The 1980s were a landmark time for action films. With actors like Arnold Schwarzenegger and Sylvester Stallone leading the way, action movies shifted to responding to real-world events, or at least using them as settings for telling the stories. Movies like Predator, Commando, Top Gun, Rambo: First Blood, all featured gun-blazing, muscle-rippling, heroes. And by the end of the decade, the action genre took another turn while still using the basic formula of the films that preceded it, with the film Die Hard. Originally pitched as “Rambo in an office building,” Die Hard was something new, but familiar.

Released in 1988, Die Hard was, at its core, about every-man cop John McClane, played by Bruce Willis. Willis was making a star-creating turn on Moonlighting, and Die Hard catapulted him into the same conversations and Arnold and Sly. But, John McClane wasn’t like the characters Arnold and Sly portrayed. He wasn’t a hero already; he was a cop who was caught in extraordinary circumstances. He was smart, but not a genius. He was flawed, but a good man. And he was funny, in his own way.

Die Hard, directed by John McTiernan, was based upon a book called Nothing Lasts Forever, written by former police officer Roderick Thorp, from which screenwriter Jeb Stuart adapted the story. The producers of the film asked that Stuart maintain the Christmas-in-Los Angeles setting, but otherwise was given the latitude to expand the scope. A lot of the main elements and characters are there, but Stuart’s script ended up creating a legacy that has lasted for decades and started a franchise.

And while Willis is the star of the films, a good action movie always needs a villain, and the Die Hard franchise has provided its share of great ones and bad ones, and even more dispensible hired goons. If there’s one thing that rivals the legacy of John McClane, it just might be one of the following villains.

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5 Yuri Komarov - A Good Day To Die Hard (2013)

     20th Century Fox  

The fifth and final film in the Die Hard franchise may have slipped your radar - for which you are not at fault. This entire film is ultimately forgettable. For those that missed it, or don’t remember, this one takes place in Russia and Ukraine. The story revolves around McClane going to Russia where his son, Jack, has been charged with murder. But it’s all a mistake! Jack is actually a CIA operative trying to get info on bad guy Russian, Yuri Komarov, who has compromising information on high-ranking Russian official Viktor Chagarin. But, there’s also Komarov’s daughter! Oh, and she’s actually bad after you thought she was good, but that’s ok if you forgot. The only real memorable part is how Komarov dies, like a block of cheese meeting a grater, as he falls from a roof into helicopter blades. It’s actually a very cool usage of slow motion tied into a tracking shot. But, yeah, Komarov as a villain, like the film, is totally forgettable.

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4 Thomas Gabriel - Live Free or Die Hard (2007)

While this feels more like a regular action movie than a Die Hard movie that just happens to be about John McClane, it’s still a very entertaining movie. Each action scene seems determined to elevate the left of insanity beyond the previous one (the fighter plane vs McClane in a truck is particularly insane). And unlike A Good Day To Die Hard, the villain in this one is good. Played by the excellent Timothy Olyphant, good guy turned bad guy Thomas Gabriel is a villain with intention. Spurned by the U.S. government, Gabriel is set on revenge. He’s definitely evil, without concern for taking life. He’s also smart. His plan very nearly works if it wasn’t for McClane. In fact, of all the near-death moments that McClane has been in, Gabriel might be the villain who came the closest to victory. If it wasn’t for McClane embracing further pain and shooting Gabriel through himself, maybe Gabriel would have won.

3 Colonel Stuart - Die Hard 2: Die Harder (1990)

There’s an argument to be made that the introduction of a villain sets the basis for how bad/ tough/ evil they will be in the movie. For example, the Joker in The Dark Knight, Hans Landa in Inglourious Bastards, and of course - Darth Vader in Star Wars: A New Hope. While introducing Colonel Stuart isn’t nearly as iconic as these examples, it still does a great job of establishing who he is going to be. Any dude who angrily does naked tai chi is probably not going to be a good guy. The film wastes no time establishing his bad guy credentials either. He’s a disgraced formal military officer. He supported General Ramon Esperanza (who is the guy they all work for, but not really the film’s bad guy - there are cases to be made that turncoat Major Grant is nearly as bad as Stuart). Then, once Stuart gains control of Dulles’s operations, to prove his point, he kills hundreds of people when he crashes a British Airlines flight. This dude is BAD. In fact, in terms of body count, Stuart is the baddest of them all. He’s smart, capable, and, like many Die Hard villains, very nearly succeeds, if not for a last ditch McClane effort that thwarts them.

2 Simon Peter Gruber (Die Hard With A Vengeance 1995)

Simon Gruber, or simply Simon in the movie, is the most playful of the Die Hard villains. Jeremy Irons portrays Simon in spectacular fashion. He’s like a cat, playing with the mouse he’s caught before he plans to kill it. Throughout the film, Simon targets and taunts a severely self-destructive McClane. Back in New York, estranged from his wife and family, McClane is a raging alcoholic. When Simon begins his cat-and-mouse game, he positions McClane to die in increasingly intricate ways. Through a wonderful usage of the game, Simon Says, combined with complex riddles and games, Simon leads McClane through a convoluted puzzle - all a ruse to distract from his actual mission. He’s a great villain who keeps twisting the plot and expectations of the audience throughout the film. When it’s revealed that he’s Hans Gruber’s brother, the motivations begin to explore the vengeance behind Simon’s thinking. Emotion clouds his judgments at times, and each time it does, you relish the back and forth between him and McClane.

1 Hans Gruber (Die Hard)

But, no one can compare to Hans Gruber. Portrayed by Alan Rickman in a role that would not only solidify Rickman’s career, but create a template for villains that is used to this day. Gruber is the smartest of the villains of any Die Hard movie. He’s meticulous, he’s calculating, and he’s vicious too. With expert moves, he’s playing the long game in a detailed and extremely well planned caper. He has a team of experts; he’s patient, and he’s able to think on the fly. These things work in his favor as McClane throws wrenches into his operation. Rickman is having a blast as the character too. His ability to slip between his standard English accent, German, and deceive McClane as a frightened American who escaped the party, are uncanny. His one-liners and comebacks are as iconic as McClane’s, and Gruber sets the bar for villains who are moments from victory just before McClane snatches it away.