The 20 greatest (and 10 worst) Spider-Man villains of all time

9th Worst Villain: Jason Macendale/Jack O’Lantern/Hobgoblin/Demogoblin

There was once a CIA operative named Jason Macendale, and he was a loser. The CIA fired him for being too aggressive, so he became a mercenary. And since costumed bad guys were all the rage, Macendale decided he needed a costume, too. He decided on a Halloween gimmick consisting of a flaming pumpkin a head, rode around a hover board, had an arsenal of spherical grenades, and called himself Jack O’Lantern.

But Macendale saw The Hobgoblin had a better Halloween gimmick, and decided to steal it from him. After figuring out the Hobgoblin’s identity as Daily Bugle reporter Ned Leeds, Macendale hired another mercenary called the Foreigner to have Leeds killed.

But even after becoming the new Hobgoblin, Macendale was still a loser because he lacked super powers. So when demons invaded New York, Macendale decided to make a deal with one them. This act bound his soul with a demon driven to punish “sinners,” and distorting his face in the bargain. Only later did this demon realize, “This mortal is too much of loser even for me,” and forcibly separated itself from Macendale. Unfortunately, having possessed him for so long, it became an even bigger loser dubbed The Demogoglin.

Powerless once again, Macendale drank one of Kraven the Hunter’s old potions, which made him strong enough to kill The Demogoblin. He even went as far as augmenting himself with cybernetic enhancements. Eventually, the authorities arrested Macendale, and while in prison awaiting trial, Roderick Kingsley–the real Hobgoblin–appeared. He essentially told Macendale, “I had enough of you ruining my reputation,” and blew him to smithereens. Thus Macendale, a loser in life, died a loser in the end.