Black Mask is one of Batman’s most popular foes of the last couple decades. While he isn’t an OG villain, he has the pedigree, debuting in Batman #386 (1985) in the shadow of O’Neill and Adams’s epic restart for the book. He has been a fixture ever since then. Now, he will make the transition to the big screen in live action as the primary villain in Cathy Yan’s Birds of Prey movie.

This is due in large part to his ghastly presence featuring prevalently in print and other media during some of the franchise’s most critically acclaimed moments, including PlayStation’s Arkham series of games and DC Animated features such as Batman: Under the Red Hood and Batman/Superman: Public Enemies. Mask has scratched, clawed, and brutalized his way to the top of the heap of Batman’s rogues’ gallery and the Gotham criminal underworld.

He developed a reputation for ruthlessness right out of the gate that has served him well in his 30 years of existence. In honor (dubious as it is) of his impending arrival on the scene of DC’s Extended Universe, here are five of Mr. Mask’s most dastardly kills and notorious moments.

5. Burning his Parents Alive

When introducing a new villain, you need to give him a compelling backstory and creators Doug Moench and Tom Mandrake did just that.

Born Roman Sionis in his initial incarnation, a product of Gotham’s upper class who turned to crime, Mask had a pretty troubled upbringing. He was dropped on his head at an early age which may have laid the seeds for his eventual dark path. His parents were cold and tough on him, always dragging young Roman reluctantly to social functions to rub elbows with Gotham’s first family, the Waynes, whom the Sionises secretly resented.

Roman began dating a model, Circe, when he entered young adulthood, a relationship his parents strongly disapproved of as unbecoming for their son. This did little to sweeten them to the idea that one day he’d inherit their cosmetics company and run things. Their worry over the prospect proved ominous; not willing to wait, Roman set fire to his parents’ house, killing them. Naturally, the fire ruled an accident, he avoided suspicion and gained control of the family business in the process.

4. The Gruesome Murder of a Wayne executive

Continuing with his first appearance and origin, Mask inherited his father’s company, Janus Cosmetics. However, the callow and unproven Roman lacked the acumen to steer the ship and Janus plunged into bankruptcy and controversy over an untested and hazardous product. The company was soon bought out by Wayne Enterprises and Roman, losing face and his legacy destroyed, turned fully to the dark side.

He broke into his family’s crypt and carved his signature mask out of pieces of his father’s casket. Reborn as Black Mask finally, he recruited criminals to don masks and become his False Face Society. A string of crimes captured the attention of Batman and Mask then perpetrated his first act of revenge against Wayne. Using the untested Janus makeup, he exposed three kidnapped executives to the deadly chemicals contained therein, killing them and ghoulishly melting their faces.

Although Batman managed to stop him, the damage was done and it was only the beginning for the macabre criminal.

3. The Murder of Orpheus

In the 2004 crossover storyline War Games, Black Mask returned to wreak havoc on Batman and become Gotham’s most feared crime boss. One of his gambits involved assuming the identity of third-string vigilante and Bat-family ally Orpheus.

Real name Gavin King, Orpheus sought to make a difference in Gotham and the world after seeing much poverty and suffering as a dancer. When he met with teen hero The Spoiler to discuss how to quell the chaos in Gotham’s underworld and get back into Batman’s good graces, Black Mask showed up and ambushed them.

He took Spoiler hostage to torture her for intel on her plans and slew Orpheus by cutting his throat. Mask then donned the fallen crusader’s costume and successfully infiltrated Batman’s ranks, fooling The Dark Knight. The cold-blooded killer was one step closer to consolidating power and simultaneously demonstrated how dangerous and clandestine he can be.

2. Spoiler’s War Games

Teen superhero and former Bat-sidekick Stephanie Brown, aka the Spoiler, thought she could use one of Batman’s contingency plans for crime in Gotham to fruition. A plan that hinged on bringing all crime lords under the control of Orpheus and Batman and setting up a meeting between them and Matches Malone failed because Malone didn’t show. He is merely one of Bruce’s disguises for sneaking around the underworld, and he wasn’t clued in on his contingency’s initiation.

All out gang warfare broke out and Black Mask saw an opportunity. He kidnapped Spoiler and tortured her into revealing her plans. She escaped and went on the run from Sionis until she succumbed to injuries sustained at the hands of the mad gangster, including a fatal gunshot wound. Black Mask subsequently rose to power in Gotham and made making The Bat’s life a living hell a priority.

1.Feeding the Cat and Family

When it came to Catwoman, Black Mask was one sick, sadistic puppy. In Catwoman #16 (2002)his drug trade caught the attention of Catwoman who decided to steal money from his operation. He wasn’t about to take that lying down, and if we’ve learned anything by now, you don’t mess with the mask. So, in perhaps his most vindictive act of retaliation ever, Black Mask kidnapped Catwoman’s sister, brother-in-law, and friend Holly after Sylvia Sinclair gave up her identity. The brother-in-law was brutally slain and dismembered and her sister was forced into cannibalism of the corpse by Mask, which drove her insane. Mask would continue to terrorize Catwoman and her philanthropic efforts in her community until she fights him at his penthouse.