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"I wanted this to be professional, efficient, adult, cooperative. Not a lot to ask. Alas, your Mr. Takagi did not see it that way—so he won't be joining us for the rest of his life."

"Do you hear that? Talk to me, where are my detonators? Where are they, or shall I shoot another one? Sooner or later, I might get to someone you do care about."
Hans Gruber, first film
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John McClane and company have faced several threats, but none as vicious, ruthless, and remorseless as the following.

Entries in each group are by release date.

All spoilers are unmarked. You Have Been Warned!


Films
  • Die Hard: Hans Gruber is a self-described "exceptional thief" who leads the takeover of Nakatomi Plaza in Los Angeles. A former German terrorist, Hans is focused solely on his own profit, attempting to steal millions in bearer bonds—a plan which involves demanding the release of numerous terrorists worldwide to throw the authorities off. Executing company head Joseph Takagi when he refuses to cooperate, Gruber has a SWAT team wiped out when they storm the building, and when John McClane interferes, Hans murders a hostage who claims to be John's friend and threatens to begin shooting more until he "gets to someone you do care about!" Hans never intends to let any hostages go, instead placing all of them on the roof to rig it with explosives, which he then plans to detonate—killing over 30 innocent people as a distraction—and fake his own death to escape with the bonds. While only succeeding in killing members of the FBI, Hans immediately kidnaps John's ex-wife before attempting to kill her and John in retribution. Ruthlessly devoted to his own profit above anything else and mixing an utter lack of regard for human lives—even those of his own men—with an air of urbane sophistication, Hans Gruber remains the most deeply personal enemy John McClane has ever faced, and serves as a prototype for countless future action movie villains.
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  • Die Hard 2: Die Harder: Colonel William Stuart is an anti-communist ex-military mercenary, who supported the politics of the cruel dictator and drug lord General Ramon Esperanza. After General Esperanza was imprisoned by US and prepared to be moved from South America to Washington Dulles International Airport to be imprisoned, he paid Stuart to gather up a squad of ex-soldiers and free him. To achieve this, Stuart organized the takeover of the airport, taking control of all the systems and rendering the planes above the airport—one of which carried McClane's wife—unable to land in a strong snowstorm. Holding the entire airport hostage, Stuart became angry when the airport tried to regain control of their systems, acting against his orders; in retaliation, Stuart caused a plane to crash, killing 230 people. Killing several more people, Stuart is determined to get his cash, at one point not even lifting a finger to help his old friend and partner Major Grant in his fight against McClane and ready to cause hundreds of more deaths if the airport refuses to follow his demands.
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  • A Good Day to Die Hard: Alik is a Russian mercenary hired by corrupt Russian official Viktor Chagarin to kidnap Yuri Komarov from the court and extract from him the files which contain compromising information about Chagarin. To this end, Alik sent several of his people to carry in their cars bombs near the courthouse in cars, only to blow them up with his henchmen still inside, killing dozens of innocent people in the courthouse. When John McClane, Jr. has taken away Yuri from his grasp, Alik starts chasing him across the whole city, endangering countless lives and even killing several bystanders, laughing at all the mayhem that was happening around him. Capturing Yuri, Alik tried to sadistically and slowly kill John McClane and John McClane, Jr., beating them for fun.

Video Games

  • Die Hard Trilogy 2: Viva Las Vegas: Kenny Sinclair is a former NYPD cop and friend of John McClane who was always jealous of the latter's seemingly endless luck and decided to kill him, taking control of Las Vegas along the way. Inviting John to his party in Mesa Grande Prison, Kenny organized a prison outbreak, which endangered the lives of dozens of innocent guests at the party and led to deaths of several guards. Hiring mercenaries and ordering them to put bombs all over the city, Kenny also hired terrorists to try to unleash a biological virus in Las Vegas, at one point ordering his partner Reese Hoffman to send his secretary Elena Goshkin to lead the terrorists to try to blow up a city dump and poison the water supply.
  • Die Hard: Vendetta:
    • Piet Gruber is the son of Hans Gruber and a powerful businessman, who organized the stealing of several valuable paintings, killing dozens of people along the way, solely to sell them to Japanese criminal lord Sumi Kazawa in exchange for a prototype RDXS Ample rocket weapon, planning to threaten to destroy the Los Angeles International Airport with this weapon unless he gets 1 billion dollars. As John McClane interferes with his plans and captures one of his associates, Piet leads an attack on a LAPD police station, killing countless innocent cops and then killing his associate, while also trying to blow up the police station itself.
    • Jack Frontier, originally known as Jack Frontslovsky, is a former CIA operative, who left the service to become an actor. After one of his movies flopped, Jack grow angry with the studio replacing him with another actor for Galaxy Thief III. Disappearing for a while, Jack allied himself with Piet Gruber, helping him in his schemes, killing several people along the way and starting a gang war. Eventually betraying Piet, Jack leads an attack on Holmes Observatory in Hollywood at the premier of Galaxy Thief III, setting bombs all around and inside the building, planning to kill everyone there, simply as revenge for replacing him with another actor.

Other Media

  • Nothing Lasts Forever, by Roderick Thorp: In this novel which the original film was based on, Anton "Little Tony The Red" Gruber is a terrorist known for targeting industrialists and executing them. Taking over Klaxon Oil's building in LA, Gruber executes several of the executives and holds 75 hostages there, with only Joe Leland stalling his plans. Gruber eventually guns a hostage down trying to get at Joe, while revealing his true plan is to escape and detonate his explosives to wipe out the hostages, the building and everything and everyone half a mile all around in downtown LA.
  • Die Hard: Year One comic: Alan Douglas is a hippie and Eco-Terrorist, who was a former employer of millionaire Walden Ford, before growing jealous of the latter's rich status and deciding to rob him of his millions. Getting himself a mini-submarine, Alan orders his henchmen to take Ford's yacht full of people hostage, using the fireworks during the 1976 bicentennial celebration over New York Harbor as a cover. As his men kill innocent staff inside the yacht, Alan extracts a large amount of money from Ford and orders his men to plant dynamite on the yacht, planning to blow it up, along with dozens of innocent people on it.

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