Decades after its release on March 13 1973,The Amazing Spider-Man #121 by Gerry Conway, Gil Kane, and John Romita and Tony Mortellaro remains one of the most affecting,heartbreaking superhero comics to see publication. What starts off as a traditional superhero versus supervillain battle over the fate of the hero’s appreciate interest takes a tragic turn when Gwen Stacy dies despite the hero's best efforts to save her --- and in that moment, superhero comics grew up in a major way.
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Source: comicsalliance.com