Out of all the heroes who are residents of the Marvel library, Spider-Man might have the best rogues gallery. He might even have the best set of villains in all comic book universes. The two most famous, and possibly most dangerous,s of his villains are The Green Goblin and Doctor Octopus.
Norman Osborne and Otto Octavius were both men trying to make the world better, but they failed miserably and ended up creating pain and suffering. They have both tormented Peter relentlessly over the years, each villain trying desperately to kill Spider-Man.
10 Green Goblin: He Killed Gwen Stacey
One of the absolute worst things that the Green Goblin ever did was the murder of Gwen Stacey. This immediately makes him one of the Wallcrawler's cruelest villains. The death of Gwen was a defining moment in Spider-Man's crime fighting career. To this day. this one of the worst losses Spider-Man ever suffered and it continues to haunt him to this day. This murder set the Goblin apart, not only from the rest of the Spider-Man mythos but from the catalog of supervillains in general.
9 Doc Ock: Stole Peter's Life
Doctor Octopus is arrogant and cunning and he uses his intellect to commit his crimes. When his body was crumbling from sickness, he devised a way to save himself. He decided to take over Peter Parker's body and live out his life in a strong body and his genius intact. He then became the Superior Spider-Man, stealing every aspect of Peter's life. And while he may have done some good while in the role, he still almost killed Peter's consciousness. It was a genius move that could only be imagined and executed by a top-tier villain.
8 Green Goblin: Framed Peter For Murder
When physical pain can't hurt Spider-Man, Green Goblin resorts to emotional and mental torture. The Green Goblin isn't just a man on a glider, Norman Osborne is also a rich and powerful industrialist. He used this power to buy the Daily Bugle and obtain pictures of Spider-Man beating him up. He also used his resources to frame Spider-Man as a murderer. This ruined Webhead's image and turned the public against the web-slinger once again. It was a clever and extremely manipulative plan, striking indirectly at his enemy.
7 Doc Ock: Tried To Marry Aunt May
Doc Ock was a cruel man in his early days, and he manipulated Peter Parker's Aunt May into marrying him, and it wasn't even to get back at Spider-Man! Of course, this drove Peter insane, seeing his Aunt fall for one of his worst villains, but Peter's secret identity got in the way of his credibility. In a bizarre twist, Otto was marrying Aunt May so he could gain access to a Canadian nuclear facility that Aunt May had inherited from a relative. It demonstrates the insane lengths that Doc Ock will go to in order to wreak havoc and destruction.
6 Green Goblin: Transforming Carlie Cooper Into A Goblin
Carlie Cooper was Peter Parker's one-time girlfriend and worked for the NYPD. Green Goblin once again set out to destroy the life of someone Peter loved in order to deeply hurt the Spider-Man. Green Goblin was torturing Carlie for information on Spider-Man, since she had just discovered the truth about the Superior Spider-Man, but she refused to help Norman.
Out of anger, Osborne sprayed her with his goblin formula to make her just like them. It was cruel and a senseless act of rage that was only meant to harm Carlie because she knew Spider-Man's identity.
5 Doc Ock: He Is Able To Gain Peter's Sympathy
More than most other Spider-Man villains, Doc Ock is able to gain Peter's sympathy and respect. The Green Goblin immediately enrages Peter and makes Spider-Man hate him, but Otto is different. Peter still believes that there is good inside of Doctor Octavius. Doc Ock uses this against Peter whenever he can, luring him in with empathy then executing his master plan. Doc Ock knows how to manipulate Spider-Man's belief in humanity better than any other villain.
4 Green Goblin: Merges With Carnage To Become Red Goblin
This was Norman Osborne's ultimate plan, where he meant to kill Spider-Man or die trying. He merged himself with the Carnage symbiote and became the Red Goblin. He gained new powers and lost all his old weaknesses. He struck out at his own family, at Spider-Man, and at anyone who was in his way. His viciousness and cruelty as the Red Goblin speak to Osborne's capacity for evil and his willingness to sacrifice innocent lives and loved ones. The Red Goblin was what Norman always wanted the Green Goblin to be, true evil unleashed on the world.
3 Doc Ock: Killed Captain Stacey
Doc Ock and Spider-Man met to fight again, and once again innocent lives were put in harm's way. Doc Ock could have tried to face Spider-Man away from the public, but he doesn't care about the collateral damage he causes. In this fight, NYPD Captain George Stacey happened to get in Octavius's way. While saving a child, Stacey was crushed by falling debris. This was a big loss for Peter and Doc Ock bore much of the responsibility for the situation that killed Gwen Stacey's father.
2 Green Goblin: Had Children With Gwen Stacey
This is one of the most controversial Spider-Man storylines and it may be Green Goblin's worst act. It was revealed that Norman and Gwen had two children together. This knowledge broke Peter and emotionally crippled him. Norman relished the emotional pain he'd inflicted, but a recent retcon revealed that these events were actually an intricate deception. Green Goblin is a master at finding an adversary's weakness and exploiting it to cause maximum pain.
1 Doc Ock: Formed The Sinister Six
What elevates Doc Ock beyond most of Spider-Man's villains is that he had the foresight to form the Sinister Six. This group of villains caused massive amounts of damage to Spider-Man over the years and continue to do more with every evolution of the team. Doc Ock brought the original team together, he was the first to realize that they were more effective together and that they could ruin Spider-Man if they worked as a team.