Oh, what might have been! Despite the fact that Spider-Man 2 went into production almost immediately after Spider-Man finished shooting, Tobey Maguire still managed to squeeze in a well-received turn in Seabiscuit. However, the actor hurt his back shooting that movie, and seeing as he was also looking for a raise of $4 million for the sequel, Sony came very close to recasting him. Their top choice? Jake Gyllenhaal. The tabloids at the time had a field day with this one because Gyllenhaal was dating Kirsten Dunst. They spun it so that it sounded like Maguire was being pushed out because the studio wanted Dunst's new boyfriend, but he recovered from that injury sooner than expected and ended up scoring a cool $17 million for returning. The sequel even referenced his injury in the scene which saw a powerless Peter fall from the sky and land on a car, complaining about his back as he limped away. That wasn't it for Gyllenhaal though. Years later when it looked like Maguire had decided against playing Spider-Man for a fourth time, his name once again started doing the rounds. While the movie eventually never came to pass, Maguire did sign on in the end, leading to the Southpaw and Nightcrawler star missing out on the role for a second time. Perhaps that's why he's never starred in a superhero movie? Doctor Strange and Suicide Squad's Rick Flagg are among the roles he's been considered for and seemingly passed on in recent years...