#1: Gwen Stacy (Amazing Spider-Man #121)
After scraping the bottom of the dating barrel for years, Peter Parker had seemingly hit a home run when he started to date Gwen Stacy, who was way hotter than him. However, it wasn’t long before the Green Goblin used Gwen as a pawn in his unending crusade to torture Spider-Man. After kidnapping Gwen and leading Spider-Man to the Brooklyn Bridge (or George Washington Bridge, depending on who you ask) the Goblin threw her off the bridge. Spider-Man tried valiantly to save her but she died after he caught her in his a web. It’s still unclear whether the shock of the fall or the sudden force of Spider-Man’s webbing led to her death, but the fact remains that Gwen Stacy’s death in June 1973 is the most memorable in comics. Her death marked a turning point in comic book writing as after that no one was truly safe from a villain and even an innocent character could be killed.