(Warning - major plot SPOILERS for past Spider-Man comic book storylines lie below. Proceed with whatever level of caution your natural SPOILER-aversion suggests...)
Over the years, Spider-Man's had about as many villains come after him as any other superhero known to man - with some of them proving as lethal as they come. Whether he's having his romantic life ruined by The Kingpin, being buried alive by Kraven the Hunter, or even being convinced that he's a clone by The Jackal, there've been few moments in Peter Parker's life where he wasn't being completely screwed over by one foe or another. Heck, Doctor Octopus even spent most of the past few years forcibly occupying Peter's body...
All of them, though, pale in comparison to Peter Parker's most dastardly and consistently despicable foe. Y'see, when it comes right down to it...
Nobody's Worse Than the Green Goblin
That's right - over the years, Norman 'Green Goblin' Osborn has proven beyond a shadow of a doubt that, when it comes to Spider-Man, no-one can top his enthusiasm for causing endless misery.
Here, then, are five of his most fundamentally unpleasant moments...
5) Norman Faked Aunt May's Death
Yup, that's right - back in Amazing Spider-Man #441, it turned out that Norman had (40 issues earlier) faked the death of Peter's beloved Aunt May...by replacing her with an actress.
Norman's big reveal - that Aunt May was, in fact, still alive - wasn't all he had cooked up for Spidey, however. As it turned out, he'd hooked up the real May's brain to a 'DNA bomb' which would kill thousands if disconnected. Which Peter of course found a way to fix, but even so...
Dick move, Norm...
Though, arguably not as much of one as that time...
4) Norman Convinced Peter That He Was a Clone
Remember that whole Clone Saga dealio back in the 90's? Y'know, the one most fans hate with the burning passion of a thousand highly romantic suns?
Well, as it turns out, Norman Osborn was behind the whole thing. He spent years persuading Peter that he was in fact nothing more than a clone, ultimately achieving what punching and goblin gliders never could: Peter Parker stepping down as Spider-Man. Which, inevitably, didn't last, but it was still horrifyingly traumatic for Peter (and his clone, Ben Reilly, of course - who Norman brutally murdered)...
3) Norman Murdered Gwen Stacy
One of the most iconic moments in comic book history, the death of Gwen Stacy (after the Green Goblin dropped her from a bridge, snapping her neck) arguably defined the course of Spider-Man's adult life more than any other.
It was also, though, the brutal murder of a young, innocent woman, just to spite a costumed enemy. Which is pretty fundamentally awful.
Except perhaps not quite as bad as what happened a little while before it. Y'see:
2) Norman 'Seduced' Gwen Stacy
That's right - not long before he killed her, Norman Osborn and Gwen Stacy totally had sex. Which resulted in her getting pregnant. And having twins. Who Norman then turned into Spider-Man-battling killing machines.
Which is all pretty fundamentally terrible (especially seeing as it implies Norman actually killed Gwen to get her out of the way after giving birth), but especially so since it's entirely possible that the whole thing was less than consensual.
The only thing that can beat that out to the number one spot, then?
1) Norman Killed Peter's Daughter
Yup, that's right - just as the Clone Saga was finishing up, Norman hired a woman - Alison Mongraine - to poison the pregnant Mary Jane, causing her to have a miscarriage.
Or - just possibly - he actually kidnapped the baby...and then seemingly killed the child himself:
Either way, it's no wonder Norman Osborn is one of the most hated figures in comic book-dom. Murder, manipulation, possible sexual-assault and kidnapping are horrifying, and all - but child-murder? That's a particular low...