SUPERMAN, Vol. 1, No. 423 + ACTION COMICS, Vol. 1, No. 583: "Whatever Happened to the Man of Tomorrow?" (Moore / Swan; DC, 1986)
Filing yet another under the "no I can't believe I didn't read this until now either" header because, not only is "Whatever Happened to the Man of Tomorrow" now my favorite Superman story, but it's one of my favorite comics stories of all time, my ONCE UPON A TIME IN THE WEST of comics.
In fashion not dissimilar to Leone's masterful deconstruction and exploration of the mythological Western, the pairing of Moore's words with Curt Swan's immortal and character-defining pencils is magic: a deconstruction of the hallowed and iconic by a mind matched by few wrapped in a rousing action story with deep emotional stakes; a distillation of, at that point, nearly 50 years of monthly storytelling that not only showed why Superman has endured, but why he must: it's the first work anyone tasked with carrying on that legacy – be it in comics or in film or in any other media – should read; I can only hope that Gunn uses this as a guide – fortunately, from what he's said of what's coming in LEGACY, it sounds like he has. Certainly nailed the casting so far.
Other than Morrison and Quitely's ALL-STAR SUPERMAN (now my second-favorite Superman story and apparently one of Gunn's guiding texts), I can't think of another take that so deeply captures every facet of the character – the hope, the action, the sacrifice, the tragedy – in such a powerful, poignant, and emotionally satisfying way. Essential.