Batman has arguably the greatest rogues gallery in the comic industry, with more than a few ranking up there as some of the best fictional antagonists of all time. But not all of Batman’s bad guys were always evil, as more than a few of his closest friends, family , allies, and sidekicks have broken bad as a direct or indirect result of Batman’s heroics, often getting epic new skills, abilities, and powers, in the process.
Whether by accident, force, or choice that turns them into the worst possible versions of themselves, Batman’s sidekicks have succumbed to dark influences more than once, with the flow of evil doppelgängers never slowing in an infinite multiverse full of them. Here are thirteen canon and alternate earth characters who became major threats to The Dark Knight after they fell to the dark side.
13 Jim Gordon's The Commissioner
One of Batman’s earliest and most integral allies in his fight against the criminal element, Commissioner Jim Gordon turned evil after being infected by the sadistic Batman Who Laughs during the events of 2019’s “Year of the Villain” event. Getting a one-shot tie-in titled The Infected: The Commissioner, by Paul Jenkins and Jack Herbert, Gordon’s corruption saw all the “pain and resentment he holds deep down in his soul” bubble to the surface, making him want to put Gotham out of its misery rather than save it.
12 Alfred Pennyworth’s The Outsider
Once holding the title of The Outsider in a pre-Crisis DC Universe where he was resurrected from the dead with bumpy, chalk-white skin and a bone to pick with the Dynamic Duo, Alfred was eventually saved from this condition by Batman but continued to relapse on occasion until Crisis on Infinite Earths. Not seen again until The New 52 where he was reimagined as the creepy butler of Earth-3’s Owlman, this version of The Outsider is a pale-skinned mastermind who puts together a team of criminals known as The Secret Society of Super Villains on Earth-Prime, effectively warping Batman’s surrogate father into a horrific and unrecognizable baddie.
11 Jenny Wren, the “First” Robin
Considering herself the “first” Robin, Anita Jean aka Jenny Wren, premiered in 2022’s Robins, by Tim Seeley and Baldemar Rivas, and is a previously unknown character who came about during Batman's formative years. Once a sidekick of the villain called The Escape Artist, Jenny worked with Batman to take her mentor down and shoots him dead after he threatens to reveal Batman’s identity. Mortified by her actions, Batman tells her she will never be part of his crusade, leading her to fake her death only to return years later as a honed criminal vigilante who puts Batman’s group of Robins through the wringer.
10 Jason Todd’s Red Hood
Murdered by the Joker while still Robin, Jason Todd returned to haunt Batman decades later as the mysterious villain named Red Hood in the seminal Batman story Under the Red Hood, written by Judd Winick. Getting lethal gun upgrades and taking down criminals with more than a few finely-tuned techniques from his Boy Wonder days, Red Hood toed the line between being a villain and an anti-hero for a while, with fans often forgetting how brutal and deadly Jason was when he first came back to life.
9 Harvey Dent’s Two-Face
One of the most infamous falls from grace in DC history, Harvey Dent was an up-and-coming district attorney making real legal headway in a corrupt city known for its rampant crime and vigilantism, acting as a confidant of Batman’s and personal friend of Bruce Wayne’s. Losing himself to villainy and mental instability after tragically becoming Two-Face, Harvey’s penchant for flipping his coin to make decisions, using his dual pistols with prejudice, and orchestrating the deaths of countless innocent Gothamites made him a far cry from the ally Batman once confided in.
8 Jean Paul Valley’s Batman and Azrael
Jean-Paul Valley debuted in 1992 as the avenging angel known as Azrael and, during the harrowing events of 1993’s Knightfall storyline, became the new Dark Knight after Bane breaks the original’s back. Yet before long, Jean-Paul became an armored brute of a Caped Crusader that was far more violent and mean-spirited than his predecessor. With an advanced weaponized batsuit and a really bad attitude, Jean-Paul was eventually stripped of his Batman role and went back to being Azrael. Unfortunately, and for as heroic as Azrael was at times, the Order of St. Dumas’ brainwashing saw to it that Jean-Paul acted as a villain plenty of times in this role, too.
7 Tim Drake’s Savior
The second identity of a future Tim Drake — one that debuted in 2018’s Teen Titans #15, by Peter Tomasi and Patrick Gleason — this Tim was already acting out of sorts as a murderous gun-toting version of Batman seen in the 2005 storyline titled “Titans Tomorrow.” Later shedding the Batman moniker and becoming a very Midnighter-looking vigilante called Savior, this Tim vows to stop at nothing — including killing even more people — to ensure his dystopian timeline doesn’t come to .
6 Dick Grayson's New Joker
The villain of Frank Miller’s The Dark Knight Strikes Again, this version of Dick was a twisted shell of himself who never got over the abusive tactics Batman subjected him to while training as Robin. Holding a grudge against The Caped Crusader because of this, Dick felt pushed into becoming the second version of Batman’s most hated foe, the Joker, and went through gene therapy surgery to look more like him while acquiring the ability to reconstitute himself from nearly any injury — including getting his head cut off — in the process.
5 Futures Ends' Vampire Batwoman
A version of Kate Kane’s Batwoman from The New 52’s Batwoman: Futures End #1, by Marc Andreyko and Jason Masters, this one-shot flashes forward five years into the future after Kate is bitten by the vampiric villain, Nocturna, and shows her fully lost to her bloodsucking nature. A Batman sidekick who usually works on her lonesome unless explicitly called on, this version of Batwoman gains an insatiable bloodlust, enhanced set of senses, superhuman strength, speed, and reflexes, and even a sweet pair of batwings in her turn to vampirism!
4 Injustice’s Damian Wayne
Part of an alternate world that found a way to distill superpowers into pill form, the journey of Injustice’s version of Damian Wayne is seen in the years-spanning comic continuation of the hit video game series of the same name. A story that shows Damian’s slow fall from grace after he accidentally kills Nightwing, defects to evil Superman’s regime, and eventually becomes the new Nightwing, Damian almost consistently acts as a superpowered thorn in the side of Batman and his underground resistance, becoming far too sympathetic to Superman’s twisted cause for his own good.
