As writer Peter David’s first successful pitch to Marvel, The Death Of Jean DeWolff explored the moral relativism of superheroes and how each of these masked do-gooders go about their respective business in their own ways without any predetermined rules.

After Spider-Man’s ally within the NYPD, Capt. Jean DeWolff, is murdered in cold blood by the Sin Eater, Spidey loses it and goes to hunt down the assailant. Along the way, Daredevil aids the Wall Crawler while also trying to convince him that extreme violence won’t solve anything. This is the first storyline to show an enraged Spider-Man incapable of controlling his own emotions, and it’s easily one of the most frightening portrayals of the character yet.

Peter David presented both sides of the argument fully, and what’s even better is that every reader would have a different opinion on how Spider-Man should take justice on the Sin Eater. Some would want the killer dead; others, meanwhile would want Spidey to go by the books. Either way, David colors the world of superheroes in shades of grey rather than simple black and white.