2. ACTION COMICS #583 (1986)

Alan Moore’s milestone Superman story, Whatever Happened to the Man of Tomorrow?, concluded in this issue and featured a cover by iconic artist Curt Swan. This image of a remorseful Man of Steel leaving his friends symbolized the end of a more innocent time in comics.

Moore’s story gave closure to the more light-hearted Superman era of the Silver Age before the character was modernized by John Byrne after Crisis on Infinite Earths.