1) Jake Gyllenhaal
The actor who has come the closest to playing Spider-Man is surely Jake Gyllenhaal – though he almost got it in the strangest of scenarios.
While he was in the running for 2002’s Spider-Man, Gyllenhaal lost out to Tobey Maguire. However, by 2004’s Spider-Man 2, Maguire had severely injured his back while filming Seabiscuit and it was feared he would not recover in time for shooting.
In his place, Gyllenhaal was chosen to replace him (perhaps partly due to the fact he was dating Kirsten Dunst at the time). He even had a costume fitting, before Maguire’s back healed and the recasting didn’t come to pass. Shortly afterwards, he missed out on another role when he lost the part of Batman to Christian Bale.
Some actors just aren’t destined to be superheroes I guess.