Spider-Man has had plenty of enemies over the years, but none how been as psychologically devious as Norman Osborn. As the Green Goblin, Osborn has been responsible for some of the most heinous acts ever seen in the history of Marvel, hurting the ones Peter Parker loves the most and becoming obsessed with the downfall of the webslinger.
Whether the pain has been of a mental or physical nature, the Green Goblin has pushed the limits of how far someone can go to bring down their enemy. On that note, we've decided to look at the 10 most evil things Norman Osborn has done to Spider-Man.
10 Faking Aunt May's Death
In Amazing Spider-Man #400, we witnessed one of the most poignant and emotional stories in comics: Aunt May came out of her coma just to spend a little more time with Peter Parker before she passed away, acknowledging she always knew her nephew was Spider-Man. As she took her final breath, she told him how she couldn't have been more proud.
However, after Parker moves past the grief of losing May, Osborn drops the bombshell that she's still alive, and that the one that 'died' was an actress he hired. Not only that, but when he finally finds her, she's been implanted with a bomb that could wipe out thousands of innocent people. What a jerk.
9 Ben Reilly's Death
For years, Ben Reilly and Spider-Man would battle with the notion that one of them was real, and the other was a clone. In that time, they both grew close, with Parker seeing Reilly as his brother. When Reilly becomes Spider-Man after Parker retires, Osborn seizes the opportunity to kill Parker once and for all.
When a fight breaks out between all three of them, Osborn sees an opening to end his nemesis' life, but in the process Reilly gets in the way and is impaled by the Goblin Glider. With his final breath, Reilly tells Parker to become Spider-Man once again. As Reilly turns to dust, Parker finally realises that he's not the clone at all, but the real deal.
8 Flash Thompson's Car Accident
In one of the most sickening storylines seen in Spider-Man comics, Peter Parker: Spider-Man #45 sees Norman Osborn meet up with Flash Thompson after attending one of his Alcoholics Anonymous meetings. Osborn takes advantage of Thompson's weakness and pours copious amounts of alcohol down his throat, shortly after lulling him into a false sense of security.
We then see Thompson behind the wheel of an Osborn Industries lorry, unable to steer as he's completely inebriated. The lorry crashes into the side of the school where Parker now teaches, and it's explained that he was six times over the legal limit. This gives Thompson brain damage, and solidifies the Green Goblin as a truly evil villain.
7 Spider-Man Is Framed For Murder
One thing Norman Osborn is known for is his intellect. He orchestrates one of his smartest plans yet by framing Spider-Man for murder. He purchases the Daily Bugle, and uses his wealth to put the wheels in motion on his latest plan to bring down his greatest enemy.
With a $5 million bounty on his head, Spider-Man must evade capture by the likes of the Punisher, Overdrive, and Arthur Stacy, and find a way to prove that he never killed the lowlife Joey-Z. Of course, Spider-Man manages to prove his innocence during the Identity Crisis story arc, but it's yet another fiendish scheme by Norman Osborn.
6 The Apparent Death Of Peter and Mary Jane's Baby
In yet another uncomfortable and frankly disturbing plot to mess with Spider-Man, Norman Osborn manages to steal away the supposedly stillborn baby of Peter Parker and Mary Jane. With Parker and Ben Reilly as Spider-Man fighting Gaunt and his army of robots, Mary Jane is having a painful labor. In harrowing fashion, the baby is announced dead.
With Mary Jane hysterically crying as her baby is wheeled away, it cuts to a pier with a mysterious figure - revealed to be Osborn - ready to transport the baby along with the mysterious nurse who helped deliver her, to Europe. It showed that there're no lengths he won't go to in bringing down Parker and everyone he loves. A truly disgusting act of revenge.
5 Burying Aunt May Alive
Surprise, surprise! Norman Osborn is back to his evil ways in The Last Stand storyline from Marvel Knights: Spider-Man. He manages to get Spider-Man to break him out of prison by using Aunt May's disappearance against him. When Osborn reveals that May only has 30 minutes of oxygen left before she dies, Parker frantically searches New York to find her.
You'd think that almost losing Mary Jane in the same way Gwen Stacy died would be the worst thing about this arc, but May's near death tops it. Thankfully, he manages to find her buried alive next to the grave of Uncle Ben. It's gruesome, shocking, but nothing out the ordinary as far as Osborn is concerned.
4 Carlie Cooper Becomes A Monster
Norman Osborn has demonstrated time and time again that he knows how to get under Spider-Man's skin by hurting the people he loves the most. Carlie Cooper was an NYPD officer who once dated Parker, and when she found out that Doctor Octopus was Spider-Man in the Superior Spider-Man comics, Osborn needed to know.
Menace - one of the Green Goblin's minions - manages to kidnap Cooper and bring her to the Goblin King. When she refused to divulge the information he craved, she was sprayed with the Goblin formula and turned into a hideous monster. She eventually returned to normal, but was never the same again.
3 Gwen Stacy And Norman Osborn Have Children Together
The most devastating thing about this storyline is the fact that it undoes all the fan's feelings towards Gwen Stacy. When she died it left the world in mourning, providing a genuinely heart-breaking end to Amazing Spider-Man #121. However, in Sins Past, we learn that whilst in Europe, Osborn and Stacy had children together, and due to their offspring being related to the Green Goblin, they had unique abilities similar to their father.
The twins - Gabriel and Sarah Stacy - confront Spider-Man and all is revealed. Mary Jane ends up telling Peter Parker she always knew, but promised she wouldn't say anything after Gwen Stacy swore her to secrecy. It's generally regarded as one of the worst Spider-Man storylines, and with this revelation, you can see why.
2 The Goblin Heir
In the Revenge of the Green Goblin story arc, Norman Osborn attempts to bring in Spider-Man as the heir to his Goblin legacy. Peter Parker receives a tube of toothpaste laced with hallucinogenics based on the Goblin formula, and also receives a CD featuring Uncle Ben's music, but it has subliminal messages built into the recordings.
What follows is the torture of Parker at the hands of the Green Goblin. Beaten and broken, Parker almost gives into the darkness, but thankfully manages to escape. Even though he breaks free, Osborn finds some solace in the fact that, for a second, Spider-Man almost gave in, and that one day he might fully embrace his evil side.
1 The Death Of Gwen Stacy
When Gwen Stacy died, it marked a turn in Marvel comics. Darker storylines started to creep in, providing more mature themes from then on. Whilst the Sins Past story arc has certainly changed many fan's opinions on Stacy's death, at the time it was one of the first big deaths in Marvel's history.
After being thrown from the top of the Brooklyn Bridge, Spider-Man attempted to rescue her by firing his webbing and seemingly saving her. He celebrates, thinking he's saved her life, but it's revealed that the speed at which she was falling and the sudden jolt of the webbing breaking her fall snapped her neck. The iconic image of Spider-Man holding her lifeless body still sends shivers down the spines of Spider-Man fans across the world.