Here are the top 5 and here's why for each one.
1- Green Goblin: Hands down his arch-nemesis. Has caused him more pain than anyone else. Killed Gwen Stacy, killed Ben Reilly, turned the entire city against him in Identity Crisis, cause Harry to use drugs and made him go crazy, made Flash Thompson, a recovering alcoholic, drink again and almost got him killed, buried Aunt May alive, tried to kill MJ several times, almost made Peter himself go crazy and inject the Goblin Serum, had an affair with Gwen and caused their children to go after him, just to name a few...
2- Doc Ock: Almost made the top spot. Before Goblin killed Gwen, Ock was Spidey's most dangerous foe. He gave Spidey his first real defeat, almost unmasked him in front of his friends, He caused the death of George Stacy (albeit accidentally), almost hooked up with Aunt May and tried to use a nuclear device on the city, held the whole world hostage in Ends of the Earth and led to the death of Silver Sable, Spider-Man always barely manages to beat his plots, and let's not forget the Superior Spider-Man saga.
3- Venom: The symbiote has been a thorn in Spidey's side for many years. When it bonded to him, it almost killed him had he not seperated himself from it, then it bonded with Eddie Brock and terrorized him for years, Spidey was physically no match for Venom, he kidnapped and tried to kill MJ many times, he kidnapped Peter's (fake) parents. Even after it seperated from Brock, it bonded to other hosts who also terrorized Peter.
4- Hobgoblin: Terrorized Peter for many years without him knowing his true identity. Caused the death of Ned Leeds which haunted Peter for many years, led a gang war that almost destroyed the city, gave him some of his vicious fights ever.
5- Kraven: Kraven makes this list simply because of Kraven's Last Hunt and Grim Hunt, besides those stories, Kraven was never a major villain. But in KLH, he did something most of his villains couldn't do, defeat him and prove his superiority.
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