10 Villains That Tortured Spider-Man The Most

Split image of J. Jonah Jameson, the Green Goblin and Venom from Spider-Man
Source: Spider-Man, Marvel Comics

It’s a well-known fact that a hero can usually be defined by the notoriety of his or her villainous enemies. It’s hard to think of any hero that has been put through the ringer more and suffered more torturous tragedy than Spider-Man.

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It might be because of the wall crawler’s relentless idealism, or maybe because he attracts tragedy just because of his character. But regardless of the circumstances, he’s been through a lot of heartache and drama in his life, most of it caused by villains he’s encountered along the way.

10) Ana Kravinoff

Source: The Amazing Spider-Man, Marvel

Although she might not be considered a powerhouse villain of Spider-Man’s, it’s hard to overlook exactly what Kraven’s daughter put him through. A lot of people want to take revenge on Spider-Man, but her gauntlet was relentless.

She manipulated and arranged for every one of Spidey’s classic villains to challenge him and wear him down. By the end of the campaign, Spidey was so exhausted that Ana, who was essentially a kid at the time, was able to enact such a master plan.

9) The Kingpin


Source: The Kingpin, Marvel

Much like Daredevil, Spider-Man has always had a particular grudge against the Kingpin. Of course, he’s always faced off against various supervillain crime bosses like Tombstone and Hammerhead, but there’s something about Kingpin, a model of corruption, that goes against the very ideals Spidey is fighting to uphold.

Wilson Fisk hasn’t really traumatized Spider-Man on a personal level, but he’s that one nagging force in New York City’s underworld that will always be there. Kingpin will never be gone for good, and because of that, he’s the one foe Spider-Man will always have to contend with.

8) Venom

Source: The Amazing Spider-Man, Marvel

Given that he’s now pretty much solidified as an anti-hero, it’s hard imagining Venom as a villain that tortured Spider-Man, but when he first emerged on the scene, Venom had a huge grudge against the wall crawler.

The black suit symbiote had taken a toll on Spider-Man all by itself. When it bonded with Eddie Brock, a man who had just as much animosity for the hero, the amalgamated Venom went for the jugular by kidnapping Mary Jane. They would eventually reconcile as bigger threats emerged, but the confrontation traumatized Spidey so much that he gave up the black suit because of it.

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7) The Jackal

Source: The Amazing Spider-Man, Marvel

The Clone Saga is very often ridiculed by fans, and rightly so. It was goofy at its worst, and short-sighted at best, but that didn’t mean it didn’t take its toll on Spider-Man from beginning to end, and it all started with the Jackal. From clones of himself, to his dead girlfriend Gwen Stacy, Peter Parker had a lot to deal with thanks to Miles Warren.

Later on, it became even more troublesome when Ben Reilly and Kane emerged onto the scene, as well as a twisted version of Miles Warren named Carrion. Regardless of the legacy of the Clone Saga, the Jackal certainly did a number on Spider-Man because of it. That doesn’t even take into account the fact that he first brought us the Punisher.

6) Doctor Octopus

Source: The Amazing Spider-Man, Marvel

From the very beginning, Dr. Octopus has always been a menacing threat to Spider-Man, as evidenced by the fact that he formed the Sinister Six to take him down for good.

There are tons of examples of how Doc Ock did a number on Spidey, but the most recent example of when he became the Superior Spider-Man might be the worst. He didn’t just manage to kill Peter Parker – he also took over his life and wreaked havoc on it for a fairly long time. It was such an ordeal that Peter had a lot to make up for when he eventually reclaimed his body.

5) Kraven The Hunter

Source: The Amazing Spider-Man, Marvel

Very few villains have single-handedly beaten Spider-Man the way Kraven did. It was such a monumental victory that “Kraven’s Last Hunt” has become a landmark Spider-Man story.

Of course, no villain stays dead forever. Kraven and his saga have continued on past his death. Nick Spencer’s run on Amazing Spider-Man has garnered mixed reviews, but a highlight was when Kraven started a hunt involving Spider-Man and other animal-themed villains in Central Park.

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4) Harry Osborn

Source: The Amazing Spider-Man, Marvel

Harry Osborn is a tragic figure himself, but he has done a fairly decent job of terrorizing Spider-Man in spite of that. Besides the fact he became the second Green Goblin, he also arranged for Spider-Man’s parents to return as clones to terrorize him.

More recently, Harry also returned as the demonic Kindred to emotionally torture Peter again. As a villain, Kindred had a mixed reception, but there’s no denying that he certainly knew how to torture Peter from start to finish by bringing his dead loved ones back for a bizarre dinner party.

3) Norman Osborn

Green Goblin

Source: The Amazing Spider-Man, Marvel

It’s not surprising that Sam Raimi chose Green Goblin to be the villain in the first Spider-Man movie. Norman Osborn is perhaps Spider-Man’s one true nemesis, and has tortured him more than any other supervillain.

A list could be made of all of the devilish deeds the Green Goblin has done to Spider-Man, but it’s hard to think of one that tops the death of Gwen Stacy. Despite having a great relationship with MJ, Peter’s first true love will always be Gwen, and he will never forgive Norman for taking her away from him.

2) J. Jonah Jameson

Jonah Jameson and Spider-Man have a very long and interesting history. It’s probably more complicated than any other relationship in the Marvel Universe. Since he has become a champion for Spider-Man, it’s hard to remember a time when Jonah was a Spidey critic.

When looked at over the course of Spider-Man’s career, Jonah caused a lot of grief and headaches for the wall crawler. This includes being critical of him in the Daily Bugle, to creating the Spider Slayers, and even having a hand in Mac Gargan becoming the Scorpion. It’s a brutal relationship that was really fleshed out in Spider-Man: Life Story.

1) The Burglar

Source: Amazing Fantasy #15: Spider-Man!, Marvel

When it comes to Spider-Man and the emotional torture he’s had to endure, one person stands at the top of that list. Fans of Spidey have to remember that he got his powers as a high schooler who thought they were the coolest thing in the world. To have his entire world turned upside down by the death of his father figure must have been heart-wrenching.

The burglar that ended up taking Uncle Ben’s life might not have been a supervillain, but he certainly changed the entire course of Spider-Man’s life. That one disastrous decision for Spider-Man to let him go sent the youngster on a path of guilt that would drive his heroics his entire life. That kind of deep characterization is hard to top.

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