Ever since taking on Hans Gruber and his band of merry Eastern European terrorists in the original 1988 Die Hard movie, John McClane has been targeted by a bunch of different villains. From a crooked Special Forces commander to a shrill cyberterrorist to a Russian political prisoner, McClane has faced all kinds of antagonists across his five big-screen adventures.
Since Alan Rickman’s iconic portrayal of Gruber set a new standard for action movie villains, every actor hired to play a bad guy in a Die Hard movie has had pretty big shoes to fill. Some of them have come close to matching Rickman’s greatness, while others have fallen short. As some of these bad guys aren't revealed as such until later in their movies, some of these entries might fall into spoiler territory for anyone who isn't all caught up on the Die Hard series.
9 Yuri Komarov
Since A Good Day to Die Hard is more of a generic Bruce Willis actioner than an earnest Die Hard sequel, it’s unsurprising that its villain is a badly written caricature. Yuri Komarov is a Russian political prisoner who is revealed to be the bad guy late in the movie.
Komarov’s role in the plot is to bring McClane and his son closer together, but the movie handles it in such a painfully on-the-nose way when it even bothers to address it at all. The whole Chernobyl-set finale is mind-numbingly dumb on top of it all.
8 Thomas Gabriel
Thomas Gabriel is the cyberterrorist who brings America to its knees in Live Free or Die Hard. His plan is impressive, but he’s let down by being a whiny nerd. The primary objective of a villain is to threaten the hero, but Gabriel never feels like a real threat to McClane.
Timothy Olyphant is perhaps better-suited to roles like smooth-talking antihero Raylan Givens in FX’s Justified and bumbling suburban dad Joel Hammond in Netflix’s Santa Clarita Diet. He didn’t work as well as a snarling villain.
7 Eddie
Eddie is one of the only Americans in Hans Gruber’s band of terrorists, so he’s the one who’s called upon to disguise himself whenever necessary. When Al Powell starts poking around in the lobby, Eddie pretends to be a guard and gets him to go away.
At the end of the movie, when Hans is holding Holly hostage and awaiting McClane’s arrival, Eddie is one of the few terrorists left alive. However, McClane sees to that as he shoots him in the head.
6 Colonel William Stuart
The main villain of Die Hard 2 is Colonel William Stuart, the former Special Forces commander in charge of the takeover of Dulles Airport. Their plan is to liberate General Ramon Esperanza, a dictator from Val Verde.
From his chance encounter with McClane in the airport to their climactic fight on the wing of a plane, Stuart is played memorably by great character actor and frequent movie antagonist William Sadler– even if he’s written as pretty one-note.
5 Karl Vreski
Hans Gruber’s right-hand man Karl Vreski is the one sent to lead the hunt for John McClane when it becomes apparent that there’s a troublesome element on the loose in Nakatomi Plaza.
Karl survives the takeover and very nearly manages to shoot McClane outside the building, but Al Powell manages to shoot Karl in time, redeeming himself.
4 Simon Gruber
At the beginning of Die Hard with a Vengeance, a terrorist threatens New York City and calls on the suspended John McClane for a game of “Simon Says.” Midway through the movie, he’s revealed to be the brother of Hans Gruber seeking revenge for his brother’s death.
Jeremy Irons brought the same charm to Simon Gruber that Alan Rickman brought to his brother in the first movie, while the Gruber connection helped to tie Die Hard with a Vengeance into the larger Die Hard chronology.
3 Mai Linh
While Thomas Gabriel never feels like a real threat to McClane in Live Free or Die Hard, his girlfriend and second-in-command does. Mai Linh is a badass martial artist who’s sent to do all the dirty work that can’t be done with computers alone.
Her fight with McClane in the elevator shaft where an S.U.V. is hanging precariously is one of the most suspenseful sequences in the entire franchise. Maggie Q played Mai Linh before she took on the title role in The CW’s Nikita.
2 Major Grant
Played brilliantly by Good Times and Coming to America star John Amos, Major Grant is introduced as a secondary protagonist in Die Hard 2, recruited to help McClane in his attempts to thwart the bad guys targeting the airport.
However, the sequel comes with the twist that the Special Forces guys are all corrupt. They’re shooting the bad guys with blanks, because they’re in on the plan. So, not only is McClane alone, he has to face a lot more baddies than he thought.
1 Hans Gruber
Of course, Hans Gruber is the greatest villain in the Die Hard franchise. He might even be the greatest villain in the history of action cinema. Alan Rickman brought a devilish charisma to the role of the callous German terrorist who takes over Nakatomi Plaza.
Whether he’s teasing McClane as “Roy Rogers” over the walkie-talkie or pretending to be a lost American hostage when he encounters McClane in person, Rickman is electrifying as Gruber. While younger generations more closely associate Rickman with his role in the Harry Potter series, to older moviegoers, he is forever immortalized as this iconic action movie antagonist.
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