As one of Marvel Comics' first and most prolific superheroes, Spider-Man/Peter Parker has fought his fair share of super-villains over his many adventures on comic and celluloid alike. Indeed, Spider-Man's vast and distinctive Rogues Gallery is often described as one of the greatest in the annals of superhero comics. However, two adversaries stand above the rest: The Green Goblin/Norman Osborn and Doctor Octopus/Otto Octavius.

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Only one can claim the exclusive title of "arch-enemy;" Spider-Man co-creator Stan Lee voiced the opinion "The Green Goblin is Peter Parker's greatest enemy, while Doctor Octopus is Spider-Man's greatest enemy." Let's take a look at what Osborn and Octavius bring to the table to see if Lee's statement stacks up.

10 Green Goblin: First Villain to Discover Peter's Secret Identity

Peter Parker's most closely-guarded secret is his web-slinging alter-ego; as such, it's ironically fitting that the first of his nemeses to discover it would be one whose own secret identity had been a mystery for so long. In The Amazing Spider-Man #39, the Goblin surreptitiously observes Spider-Man, witnesses him unmasking, then follows him home. Caught off guard, Peter is abducted by the Goblin and brought to the villain's factory hideout, where Osborn unmasks himself to Peter and the two engage in a climactic struggle. Of course, the writers couldn't have one of Spider-Man's greatest enemies knowing his identity and roaming free, resulting in Norman developing a bout of amnesia after a hit on the head. While other villains have unmasked Spider-Man since, The Green Goblin was the first to do so, and that accomplishment alone pushes him to the heights of the rogues gallery.

9 Doc Ock: First Villain To Defeat Spider-Man

The first impression is often the strongest, and it was Doctor Octopus who first appeared in the pages of The Amazing Spider-Man. Debuting in the series' 3rd issue, Doc Ock was preceded in appearance only by The Chameleon and The Vulture, and unlike them, he proved a physical challenge for the web-slinger. Advertised as "The only enemy to ever defeat Spider-Man," Octavius received his mechanical arms in a science experiment gone wrong that mirrored Spider-Man's own origin.

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True to the issue's proclamations, the mechanical appendages proved too much for Spider-Man and Doc Ock prevailed in their first encounter. While Spider-Man later triumphed through some clever thinking, the David vs Goliath dynamic established between Spider-Man and Doctor Octopus would define their relationship going forward.

8 Green Goblin: A Billionaire Villain For A Working Class Hero

What sets the Friendly Neighborhood Spider-Man apart from most of his superhero brethren is his down-to-earth struggles; in addition to crime capers and world-ending-threats, Peter faces challenges such as maintaining a job, keeping up with schoolwork, and paying the rent. He's a superhero who embodies the struggles of working people, and as such, it's only fitting that his premier villain would be a billionaire CEO. Head of chemical company OSCORP, Osborn's vast financial resources enable him to fund his criminal activities and various devices he employs as the Goblin, compared to the often cash-strapped Peter.

7 Doc Ock: A Scientist Villain for a Science-Loving Hero

A dedicated student, Peter Parker had a strong passion for science even before it granted him superpowers; it was Peter himself who designed the web-shooters that have proved so useful to his superhero self. As a textbook "mad scientist," Doctor Octopus provides a dark mirror to Peter's love of science; he built his own harness much like Peter built his web-shooters, both their origins like in science-gone-wrong, and the similarly bookish Octavius' criminal escapades show what Spider-Man could have become if not for Peter's moral compass.

6 The Green Goblin: A Surrogate Father

In 2000's Revenge Of The Green Goblin, Norman realizes that it's Peter, not his own underachieving son Harry, who embodies many of the same traits in himself that he values - intelligence, determination, self-made - and so resolves to coax Peter into becoming his heir.

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This idea was so brilliant - a young man lacking a father figure can only find one in his greatest enemy, a man who's own son disappointed him so much that he's sought out a replacement - that subsequent Spider-Man media, such as Sam Raimi's film trilogy, Brian Michael Bendis' superlative Ultimate Spider-Man run, and the unfortunately abbreviated Spectacular Spider-Man animated series incorporated this into Peter and Norman's dynamic from the beginning. It's a great example of revisions strengthening characters rather than detracting from them and adds a complexity to the rivalry between the Goblin and Spider-Man that none of the former's villains can hope to match.

5 Doc Ock: A More Consistent Menace

Since the character's first appearance, Doctor Octopus has been Spider-Man's most frequent adversary. Octavius was the first of Spider-Man's rogues' gallery to make a second appearance after his debut, in The Amazing Spider-Man #11, and his appearances haven't slowed up since. Furthermore, while death is rarely a permanent affair in comics, but for over twenty years between 1973 and 1996, Norman Osborn was considered well and truly dead. As such, there is a gap between his encounters with Spider-Man, a gap that Doc Ock more than filled. Continuing to appear on a consistent basis throughout Osborn's absence, some of Octopus' notable misdeeds during this period include putting Spider-Man's then-partner (in the professional and romantic sense) Black Cat in the hospital and attempting to destroy New York with a nuclear reactor.

4 Green Goblin: The Goblin Legacy

While Norman Osborn may have the first and most famous man behind the Green Goblin's mask, he's far from the only one who's worn the costume and ridden the glider at this point. The Green Goblin has inspired a cadre of copycats, all of whom have been a thorn in Spider-Man's side. Some of the most prominent ones include Osborn's son Harry, who first took up the persona in The Amazing Spider-Man #136 and has done so intermittently since, and The Hobgoblin, aka Roderick Kingsley, a fashion mogul and aspiring crime boss who discovered one of Osborn's abandoned hideouts and took the contents from himself.

3 Doc Ock: Founder Of The Sinister Six

Few things are worse for a superhero than when multiple super-villains they've faced before team-up to fight them simultaneously; for Spider-Man, these recurring villain team-ups adopt the name of "The Sinister Six." The existence of the Sinister Six can be traced back to Doctor Octopus; it was him who organized the first iteration of the team in The Amazing Spider-Man Annual #1 and the second in the six-part Return Of The Sinister Six (The Amazing Spider-Man #334–339). There have been many versions of the Six since, but they can all be ultimately traced back to Ock's original team.

2 The Green Goblin: Killed Peter's First Love

Spider-Man vowing revenge after the death of Gwen Stacy

No list mentioning the Green Goblin's crimes against Spider-Man could elide this; in possibly the most brutal blow a villain has ever dealt a hero in comics history, the Green Goblin ended the life of Gwen Stacy, Peter Parker's first true love, when he threw her off the George Washington Bridge in The Amazing Spider-Man #121.

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The shadow of this event has loomed large over all Spider-Man stories told since, and even as Peter's found new relationships since, his failure to save Gwen and the memory of his dearly-missed beloved forever haunts him. To paraphrase another great villain: by killing Gwen, Osborn did far worse than kill Peter. He hurt him.

1 Doc Ock: Stole Spider-Man's Life

Doc Ock's Coup de grâce occurred in the "Dying Wish" storyline of The Amazing Spider-Man, where he swapped his consciousness with Peter's, allowing him to take control of Spider-Man's body while Peter was left to die in Octavius' ailing one. Spinning off into The Superior Spider-Man, which featured Octavius assuming the role of Spider-Man in an attempt to prove himself a better hero than his greatest enemy ever was. While the status quo eventually reasserted itself, no other adversary of Spider-Man's has ever mounted so personal an attack on the hero; that it succeeded is just the rancid cherry-on-top.

NEXT: Spider-Man: 5 Reasons Doc Ock Is Better As A Hero (& 5 Why He's A Better Villain)