In yet another example of a milestone issue number coinciding with a major character’s death, Spectacular Spider-Man #200 saw the Grim Reaper set his sights on Harry Osborn. Harry was the son of Norman Osborn, a.k.a. the Green Goblin, yet he was also Peter Parker’s best friend. But the cheese eventually slipped off Harry's cracker and he became the new, and somehow crazier, Green Goblin.

While this issues does include the requisite fighting and explosions, coupled with more whacky Green Goblin shenanigans, Spectacular Spider-Man #200 actually packs an emotional punch at the end when Harry saves Peter’s life from an explosion. But with Harry weakened by fever, no thanks  having the Goblin's formula in his blood, he soon collapses. In the ambulance, Spider-Man stays with his one-time friend and asks Harry why he helped him. Harry simply replies, “Because you’re my best friend.” The two hold hands until Harry dies on the way to the hospital.

It's one of the more impactful moments in the character’s history. Too bad Hollywood screwed the pooch when they tried to recreate this moment in 2007's abysmal Spider-Man 3.