Easily one of the most important stories in comic book history, The Night Gwen Stacy Died marked the end of the more positive Silver Age of comics and ushered in the Bronze Age, a time when comics began to show their teeth a little.

Gwen Stacy was Peter Parker’s first love, and all of the writers and editors at the company just assumed that they would get married eventually. However, the idea of a married Spider-Man would drastically limit the character's story possibilities, so writer Gerry Conway, artist John Romita, and editor Roy Thomas decided to kill Gwen off in order to prevent Spidey from getting hitched.

Gwen died during a battle between Spider-Man and Green Goblin; she was thrown off the Brooklyn Bridge (or the GWB, as some fans would have you believe.) Even though Spider-Man shot a web and saved her before she hit the water, the shock of the event, combined with the sudden stop from the web, caused her death.

While characters like Batman and Daredevil receive all of the press for being “dark” and “gritty,” this story started the whole movement of superhero comics getting violent. The Night Gwen Stacy Died was revolutionary in that regard, and, ever since its release, no supporting character has been off limits from the Grim Reaper’s grim embrace.