10 Darkest Animated Spider-Man Moments
4. Harry's Declining Mind - Spider-Man: The Animated Series
The 90s Spider-Man animated series had a much more traditional interpretation of the Green Goblin saga than later interpretations for obvious reasons. This included a traditional fall for Harry Osborn, though the 90s show lets us into his head way more than the comics did.
While not the most complex fall in animation history, it's still pretty haunting to see Harry's mental state just flat out collapse. To the point where he's haunted by the specter of his father in the Green Goblin mask, goading him into continuing his work.
It doesn't even take that much to get Harry to do it, seeing as how the dude's been cookoo for coco puffs for a while at this point. But knowing he's that far gone, when we've spent entire seasons with him and peter is nothing short of dark as hell.