Black Mask (Batman: Under the Red Hood)

History
Black Mask is the first kingpin to gain control of Gotham in 20 years, having enough influence that he can get whatever he wants, and had drug dealers under his control that he generally kept most of the profits. Five years after the death of Jason Todd, Black Mask had bought the metahuman-based robot Amazo with what was presumably millions of dollars, while fighting against other bidders for the robot including various puppet dictators and psychos who were "as long as [his] arm", and had planned to use Amazo as a means to buy his way up to high-end international trafficking.

However, before he could get the chance to use it, a new criminal kingpin known as the Red Hood had ordered for its theft, with Amazo itself later being destroyed by Batman and Nightwing by having its head blown off during the fight against it. He was left furious at these events, as it meant he was forced to keep rooting around in Gotham, and because Batman tended to keep any wreckage from his fights, he was unable to even sell the remains for scrap, and vowed to have Red Hood killed, saying that "he's dead, take care of him." He then met up with a new recruit to his organization (who had arrived just as he learned the bad news), and after threatening him with cutting his eyes out if he kept staring at his deformities, proceeded to punch him in the face before demanding for a status update regarding weapons shipments, with the recruit informing Black Mask that the weapons cache (this time containing ten cases of assorted SMGs and PDWs, along with 5000 .45 caliber ATG rounds [Black Mask's favorite] as well two cases of RPGs and some cases of C-4) had their dropoff point being redirected as well as security being doubled in light of Red Hood's recent actions. Unfortunately for Black Mask, due to his office being bugged by Batman (and by proxy, Red Hood due to him formerly being Jason Todd), Red Hood learned of this and proceeded to steal the shipments and nearly crash the helicopter.

Afterwards, Black Mask then called his men to his office and then, deciding his previous request was too mired in subtlety, bluntly tells them that he wants Red Hood dead, giving an increasingly graphic description of how he wanted him dead. Although Ms. Lu indicated that they were being careful to monitor any transactions, Black Mask rejected that idea, deciding he intends to have Red Hood learn that this is a "contact sport" by having his men rough up his various business venues to force him out into the open so that when he tries to take them down, he'll arrange to have a "party" meet up with Red Hood (and further elaborating that by "party", he means several assassins wanting him dead).

Ultimately, this failed due to Red Hood calling for Batman's assistance to fight off the Fearsome Hand of Four, with him learning that Red Hood had not just stole his weapons shipments, but also destroyed them, and is also targeting people within Black Mask's province with death instead of recruiting them. Black Mask initially thought this meant he was a more lethal version of Batman, although Ms. Lu corrected him and informed him that more likely, he's just trying to take out his competitors. Black Mask then lashes out at his men, and implies that he knows that one of the Fearsome Hand of Four had been killed due to saying in response to Ms. Lu "Four? Sounds like they need a new name!" while beating his present men down. He also rejects Ms. Lu's suggestion that Batman is simply letting them fight so he could take on the winner, and starts deducing that whatever Batman's reason was for not stopping Red Hood, it had to be something else, realizing they're in the middle of the crossfire. Just then, however, Red Hood attempts to fire a rocket launcher at his office, forcing Black Mask to flee and narrowly avoiding being killed by a fire exit door being flung off its hinges. He then tells Ms. Lu that he's forced into negotiating the release of a psychotic to fight fire with fire against the Red Hood, more specifically the Joker. He makes clear that he was not happy with this and knows its a bad idea, stating it was going to be a nightmare.

He then arranges for several guards under his payroll and killing other guards to secure the Joker's release, and then hires him to kill Red Hood. Although shocked at Joker slaughtering his men, he nonetheless hires him and makes sure he has access to his standard uniform and a truck, as well as some guards. However, Black Mask ultimately is thrown in with the drug dealers that they captured so he could draw out Red Hood and has his life threatened, with him yelling at Joker that him being killed was not part of the deal and demanding his release. Red Hood then arrived, with Black Mask then realizing even his release of the Joker had in fact been part of the Red Hood's plan all along. He nearly ended up burned alive until Batman interfered. He was arrested, although he ultimately was released on bail.

Trivia

 * Black Mask's characterization in the film was significantly toned down compared to the original comic. In the comic, he was prone to have his men extensively tortured if put in a bad mood, as well as gunning them down on a mere whim, while in the movie, he has a tendency to punch his men when left angered due to having a volatile temper.