take on nearly any role that was thrown in his direction.
6 Freddie Prinze Jr.
Much in the same vein as Ledger's involvement, Prinze Jr. has claimed that he was in the running for the role that became Tobey Maguire's. He was a mainstay in teen comedies and dramas throughout the late-nineties and early-aughts, and Peter Parker would have been right up his alley if they had been going for that type of movie.
Much like Ledger, Prinze's status as a heartthrob may not have worked for those who wanted Parker to be the geeky outcast. It is a far cry from the high school pretty boy that Prinze would make a name of. Thankfully, Sony went in a different direction
5 Josh Hutcherson
Around the same time he became a household name in the Hunger Games movies, Josh Hutcherson was looking to play Spider-Man in the Marc Webb films, even auditioning for the role. Hutcherson was not done clamoring for the role after he became a bigger name. When the Webb movies were done, Hutcherson wasted no time using his bigger status to clamor for the role that eventually went to Tom Holland
Hutcherson would have been an interesting choice to play Spider-Man. Although older than Holland, he has the boyish looks and the chops to play the more youthful take on Spider-Man that the current series brings. His time has more-than-likely passed, however, but if Holland leaves, history tells us Hutcherson will be there waiting.
4 Timothee Chalamet
The Call Me By Your Name actor was not yet a household name when the audition process began for the MCU's Spider-Man. According to the actor, however, his chance at the role was gone as soon as it started, as he claims to have botched the audition process. This may have been a blessing in disguise, however.
Now that Chalamet is a big-name actor of a different type, one might say that his role of Spider-Man may have prevented him from getting roles like his recent slew of acclaimed performances. It is clear that he has the talent, but perhaps Spider-Man wasn't the right place to display it.
3 Donald Glover
While still making a name for himself as a writer and comedian on Community, Donald Glover fans clamored for him to be the first Spider-Man of color. While there was never any confirmation of his name being attached to any of the films that came afterward, it was a rumor and desire that gained enough traction for him to address it in his stand up comedy.
Aside from becoming a superstar of comedy, television, and music since then, the fan-driven support for this idea has made Glover part of the Spider-Man canon in a pair of ways. First, he voiced Miles Morales in Disney XD's Ultimate Spider-Man. Then, when Spider-Man joined the MCU, Glover had a small role as Miles's uncle Aaron in Spider-Man: Homecoming.
2 Charlie Sheen
If the notably eccentric Charlie Sheen is to believed, he was going to play Spider-Man in a franchise he was planning in his own head. During an interview with comedian and podcast host Jay Mohr, Sheen claimed that, while he was working for Orion, he was trying to convince the higher-ups to get a Spider-Man project off the ground before he was too old to participate. They declined, seeing no future in the superhero genre.
Although Sheen makes more headlines off-screen now, the idea of him headlining a superhero blockbuster in his younger days isn't entirely ridiculous. He was a renowned young actor who was getting big roles across all genres. Unfortunately for Sheen, all we have are thoughts of what could have been.
1 Michael Jackson
Yes, that Michael Jackson. More the product of the pop star's own desires than any filmmaker's, Jackson had a plan that would let him be Spider-Man on the big screen. He was going to buy Marvel then cast himself as Peter Parker in the upcoming movie. It was a rumor that was confirmed by Stan Lee in 2009.
Michael Jackson wasn't a complete stranger to acting. His music videos were often short movies, he did star in the film The Wiz, and he had a cameo in Men in Black 2. However, taking away everything we know about the singer, the idea of him web-slinging across New York well into his thirties or forties is downright comedic.