10 Actors You Won't Believe Almost Played Spider-Man

8. Jake Gyllenhaal

People like to joke that Tobey Maguire and Jake Gyllenhaal look enough alike that you can make a joke about them looking so alike (they even played brothers in a film called Brothers). Interestingly, though, Gyllenhaal very nearly ended up playing Spider-Man as a result of his look-alikeness. With Toby Maguire facing major health issues after his work on the underwhelming horse film Seabiscuit, director Sam Raimi prepared for the worst; he considered replacing his leading man with Jake Gyllenhaal for Spider-Man 2, out of fear for Maguire's life. Gyllenhaal was sent to Spider-Man boot camp as a result, and trained in the art of being a superhero with the genuine intention of stepping in for the Spidey sequel. In the end, Maguire recovered in time and Gyllenhaal wasn't needed anymore. Gyllenhaal took a role in The Day After Tomorrow instead, and Toby Maguire ended up in one of the best superhero flicks ever. For continuity's sake, we're glad Maguire recovered, though. Gyllenhaal would have been a good Spider-Man, probably, but he might also have been a little bit too cool for the role.