Whilst I do not mean it sincerely, I believe a good case could be made for the Jackal being in the top five. He put Spidey through as much misery as Marvel put Spider-Man fans through in the mid to late 90's, that is a bit of a feat. Whilst he was being partially manipulated by Osbourn, he still had his own special way off pissing Pete off what with Pete not knowing if he was a clone or not. That was originally Jackals idea and, thought it may have gone on longer, and twisted and turned more, and have been helped along by others, than any of us, characters or readers, wanted/needed it's still a rather nefarious scheme. He also created Kaine and, I am not ashamed to admit this, I love him: From veiny and spiky to bearded and rain mac'd, even to Scarlet and, err, in Huston. Jackal surely gets some kudos for that, right?
I find myself agreeing with Osborn being Pete's biggest nemesis and Ock being Spideys. I mostly feel that in a Spidey and Goblin match, Spidey has the advantage, but in Pete and Norman Pete is definitely the underdog. To me, Ock somehow feels more physically menacing, more so when he develops a 'personal forcefield', and seriously has some diabolical schemes to him, what with being Master Planner and Ends of the Earth right now. Heck, even close to dying the guy is giving not just Spidey but the whole world a serious beatdown, it's just a shame he didn't get married to/stayed married to (I forget which) May, then he could have challenged Norman on the Pete front too. Finally, without Ock, there would have been no Luke 'Calamari' Carlyle, who is definitely on of my favourite exceptionally minor Spidey villains. All of this is not bad for a guy who's, at least, ten times simpler than the bright spark (he he) electrician who decided to fix power-lines during a thunderstorm.
Still, I'd plump for Shocker. He was my favourite as 6 year old and, believe me, that guy had some pretty good ideas.
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