How many actors have playedSpider-Man? We’ve had moreSpider-Manmovies than there are Baldwin brothers, or Kardashian sisters. But so what? Everybody loves the friendly neighborhood webhead! It’s been more than half a century since Amazing Fantasy #15 hit the stands and ever since Stan Lee and Steve Ditko gave us the kid who does whatever a spider can, Peter Parker’s popularity has covered the world like a spider spinning its web. (Ugh sorry).

The wise cracking, hard working, hard luck hero is a young actor’s dream. The number of guys who have wanted to get in that mask earned by Tobey Maguire, Andrew Garfield, and Tom Holland could fill aSpider-Versemovie packed with Miles Morales, Doc Ock, Spider-Gwen and every other comic version of the wall crawler. Here, we look at 10 Actors who were almost cast as Spider-Man. For whatever reason, they just didn’t make it into that costume.

10Tom Cruise

We should all be thankful that the Tom CruiseSpider-Manwas never made. This is no dig at Cruise’s acting chops. It’s just that we’re talking about the 1980s, decades before the critical and box-office badassery of the Marvel Cinematic Universe. Marvel Comics are filled with cinema quality stories, but for years, most attempts to get something made stalled in development hell. When movies did make it across the finish line, they tended to be cheesy disasters like 1990’sCaptain America. When the low rent production house responsible forMasters of the Universe,American Ninja, andSuperman IVgrabbed therights to Spider-Manfor less than a quarter million dollars, they went through several screenplays and directors, as they dreamt of luring Cruise. Thankfully, the Cannon Group lost the rights altogether after one of their checks to Marvel bounced shortly before cameras were set to roll.

9Charlie Sheen

During a 2012 appearance on Jay Mohr’s podcast, Charlie Sheen revealed that he’d once campaigned to play Spider-Man. He was a big deal at Orion Pictures, who had released his Oscar winning filmPlatoon. Sheen says he had an office there and pitched themSpider-Man, but they weren’t interested. “They said ‘comic books are not the future’ and I said, ‘But it’s Spider-Man, I’m perfect,'” he told Mohr. He didn’t have the rights, but he was looking to buy them. Orion filed bankruptcy in 1991.

8Edward Furlong

The production company responsible forRambo,Showgirls, andTerminator 2: Judgment Daywere ready to take a crack at Spider-Man in the early 90s, with James Cameron writing and directing. He was set to reunite hisT2star Edward Furlong with Arnold Schwarzenegger, who would have been Doctor Octopus, but Carolco went bankrupt beforeSpider-Mancould get made. Cameron moved on toTitanic. (Eddie’s comic book movie was 2005’sThe Crow: Wicked Prayer, with Tara Reid.)

7Leonardo DiCaprio

TheSpider-Manrights were next snatched up by Sony Pictures, who wanted to make something from the script James Cameron had developed at Carolco, but with hisTitanicstar in the lead.Leonardo DiCaprio, however, had other plans. He said no to suiting up as Spider-Man just as he’d said no to playing Robin inBatman Forever.

Andrew Garfield wasn’t the first English actor in the running to play New York’s web-slinging hero. Jude Law’s performance in 1999’sThe Talented Mr. Ripleyearned him an Oscar nomination for Best Supporting Actor and according to his reps, Columbia Pictures had made “some overtures” to him aboutSpider-Man. He was later offered the lead inSuperman Returns, but turned it down over the costume.

5Freddie Prinze Jr.

A report from Entertainment Weekly published in June 2000 mentioned DiCaprio, Jude Law, and Freddie Prinze Jr. as Spider-Man hopefuls, which by that point had Sam Raimi attached to direct. Several years after the fact, Prinze told Howard Stern that he was the studio’s first choice, but that Raimi lobbied Sony for Maguire instead. Hey, asStar Wars Rebelsfans know, at least Prinze got to be a Jedi, right?

4James Franco

James Franco co-starred in all three of Raimi’sSpider-Manfilms, as Peter Parker’s best friend. But he initially auditioned to play the lead, before he was ultimately cast as Harry Osborn, the son of the Green Goblin. It’s kind of like Cillian Murphy in theDark Knighttrilogy, who played the Scarecrow, but had auditioned to play Batman.

3Scott Speedman

Freddie Prinze Jr. wasn’t the only teen heartthrob to get close to the role. Scott Speedman, one third of the love triangle that drove J.J. Abrams’ teen TV soapFelicity, screen tested for Raimi. He later made his way into theUnderworldmovies.

2Jake Gyllenhaal

Did Tobey Maguire really throw out his back beforeSpider-Man 2? Or was it a negotiating tactic to get more money for the sequel, as was rumored at the time? Either way, Sony wasn’t screwing around. They hadJake Gyllenhaalwaiting in the wings. Maguire showed up for what became one of the best superhero movies ever. There was a sort of reference to this on TV’sEntourage, when “Gyllenhaal” replaced the show’s fictional A-lister in the show’sAquamanfranchise. (Directed, in the show, by James Cameron!).

1Josh Hutchinson

When Sony abandoned plans for a fourth entry in the Sam Raimi franchise and opted to reboot the character with music video director turned filmmaker Marc Webb,Josh Hutchersonwas one of the actors strongly rumored for the role. There’s even a kickass audition floating around online. While Andrew Garfield beat him forThe Amazing Spider-Man, Josh did just fine in a little series calledThe Hunger Games.