Edward Furlong as Spider-Man
You can thank financial issues for denying us the chance to see Eddie Furlong in the red and blue spandex in the mid-90s - not to mention Arnold Schwarzenegger as Doctor Octopus. Getting Spider-Man to the big-screen became even more of a tangled web after the collapse of Cannon. The rights ended up at Carolco Pictures, at the bequest of James Cameron, who wanted to write and direct a big blockbuster.
Carolco produced Terminator 2: Judgment Day, and then planned to collaborate with Cameron again on Spider-Man. Cameron's initial reworking of an existing script again featured arch-nemesis Doc Ock as the adversary. Having worked frequently together, Schwarzenegger was Cameron's first choice for the villain, and Furlong (the original John Connor) was strongly considered for the hero.
Cameron also wrote a more adult ‘scriptment’, with Electro and Sandman replacing Doc Ock. Cameron's bid to make Spider-Man is featured in the Rebecca Keegan book, The Futurist: The Life and Films of James Cameron.
In 1996, Carolco followed Cannon into that big studio heaven in the sky and left the Spider-Man movie in development hell. The company’s collapse proved the deathknell for Cameron's vision for the web-slinger, though parts of his script did make it to Sam Raimi’s adaptation almost a decade later.
Cameron managed to jump ship and make Titanic. Schwarzenegger and Furlong didn’t fare so well. While Arnie had the dubious honor of playing Mr Freeze (in Batman and Robin), Eddie simply went cold and his career faded. Though he will be seen alongside Seth Rogen in the upcoming The Green Hornet.
Leonardo DiCaprio as Spider-Man
MGM got its hands on the Spider-Man rights from Carolco, but following much legal wheeling and dealing, traded them to Sony Pictures in 1999 for the James Bond rights. Maybe MGM thought it was a poisoned chalice?
Sony got to work right away on making Spider-Man via Columbia Pictures, using Cameron’s script treatment, but not the director himself. The company also wanted to get its hands on the star of Cameron’s record-smashing Titanic, Leonardo DiCaprio, for the prize role of Peter Parker. Freddie Prinze Jr and Jude Law were also believed to be early contenders.
In the end, only Cameron’s idea for ‘organic web-shooters’ survived the many rewrites by David Koepp and then Scott Rosenberg, and DiCaprio’s body of work remains bereft of a superhero role. Self-confessed "Spider-Man nut" Sam Raimi was hired to direct, and Scott Speedman, Jay Rodan and James Franco were among those who tested for the lead.
Raimi ultimately got his man Tobey Maguire, despite the studio’s initial reluctance to cast him because of his small stature. Maybe they had reservations about the actor after watching Wonderboys and seeing him in bed with another future superhero, Robert Downey Jr?
The rest, as they say, is history - and, despite a dodgy third entry, Raimi and Maguire’s Spider-Man trilogy is the most successful superhero franchise in history (so far). Tell me again, why are they planning a reboot?