Warning! The last entry in this article contains spoilers for The Pengiun season 1 finale.
The world of Batman in live-action extends far beyond the central hero, with a detestable cast of rogues and villains who have committed some of the most disturbing crimes in any comic-book adaptation, especially in the live-action movies and shows. Long before the DCU, Batman starred in live-action TV shows and films alongside having a popular comic book series under the DC Comics label. However, the version of Batman, and alongside him the city of Gotham, has gotten noticeably darker as the adaptations continue.
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Adam West’s Batman was more wholesome, with a cast of colorful villains who were more goofy than ghastly. But when Tim Burton adapted the story, the world of Batman got considerably more dark and twisted. This development continued over the next four decades, taking the character to the point where he remains today in films; a Dark Avenger, and a vigilante who seeks justice through violent, unrelenting means. And as the hero shifts into a Dark Knight, so too does Gotham, and the villains, who become increasingly menacing with each new story.
10 Victor Zsasz Taking Over GCPD In Gotham
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Gotham is a series that ran from 2014 to 2019. As the title suggests, the show shifted the focus from Batman, and instead took a closer look at the corrupt and crooked city of Gotham. While Bruce Wayne appears as a young teenager, who has a keen skill for detective work, he is not yet Batman, and instead, Detective Jim Gordon is left to try and clean up a city with a rotten core.
But despite Jim’s best efforts, even the Gotham City Police Department is filled with dirty cops. This can be seen when Victor Zsasz turns up at the GCPD, stands up on a table, and commands the entire police force to leave so he can “handle” Jim Gordon. The city is deeply corrupt, but Zsasz plays this to his advantage as he walks unimpeded, and unafraid, into a room full of armed cops, and gets his way.
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9 Joker’s Magic Trick In The Dark Knight
The Joker is one of Batman’s all-time greatest rivals, and so it makes sense that the character is viewed as a legend among criminals. However, when the Joker shows up in Christopher Nolan’s The Dark Knight, he appears to be a newcomer to Gotham. The established crime families have no idea who he is, and so, they refuse to give him any time or respect. But, the Joker is able to brilliantly and quickly demand their attention and establish his abilities.
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In a room full of thugs and their guards, Joker asks the table of higher ups if they want to see a magic trick. Looking like a jester in clown makeup, they begrudgingly oblige for a brief moment. Fortunately, a brief moment is all the Joker needs, as he stands a pencil up on a table, grabs one of the guards, and slams their head, eyeball first, into the pencil, killing the man instantly as it pierces his brain. This sudden brutality made it clear that the Joker was an incredibly dangerous rival. But to ensure his escape, he also wrapped himself in explosives, which further cemented his reputation as someone not to be messed with.
8 Arthur Fleck Murdering A Talk Show Host Live On TV In The Joker
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Another version of this iconic character appeared in Todd Phillips 2019 film, Joker. Here, the story outlines an origin story for the Clown King of Gotham, as an unassuming and mentally unwell man named Arthur Fleck slowly descends into madness and unleashes an alter ego known as the Joker. Fleck fantasizes about murder and laughter, as he seeks to fulfill his purpose of making people smile, but finds himself constantly greeted by anger and frustration from the people he meets.
After brutally killing three young men who treated him poorly in the subway, Fleck gets an invitation to his favorite talk show, hosted by his favorite presenter, Murray Franklin. While Fleck admires the man, it only takes a moment before Franklin begins undermining and belittling Fleck. This enrages Fleck, and he transforms from a nervous, frail man into a symbol of anarchy and violence as the Joker. Pulling a gun on the host on live TV, and unloading his weapon into Murray Franklin in front of millions of viewers at home.
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7 Jervis Tetch Capturing Jim Gordon And Murdering A Couple In Front Of Him
Returning to Gotham for a moment, Jim Gordon fought a considerable number of rivals in his time as a fresh recruit to the GCPD. At one point, Gordon is forced to fight an incredibly gifted hypnotist and magician, Jervis Tetch. While most hypnotists may use their talents for entertainment, or to aid others, Tetch behaves in a radically different way.
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The Penguin’s finale saw Sofia Falcone receive a letter from Selina Kyle when she was sent back to Arkham Asylum. Selina reaching out to her half-sister was what Sofia needed to snap out of a depressed state. A knowing smile from Cristin Milioti’s character teased that there is more story to tell between those two. While that could happen in The Batman – Part II, The Penguin’s success will lead to more spinoff shows. One of those could be a Catwoman series, with Zoë Kravitz’s Selina Kyle breaking into Arkham to free her sister, which I would love.
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At one point, Tetch summons Gordon and his partner, Harvey Bullock, to a location where he clearly intends to trap them. However, Gordon does not back down from a challenge, and being aware that the alternative could spell death, he goes. Unfortunately, on this occasion, Tetch has set Gordon up with dozens of hypnotized people who restrain the detective and his partner, as he watches helplessly while a couple, possibly newlyweds, judging by their clothes, stand motionless, before they are brutally murdered by Tetch releasing an enormous wrecking ball.
6 Joker Killing Bruce Wayne’s Parents In Tim Burton’s Batman
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While the comics and animated shows have revealed Bruce Wayne’s parents’ killer to be a man named Joe Chill in most iterations, Tim Burton’s Batman in 1989 established a different origin for the hero. Rather than being some low level criminal, looking for a quick payout and mugging the Wayne’s Jack Nicholson’s Joker was actually revealed to be the killer. This puts the villain into a whole new category as a rival to Batman, as he was literally pulling the trigger on the moment that changed young Bruce’s life forever.
