58. The Mother F***er
FIRST APPEARANCE: KICK-ASS #4 (2008) Inspired by Kick-Ass, Chris Genovese, son of mobster John, decides to suit up as a superhero and join Kick-Ass, calling himself Red Mist. In fact, this has all been a plan to gain his father's approval, something that goes awry when his father ends up being killed by Hit-Girl and Kick-Ass, causing Red Mist to begin his descent into pure villainy. Chris eventually styles himself as "The Mother F***er", and amasses a team of villains that hilariously refer to themselves as "The Toxic Mega-C***s", promptly killing Colonel Stars and Stripes and starting a feud with the superhero group, Justice Forever. Things get
really dark, however, when The Mother F***er rapes Katie Deauxma, and ends up having pretty much all of his bones broken when he take a tumble off a roof. He is played by McLovin' himself, Christopher Mintz-Plasse, in the two Kick-Ass movies to date.
57. Saint of Killers
FIRST APPEARANCE: PREACHER (1995) In Preacher, the Saint of Killers is the Patron Saint of Murderers and Assassination, who was a soldier Confederate Army during the American Civil War, and after settling down with a wife and child, was brutally slain after avenging his family's death. Due to his own killing an innocent in his quest for revenge, he is tasked by the Angel of Death with returning to Earth and collecting the souls of those killed under violent circumstances. Kitted out a pair of magical Walker Colt revolvers gifted to him by the Devil - which can kill anything, never miss and have infinite ammo - his first act is to kill Satan with the very guns he gave to him, before discovering that God willed his family to die, resulting in the Saint visiting Heaven, killing a fleet of angels and then putting God down as well. The Saint took the throne for himself, and all was well. Though more ambiguous and sympathetic than most villains on this list, there's no doubting the man's innately dangerous streak, as evidenced by anyone else who dares hold his pistols (which reveals the spirits of everyone he's ever killed).
56. Talia al Ghul
FIRST APPEARANCE: DETECTIVE COMICS #411 (1971) Talia al Ghul is the daughter of Batman's nemesis Ra's al Ghul and one of the more complex adversaries of the Caped Crusader's history, largely because she is also one of the few who is a love interest, having even had a son of his, Damian Wayne, who would later become the fifth iteration of Robin. Much like Bats' relationship with Catwoman, there's a duality to their dynamic, because while Ra's saw Bruce as one of the few worthy of taking his daughter's hand in marriage and assuming his own empire, Bruce is conflicted between his feelings for Talia and his devoting to fighting crime, rather than helping it flourish. In addition to getting the emotional meat hooks in Bruce, she has proven to be an extremely skilled fighter and also a savvy businesswoman and scientist. Though more recent depictions of the character tend to place her less ambiguously along the villain spectrum, she's still one of Batman's most fascinating enemies.