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The Die Hard Villain Power Rankings

by Alex Kirschenbaum Jul 15, 2023

With perhaps the greatest action movie ever turning 35 years young today, I think it’s high time we tackled the eternal question pondered by action fans all across the globe: Hans or Simon Gruber? My answer might surprise you.

That’s right, it’s time for our Die Hard Villain Power Rankings. The immortal action franchise is right up there with EON’s James Bond productions when it comes to churning out a high level of quality baddies per screen minute. Our dedicated panel (of one) is going to sift through the wreckage of the McClane family’s various exploits and identify our top 15 selects from a murderers’ row of, well, murderers.

Given that endearingly flawed wiseass NYPD-turned-LAPD-turned-NYPD cop John McClane (the recently retired Bruce Willis, godspeed good sir) has to navigate around plenty of road blocks while vanquishing various villains, it’s important for the purposes of this list that we define what exactly a villain is here. We’re not talking about antagonists to McClane who ultimately fell on the right side of the law, so irritants like weaselly reporter Dick Thornburg (William Atherton), unnecessarily prickly Captain Carmine Lorenzo (Dennis Franz), and idiotically loquacious cokehead Harry Elis (Hart Bochner) don’t make the cut. Maybe they’ll get their own special Power Rankings in the future.

Given that there are some surprise villains listed here, we’d advise you not to look further until you’ve seen the first four Die Hard movies. As anybody who’s watched it would guess, A Good Day To Die Hard (2013) gets exactly zero representatives in these Power Rankings. I’m also not including any characters from The Detective (1968), the first cinematic adaptation of Roderick Thorp’s series of crime novels covering hard-boiled detective (is there any other kind?) Joe Leland, played by Frank Sinatra in The Detective. Director John McTiernan’s original Die Hard (1988) is an adaptation of Nothing Lasts Forever (1979), the second Leland story, though in the movie Leland is of course re-named John McClane and re-branded as an entirely different kind of character.

That first Die Hard is not in any way a cinematic follow-up to The Detective, and thus we’re counting the ’88 picture as the initial chapter in the McClane adventures here, followed up by a trio of surprisingly worthy sequels: Renny Harlin’s Die Hard 2: Die Harder (1990), McTiernan’s Die Hard With A Vengeance (1995), and Len Wiseman’s Live Free Or Die Hard (2007). Again, the aforementioned, deeply disappointing fifth franchise entry won’t be dwelled on here.

Without further ado, yippee-ki-yay, motherfucker.

15. Mathias Targo (Nick Wyman) – Die Hard With A Vengeance

Before researching his character’s actual name while calibrating this list, I called him “the George Mikan terrorist.” He’s a jumbo-sized, lumbering behemoth who lacks the foot speed of some of his peers, but whose contributions still qualify him for the Die Hard villain Hall of Fame. I feel pretty good about this analogy.

14. Tony Vreski (Andreas Wisniewski) – Die Hard

Also known as the tiny-footed brother (ladies, do the math) of Hans Gruber’s terrifying No. 2, Karl, Tony Vreski was the first member of Gruber’s crew in the original movie with whom John McClane got extended face time. He was instantly ruthless in scouting out our beleaguered, shoeless hero, claiming he wasn’t going to hurt McClane seconds before hopping around a corner and blasting away what he thought was McClane with a machine gun.

Tony’s slippery deceit and his relative awareness of the rules and regulations that should have been restricting McClane’s behavior (“You won’t hurt me… You’re a policeman, there are rules for policemen”) made him perhaps the first truly formidable foe in the franchise canon. And of course, his corpse eventually became iconic in its own right (and a great costume idea for Christmas parties):

14. Mai Linh (Maggie Q) – Live Free Or Die Hard

Our first second-in-command baddie makes her arrival on this list. As the trusted top lieutenant and significant other of McClane’s malicious main foil, Mai Linh is essentially a more flexible martial artist riff on Katya (Sam Phillips) in Die Hard With A Vengeance (don’t worry, we’ll get to her), so she gets points docked for originality. Most known for her dexterity in a terrific elevator shaft showdown against an aging McClane, she died too soon for our liking.

There was a third gorgeous femme fatale faux terrorist in the series, Irina Komarov (Yulia Snigir) from A Good Day To Die Hard, but that movie was so horrific that’s about as much of a mention as it will get in the body of this list.

12. O’Reilly (Robert Patrick) – Die Hard 2: Die Harder

The T-1000 made his first splash in the national consciousness with what amounts to a borderline retroactive cameo here, notable mostly for one killer line reading (“A sitting duck”) as the quarterback for an initial operation to take down an entire SWAT team in an ambush of the skywalk for an unfinished Washington Dulles International Airport terminal.

Patrick is a deep-bench role player in the arsenal of the absolutely psychotic Colonel William Stuart (William Sadler), but even in his limited run here he already exhibits the militaristic swagger and menace he would bring to perhaps the most iconic villain role of the ensuing decade.

