[[caption-width-right:350:I knew something had upset him. He looked funny. He looked as if he'd been crying.]]

* The cover of Action Comics #583, with the sad expression on Supes face as he flies off - forever.
* The death of Krypto.
* The death of Bizarro.
--> Hm, everything, him go dark... Hello, Superman. Hello.
** This has got to be one of the saddest character deaths ever. Compounded by the fact that Bizarro clearly has no idea what is happening.
* Comicbook/{{Supergirl}} came from the future with the ''Comicbook/LegionOfSuperHeroes'', before [[ComicBook/CrisisOnInfiniteEarths her eventual death]].
--> '''Superman:''' You... you grew up beautiful, Kara!... Right now, Supergirl... [[HeroicSacrifice Supergirl is in the past.]]
** In the same encounter, the fact that the Legion are here to see their friend one last time.
--->'''Cosmic Boy''': Goodbye, Superman. We... we ''always'' miss you.
** Fridge Sadness: The reason the Legion brought Supergirl with them in the first place.
* ''Lois: "He never told me exactly what happened that night before the siege began, but as soon as I saw him the next morning, I knew something had upset him. He looked funny. He looked as if he'd been [[ManlyTears crying]]."''
* Lana Lang, after hearing from Superman's own lips (thanks to newly-gained super hearing) that he loves Lois and not her, flies off with ComicBook/JimmyOlsen to their deaths in an attempt to end the villains' attack on his fortress.
-->'''Lana:''' We're only second-stringers, Jimmy, but we'll show 'em. Nobody loved him better than us. ''Nobody!''
** Superman screaming, "YOU HURT LANA?!" was also a GutPunch.
* The Franchise/{{Justice League|of America}} tried to get into Brainiac's shield, but despite their desperate pounding, this battle the Man of Steel would have to fight alone. Think of how sad that would be: TheParagon you always looked up to is in trouble, and all you can do is watch helplessly as his enemies come at him one by one.
* Vartox, who was, in pre-Crisis chronology, engaged in a romantic relationship with Lana Lang, cradling her lifeless body in his arms, bawling like a baby. The man who is too powerful for Superman to contend with. This is a character whose earliest two appearances involved the loss of first his wife, and then his homeworld. When the first Crisis wiped out his existence, this poor bastard was probably grateful...
* "... And by the time I realised where he was heading, it was too late. As he walked into the blinding golden light he turned and looked back over his shoulder. He smiled at me... [[ExactWords I never saw Superman again.]]"
* Even the death of Luthor, as he begs Lana to just end it for him.