28. Doctor Octopus

It began with a slap to the face. Spider-Man was feeling pretty confident early in his career, when he first encountered Otto Octavius, a scientist whose invention of robotic arms had become fused to his body - in an accident that also took his sanity. Very quickly, Spider-Man learned that the heavyset man with poor eyesight was not to be underestimated, and in a memorable moment, Dr. Octopus grabbed Spider-Man with his mechanical limbs and effortlessly subdued the young superhero - and then slapped him hard in the face with his very human hand. Tossing Spider-Man aside (and out a window) like he was absolutely nothing to him, Dr. Octopus instantly had a physical and mental impact on his foe and this encounter led to Spider-Man's first real occasion of self-doubt and fear, so shaken was Peter Parker by this encounter with a villain who truly was his match.

Along with Green Goblin and Venom, Doctor Octopus has secured his place as one of Spider-Man's greatest and most dangerous foes. From organizing the Sinister Six, to causing the death of George Stacy, to his vicious (and nearly fatal) assault on Black Cat, Doctor Octopus has a long legacy in Spider-Man stories, which Peter Parker would like to forget. Though how can he forget the man who very nearly married his Aunt May?!

Whether his plans involve his brilliant knowledge of science or his desire to become a gang leader, "Doc Ock" has proven to be remarkably versatile in his talents, which has been bad news for Spider-Man over and over again. Like many great Spider-Man characters, there's tragedy to this villain too, as we, and Peter Parker, sometimes get a glimpse at the good intentioned man he once was, only for his dark side to take over once more.