Although not the darkest figure in DC's roster of heroes, Batman is certainly no stranger to the macabre.
Whether in the original comics from Bob Kane and Bill Finger (mostly just Finger), or the grimdark tales of the 1990s and 2000s, the Caped Crusader and his allies have either suffered or inflicted some incredible misfortunes that more than leave their mark on character and reader alike.
Now obviously the vast majority of terrible Batman-oriented fates have been inflicted by the character's rogues gallery - because of course they have - but only a select few could truly be classified in that mind-bending, terrifying bracket of being worse than death itself. Even so, a 'select few' is still way, way too many, and is enough to leave you wondering why Gothamites everywhere don't live every day with complete and utter dread dominating their every waking thought.
And it's not just the Joker either. While the Clown Prince of Crime is no doubt one of the most terrifying figures to call Gotham City home, there are others who are arguably worse, with Professor Pyg but one of many villains capable of getting extremely... creative (??), with their crime.
Batman's world is suitably scary, but every now and then it crosses a truly disturbing line...
10. The Penguin Ruins Someone's Life... Just Because - Joker's Asylum
A recurring theme with Batman's villains is that a lot of them are a bit insecure. The Riddler is so desperate to prove himself smarter than the Dark Knight that he arrogantly provides the clues that will lead to his own downfall, but arguably even more fragile an ego belongs to Penguin.
Oswald Cobblepot is part of Gotham's elite, but he was never truly accepted by them for several reasons, the first being that the Cobblepots had a tradition of engaging in some not so moral enterprises, and the second relating to Oswald's birdlike appearance.
Despite this, Penguin has always striven to be a member of Gotham's upper crust, wielding power and influence thanks to his criminal connections in a bid to be considered less of an outsider.
When those first two options don't work however, Cobblepot resorts to violence, as was best relayed in Jason Aaron and Jason Pearson's Joker's Asylum: Penguin, a one-shot comic from 2008.
The story sees Penguin at a fancy restaurant with a date, when he spies a chef laughing in the corner of his eye. Penguin's not sure for certain what he's laughing at, but decides it cannot go unpunished, and proceeds to make Kingpin's destruction of Matt Murdock's life in Daredevil: Born Again look like child's play by comparison - at least if Joker's to be believed (which he usually isn't, but y'know, drama).
Following the date, Penguin buys the building and closes the restaurant, leading to the chef losing his job. Cobblepot then deported the chef's partner to Romania, had his best friend arrested for a crime he didn't commit, and moved a neighbour into the flat next to him to play obnoxiously loud music day and night. He closed this man's local church, the park he loved to visit, and exploited the fact he was a recovering alcoholic, opening up a new liquor store opposite his apartment.
The Penguin literally destroyed this man's life from top to bottom, trapping him in his own personal hell.