10. Brain Damage And Beatings - Marvel Knights: Spider-Man Vol #1
The Marvel Knights series of Spider-Man stories have stood out over the years amongst others for being designed specifically with grittier, more mature approaches in mind. Because of this, the stakes are raised higher than ever before, and the artwork for each of Spidey's fights contain noticeably more blood, saliva and evidence of the beatings going down.
The premise in this series starts off fairly straightforward, with Aunt May being captured and Spider-Man being tasked with having to navigate through all of his most sinister foes with enough time left to save her.
The first issue sees Spidey come up against Norman Osborn's Green Goblin, and it's a fight that does an awesome job in laying down the new dark tone the series wants to run with. Spider-Man is a hero known for his wisecracks and jokes during a showdown, but this fight stands out for featuring the wall-crawler dishing out plenty of goads and jeers towards his foe in a manner that is honestly a little unsettling.
Seeing someone so morally uncorruptable as Spidey seemingly revelling in inflicting pain and having the upper hand in a fight makes for one dark departure for the franchise.