After Bruce Wayne watched his parents gunned down in front of him when he was ten years old, he chose to become the masked vigilante Batman, striking fear into criminals of Gotham City. But many people lose their families to gun violence without becoming superheroes. Bruce had many gifts that set him apart from others, including a vast fortune and genius intellect, but his most significant asset was his indomitable will. Never backing down, he transformed his pain into strength and then inflicted that pain onto the criminals he fought.
However, those same criminals have fought back and caused him plenty more suffering over the years. Batman is tough, but he is still just a man. Unsurprisingly, his greatest enemies are the villains who have caused him the most suffering, torturing him in ways that he will never fully recover from.
Bane
Bane is known as the man who broke the Bat. This is due to his actions in the legendary Knightfall story, where he not only bested Batman in one-on-one combat but broke the hero's spine over his knee. Bruce Wayne would spend the next year in recovery before taking up the cape and cowl again. The two continued to spar over the years, but events came to a head when Bane took control of all of Gotham and seized Alfred as a hostage. Alfred is not just Bruce's butler. He is the man who raised Bruce, acting as a surrogate father. Bane captured Bruce's son, Damian, then made the boy watch as he snapped Alfred's neck, simultaneously killing Batman's father and traumatizing his son in a single act.
Joker
Joker is frequently cited as Batman's greatest enemy. The Clown Prince of Crime considers human suffering to be a hilarious joke and murder to be the ultimate punchline, but there is nothing he considers more fun than hurting his oldest rival. Joker famously killed Jason Todd, the second Robin, by beating him to death with a crowbar. He also once attacked the entire Bat-family, causing Batman to believe that he had skinned their faces. More recently, Joker stole the Wayne fortune and all of the Dark Knight's paramilitary hardware, using them to take over Gotham City. He desecrated both Alfred's corpse and the theater where Bruce attended a movie with his parents before they were killed. Joker used all of Batman's resources against him, turning Gotham into a war zone. In doing so, he made the Dark Knight realize that his entire mission was a failure, or to put it another way, that it was all a sick sad joke.
Joe Chill
Unlike the costumed rogues and masked supervillains on this list, Joe Chill is a common criminal. He is also the gunman who murdered Thomas and Martha Wayne. If not for Chill, there would be no Batman. He traumatized a little boy and killed two people, all for a bit of petty cash. To this day, Batman can still remember the muzzle fire and the sight of his mother's pearls spilling onto the street as Chill grabbed at her necklace. This was probably the first time that Bruce ever had to face the horrors of violent street crime that most Gothamites lived with daily, and it left his world completely shattered.
The Batman Who Laughs
The DC Multiverse includes many different universes, including an entire Dark Multiverse filled with tragic and broken alternate versions of classic heroes. The Batman Who Laughs is a Jokerized version of Batman from the Dark Multiverse. He is every bit as strong, smart and skilled as the original Batman, but with none of the moral constraints. He unleashed other evil Batmen from the Dark Multiverse, threatening to destroy reality itself. But the Batman Who Laughs also reveals the true potential for horror and violence that Batman (the actual Batman) is capable of. While he can pretend to be a hero, when Batman confronted the worst version of himself in the multiverse, he realized that their similarities far outnumbered their differences.
Scarecrow
Scarecrow is one of Batman's oldest and most iconic villains. He normally torments people by dosing them with a special fear toxin, causing them to spiral into panic attacks or even hallucinate their worst fears. Recently, he has taken another approach, using the media to generate mass hysteria and plunge Gotham into a city-wide state of fear. When Batman went to investigate, Scarecrow captured him and dosed the hero with the strongest strain of the fear toxin ever produced. The Dark Knight was bound in a straightjacket and tortured, driven through all the horrors of his life and left completely isolated amid the agonizing trauma of his own mind.
Deacon Blackfire
Deacon Blackfire is a truly terrifying villain, albeit one who has faded into relative obscurity. He made his debut in the story Batman: Cult by Jim Starlin and Bernie Wrightson, in which he tortured the Caped Crusader worse than almost any other villain had to that point. As the leader of a massive cult, Deacon Blackfire used his charismatic influence to manipulate his followers into carrying out violent attacks. He captured Batman, torturing and brainwashing the hero, who suffered ego death as he hallucinated his body melting. Batman lost all sense of his identity, becoming fully indoctrinated into the cult.
The Black Glove
Rather than being a single individual, the Black Glove is a shadowy cabal of aristocratic minor villains who came together to destroy Batman--and they succeeded. The leader of the organization, Dr. Simon Hurt, is actually one of the ancestors of the Wayne family. The group destroyed the name of Bruce's father by falsifying reports of egregious scandals. They took over Wayne Manor and tortured Alfred. They used hypnotic suggestions to turn Batman into a raving psychological wreck. The Black Glove did not kill Batman by putting him in the grave, but rather by shattering everything that made Bruce Wayne capable of being Batman.