Spider-Man’s rogues gallery is a veritable who's-who of monsters and misanthropes. Over the course of his decades-long career, Peter Parker has faced some of the most unhinged homicidal menaces New York City (and the world at large) has to offer. It’s not surprising, then, that some of Spider-Man’s villains have taken things entirely too far in their efforts to add more chaos to this cruel and indifferent world.
The enemies Spider-Man has fought have done some really messed up things to him that mark them as undeniably evil, but even then there’s a limit. There have been times over Spidey’s career where the reader has been forced to witness acts that can only be called demented or holy-balls-can-you-believe-that-guy-just-stole-Peter-Parker's-body and became the Superior Spider-Man?
While other heroes have it hard, the worst things that Spider-Man villains have ever done would make Wolverine run back to Canada.
Norman Osborn Seduces Spider-Man's Girlfriend, Gets Her Pregnant
In Amazing Spider-Man #509-514, a handwritten note sends Peter Parker down one of the darkest roads he has ever gone down. Parker discovers that not only did Norman Osborn kill Gwen Stacy, he also seduced and impregnated her beforehand (and she was pretty into it). Ugh.
Their children were born overseas in secret. Norman Osborn saw to their support, made sure they were educated and trained, and told them that Peter Parker was their father. Oh, also due to their Gobliny heritage, they aged super quickly. Because comics. The twins were told that Parker had abandoned them, killed their mother, and left them to die. Finally, Norman Osborn sent the children to destroy Peter Parker and all of his loved ones. So, the upshot is that Peter had to fight the children of his one true love and his greatest enemy, all the while dealing with the fact that Gwen Stacy cheated on him. It was a... rough time for the wall-crawler.
NYPD Captain and popular Spider-Man ally Jean DeWolff is dead, shot at close range with a double-barreled shotgun in her own apartment. It's a cheery way to start a story. Anyway, Spider-Man, Daredevil, and the entirety of the NYPD go on the hunt for her killer. While they search, the Sin-Eater continues his rampage across the city, eliminating anyone he deems guilty of sin.
Perhaps the most brutal of the Sin-Eater’s acts is the murder of Reverend Bernard Finn, a religious figure known for speaking in support of prison reform. Sin-Eater enters Rev. Finn’s confessional, and talks to the reverend about his self-doubt and flagging resolve.
Oblivious, Reverend Finn encourages him to remain true to his convictions, and to himself. In hindsight, this was probably a bad move. Sin-Eater thanks the Reverend for telling him what he needed to hear, then shoots him point blank with a shotgun, blasting him right out of the confessional in Spectacular Spider-Man #108.
Peter Parker is dying. A radioactivity-based infection is eating him from the inside, and despite the thousands of times Spider-Man has risked his life, this looks like his final battle. Reed Richards, Bruce Banner, T’Challa, and even Doctor Strange are all unable to save his irradiated life.
When Peter Parker is at his weakest, the villain Morlun attacks Spider-Man. The web-slinger is unable to mount a defense that even remotely slows his vampiric opponent's onslaught. Peter puts everything he has left into a vicious flurry of blows, and it appears that he's beaten Morlun into submission. Then Morlun goes ahead and rips out Peter’s left eye, devouring it in front of him before beating Spidey close to death in Amazing Spider-Man #526.
The Green Goblin Brutally Breaks Spider-Man's Spirit
Norman Osborn, AKA Green Goblin, isn't exactly what you'd call "well-adjusted." Or, you know, "merciful." So when Osborn kidnaps Spider-Man and tortures him (both psychologically and physically) with the intention of making him his heir, it's both horrifying and totally in character. Classic father-and-son stuff.
Eventually, Peter musters the strength to fight back and reject Norman Osborn’s twisted gift of darkness. He beats the crap out of the Green Goblin, but it doesn’t matter. Osborn knows that even though Spider-Man is stronger and smarter than he is, the Goblin has broken him. Osborn’s work is done, and in Spectacular Spider-Man #25 he leaves a weeping, unmasked Spider-Man behind him. For a while after that, Spider-Man is kind of a huge bummer to hang out with.
Doctor Kafka of Ravencroft Sanitarium spent a lot of time and effort trying to help the nightmarish killing machine Cletus Kasady, AKA Carnage. Unable to help him, Kafka calls in Matthew Kurtz from the Pentagon for assistance in rehabilitating the murderous psychopath.
Kurtz uses a sonic gun to control the alien symbiote in Kasady’s blood, also utilizing massive doses of psychotropic drugs to control Kasady himself. Kurtz peels back the layers of Kasady’s mind, cutting to the heart of Carnage’s psychopathy: it’s not just that Kasady loves to kill, he considers himself an artist.
When the drugs unexpectedly wear off early, Kasady attacks Matthew Kurtz with unearthly speed. Carnage drives a corkscrew spike into Kurtz’s mind and pumps his own twisted view of life and existence directly into Matthew Kurtz’s mind. The visions of unrelenting violence change Kurtz for the rest of his very short life as Carnage watches, contented and amused.
Green Goblin loves messing with Peter Parker. It's unstoppable, like the tides or new seasons of The Bachelor. As is often the case, Osborn wants Parker to join him as heir to the Osborn Empire. Barring that, he wants Parker to kill him or die knowing that Osborn will then kill everyone Parker has ever loved. Osborn doesn't really do grey areas.
To motivate the web-slinger, the Green Goblin forces a full bottle of whiskey down the throat of recovering alcoholic Flash Thompson, and then puts him behind the wheel of a speeding truck. A real classy move. The truck is pointed directly at Peter Parker’s unoccupied public school classroom (he's a teacher in this story), and the ensuing crash leaves Thompson with permanent brain damage in Peter Parker, Spider-Man #45.
The really messed up part? This was all tangential to the Goblin's main plan. He just wanted to make Spider-Man mad, and he ruined a man's life to do so.
