What do you think are the most spiteful things that Superman villains have done?

From the top of my head:

All Star Lex giving Superman a toxic dose of yellow sunlight

Pre-Flashpoint Lex destroying New Krypton

Pre-Flashpoint Lex forcing Superman to relive painful moments like dying from Doomsday, Krypton being destroyed, New Krypton being destroyed, Chris Kent going into the Phantom Zone, Jonathan Kent's death

Pre-Crisis Lex refusing to cure a Lois and Lana of deadly disease all while taunting Superman over it

DCAU Lex doing a false presidential campaign to mess with Superman

Smallville Lex making Lana into a Kryptonite Woman that is deadly to Clark

Arrowverse Lex killing the Supermen of the multiverse during the Crisis of Infinite Earths and replacing Earth-96 Superman as the Paragon of Truth

Brainiac One Million capturing all the Legions that Superman had just saved

Cyborg Superman impersonating Superman to corrupt the Legion

Off-Continuity Brainiac recreating Krypton's destruction

Smallville Brainiac infecting Martha with a deadly disease, paralyzing Lana, possessing Chloe, banishing Kara into the Phantom Zone

Absolute Brainiac unleashing villains & victims to discourage/break Superman like Metallo, Toyman, Chemo, Atomic Skull, Bloodsport

Smallville Zod destroying Krypton and sending Doomsday after Kal-El

Mainstream Comic Zod taking out Superman's eye and spreading Kryptonite that is poisonous to everyone on Earth

DCAU Darkseid killing Dan Turpin and making Superman into a brainwashed pawn

DCAMU Darkseid devastating/torturing Earth, its heroes, and Superman specifically by forcing a Kryptonite tattoo on him depowering him as well

Mainstream Universe Darkseid making the Absolute Universe and thus the events of Absolute Superman's life

Pre-Flashpoint Darkseid "killing" Batman and taking control of humanity with the Anti-Life Equation

Mxyzptlk causing Superman's villains to become more murderous (Whatever Happened to the Man of Tomorrow) leading to Superman's secret identity being exposed, the deaths of Pete Ross, Lana Lang, Jimmy Olsen, and Krypto

Mxyzptlk merged with Aethyr crashing the remains of Argo City into Metropolis leaving it devastated, covered in Kryptonite, and littered with Kryptonian corpses

Generations Ultra-Humanite exposed Superman's secret identity, killed Lois, manipulated and later killed Superman's powerless son to become evil and kill Superman's daughter, framed Superman for killing Lex

Pre-Flashpoint Manchester Black revealing Superman's identity to supervillains and faking Lois' death

I remember reading a reprinted superman comic books in the local public library when I was little, and I remember one pretty short story - could not have been more than an issue or two - where the villain was an ordinary hippie looking homeless person. At first he just appears harmless, but it turns out that he could make anyone do anything as long as he said the word "Please" at the end. I think he had just recently come across this power.

Towards the end, the homeless guy tells Superman to take a slow boat to China to get rid of him. Superman found that he could not do anything but sit in a tiny sailboat as it slowly made its way to China, but found a loophole by using his super breath to propel the boat to China.

Superman flew back and was able to defeat him in some kind of loop logic or something. I don't remember the details, but it seemed like the guy loses his powers and also the memory of having had any powers at the end, because Superman as Clark Kent sees the person begging pedestrians for pocket change.

Does anyone know what issue this is or who the antagonist was? This memory came back to me a few weeks back, and I have been trying to look up more information on it, but I am completely stumped. If at all possible, I would like to read it again.

So I'm rewatching some Superman: TAS and I really like the Unity episode.

Superman vs horror concepts is always hard. Like Superman vs Aliens doesn't work because Superman mogs the Xenomorph usually and they have to go out of their way to really make it feel real.

Compare to Batman vs Predator which is a way easier fight to pace/right.

But Unity does it real well. It's cosmic horror so it's scales better and the threat isn't

"Oh my god this thing will hurt me with it's Kryptonian piercing claws"

It's

"Oh my god this thing took over Smallville and now my parents are in danger".

Also focuses on Supergirl for a POV character which was neat. I always like seeing Supergirl be closer to Superman, family wise.

Anyways, I was wondering what ideas you'd have for a Superman vs Cosmic Horror arc for the comics or if there are any horror adjecent issues that you remember?