This version of the Joker had high ambitions, and a love of chaos, which could hint at why he was doing such petty crime despite having the potential to be a criminal mastermind, but he built his empire. For this reason, Michael Keaton’s Batman has a particular hatred for the Joker, beyond what most of the other Caped Crusaders ever show. This remains one of the Joker’s most cruel attacks against Bruce Wayne.
5 Ra’s al Ghul Poisoning Gotham’s Water Supply In Batman Begins
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Another notable betrayal of trust came for Christian Bale’s Batman in Batman Begins. In this superhero origin story from Christopher Nolan, Bruce travels the world after his parents’ death in order to find some greater purpose. As a boy, witnessing his parents’ death, Bruce felt utterly powerless, and he was determined to never feel this way again. So, he traveled the world in search of mentors and guides who could shape him into an unstoppable force for good.
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Along this journey, he came into contact with one man, Ra’s al Ghul, who became a close friend and guide on this route when he trained with the League of Shadows. However, Bruce was stunned when he returned home and found himself facing off against his old friend who was now seeking to cause irreparable damage and chaos in Gotham. Over a number of weeks, al Ghul had employed the services of Jonathan Crane, aka Scarecrow, to poison the water supply in Gotham and use a special toxin that would force the citizens into a violent frenzy on his command.
4 Jeremiah Valeska Turning Gotham Into No Man’s Land
Once again turning attention back to Gotham, where some of the most heinous crimes were committed by these villains early in their careers. For one, Jeremiah Valeska was one of the most notable and terrifying villains in Gotham, who succeeded his twin brother Jerome as a criminal mastermind after his brother’s death. Jeremiah took things so much further than his brother, even enacting a similar plan to al Ghul’s above, albeit, much more effectively.
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Jeremiah planted numerous explosives around Gotham, exploding bridges around the city and essentially trapping all the residents inside. Jeremiah killed countless people, sent his cult of followers out into the streets and caused city-wide chaos and destruction. This brutal and torturous act was eventually halted and the city had some time to recover, but for a brief moment, Jeremiah ran Gotham.
3 The Riddler Flooding Gotham And Brainwashing Civilians In The Batman
In Matt Reeves’ The Batman, a similar incident occurs, although another one of the classic Batman villains is behind it. The Riddler, as played by Paul Dano, is a quiet man who has found a group of like-minded believers online. Through extensive research in chatrooms and collaboration with others in Gotham, Riddler was able to coordinate an attack that was so much bigger than him as an individual, and caused panic throughout the city.
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Despite being captured and detained, the disciples of the Riddler get to work on his master plan, setting up charges at a nearby dam, and hoping to trap and kill many of the citizens of Gotham within a large football stadium during a political rally. Due to the sheer number of assailants, these men were successful in flooding Gotham, and causing mass chaos, destruction, and paranoia.
2 The Joker Murdering Rachel And Turning Harvey Dent Into Two-Face In The Dark Knight
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One of the most harrowing acts performed by Heath Ledger’s Joker in The Dark Knight was when he set up Batman and the GCPD to try and save either Rachel Dawes, Bruce Wayne’s ex, or Harvey Dent, the new district attorney who was commonly nicknamed the White Knight of Gotham. Of course, Batman rushed to save his ex, but the Joker caught him in a double bluff, sending him to the wrong location. Unfortunately, by the time he arrived, Dent was already trying to speed up his demise, and suffered intense burns on one half of his body.
Rachel died before the GCPD could rescue her, and this came as a massive blow to Batman, but also Dent, who was her fiancé at the time of her death. With Dent brutally disfigured, and his beloved Rachel now dead, he gave up on his dream of saving Gotham in the right and just way. Instead, Dent turned to fate, and became Two-Face, a brutal killer who doled out justice according to the flip of a coin.
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1 The Penguin Killing Victor After Taking Over Gotham
Image via Max
The Penguin is a spin-off series from Matt Reeves’ The Batman, following the titular villain on his rise to power in Gotham. Over the course of the show, Oz shows how cruel and conniving he can be, as he sets his rivals and competition against each other, but along the way, he develops a close connection with a young man named Victor. Initially, Victor is attempting to take Oz’s car with a group of other low-level criminals, but Oz decides to take Victor under his wing and mentor him. Initially, their relationship is rocky, with Victor struggling to trust the man, but eventually, they become fond of one another.
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Related The Penguin Just Made Oz More Dangerous To The Batman, I Just Hope The Sequel Makes Him The Main Villain
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In the final episode of The Penguin season 1, Oz and Victor sit together, looking over the city that they have struggled together to lay claim to. Oz’s enemies are dead or out of the picture, and Victor shares a touching moment as he says Oz is “like family,” but that only serves to make the next moment so much more brutal and monstrous. Oz locks his grip around young Victor’s neck, expressing affection for the boy, but also stating how he could be a weakness later on, and he commits the ultimate monstrous act for any Batman villain, killing this boy whose trust he earned.
Upcoming DC Movie Releases
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Superman
Release Date July 11, 2025
- Supergirl: Woman of Tomorrow
Release Date June 26, 2026
- The Batman Part II
Release Date October 2, 2026
Superman
Supergirl: Woman of Tomorrow
The Batman Part II
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