11. Katya (Sam Phillips) – Die Hard With A Vengeance

The cigarette-chomping National People’s Army loyalist-turned-mercenary free agent was a woman of few words, but when unleashed was a balletic, artfully lethal assassin so demented in her slaughterings that even Simon Gruber (Jeremy Irons) at times had to curb her rampant bloodlust.

Katya was a long-lasting baddie, though like most of her comrades she seeded most of the fun dialogue and strategizing to her boss/boyfriend Simon.

10. General Ramon Esperanza (Franco Nero) – Die Hard 2: Die Harder

The Die Hard movies are so cool, they roped in Django himself for a cameo!

Playing “the world’s biggest drug dealer,” a corrupt imprisoned leader of a fictive country (“the Republic of Val Verd”) who’s essentially laundering a major narcotics operation through a slush fund, Nero is cool, calm and collected under pressure, an even-keeled co-conspirator along with his more hotheaded U.S. military alums.

9. Thomas Gabriel (Timothy Olyphant) – Live Free Or Die Hard

The mid-2000s were awash with a new breed of contemporary movie villain: the wronged mad genius hacker. Yes, even as far back as the mid-1990s, specifically with Eric Bogosian in 1995’s Under Siege 2: Dark Territory (essentially Die Hard On A Train), this was very much a thing, but with the Internet rapidly moving to the heart of the cultural discourse, this sub-genre of action movie villain saw itself quickly engulfing nefarious character real estate.

Olyphant has long been one of the great on-screen foils, and does a solid job here with a fun if somewhat thin main villain. His Thomas Gabriel may not have the sartorial flair of Hans Gruber or extremist insanity of Colonel Stuart or Major Grant, which is more a function of the writing than any fault of Olyphant’s.

8. Eddie (Dennis Hayden) – Die Hard

The villain I like to refer to as Evil Huey Lewis, who replaces the actual main lobby security guard (Rick Cicetti), Eddie is an excellent two-faced scoundrel, able to toggle between his fake alias as a cynical amateur sports gambler/lackadaisical front desk guard and ruthless, mildly demented Gruber grunt.

I was stunned he survived as far as he did, being the third-from-final baddie to bite it.

7. Uli (Al Leong) – Die Hard

This snack-obsessed Gruber disciple is, like O’Reilly and the George Mikan terrorist before him, a far more ancillary figure than most of the characters who comprise this list (although he survives until the hostages are brought to the roof).

But in his limited screen time, Al Leong (a ubiquitous ’80s action mainstay) still manages to make an indelible impression. While most of the Gruber disciples seem at least somewhat mad, Uli feels far more like a for-hire mercenary: he’s happy to do what needs to be done, but he doesn’t take his work home with him unlike, say, Karl. And if he sees an tasty treat accessible treat during a stakeout, he just might indulge himself.

6. Karl Vreski (Alexander Godunov) – Die Hard

Speak of the devil and he shall appear. Godunov, one of the premier ballet dancers of his day, is more or less the Michael Myers of the first film. Even an extended hanging somehow can’t kill this guy.

It takes a redemptive moment of clarity from desk jockey Al (Reginald VelJohnson) to eliminate the vengeful Karl for good. Though everyone hoped to eliminate the fly in the ointment that was John McClane, the oversized Euro behemoth had been on a singular side quest to personally destroy the NYPD ex-cop after Karl’s brother Tony bit the dusty early.

5. Theo (Clarence Gilyard) – Die Hard

Gruber’s sports-loving tech specialist brings much-needed levity to his moments. Beyond his witty rapport with Hans Gruber as they work tirelessly to crack Nakatomi Plaza’s safe, he also livens up the team’s evening with some superfluous side bets, as when he and Karl are caught betting money on whether or not Mr. Takagi (James Shigeta) will supply his team with the first access code to said safe.

A fun side note: Theo is one of the villains in the entire series to actually survive the onslaught of John McClane. Gilyard would return to antagonize Willis’ McClane in an Advance Auto Parts battery commercial, and although I may not count it as canon per se I still enjoy it a heck of a lot more than A Good Day To Die Hard.

4. Simon Gruber (Jeremy Irons) – Die Hard With A Vengeance

Only Jeremy Irons could convincingly play Alan Rickman’s avenging brother. An inspired casting choice from director John McTiernan, Irons was somehow selected only after The Hunt For Red October alum Sean Connery and David Thewlis turned McTiernan down.

Originally the subject of an entirely non-Die Hard-affiliated spec script, appropriately titled Simon Says, Simon became retroactively transformed into a Gruber after longtime series producer Joel Silver got his mitts on the original screenplay. In an inspired twisty arc for the finished flick, Simon Gruber’s protracted game of “Simon Says” with a very hungover John McClane seems initially to be part of an intricately planned series of mad bombings from a vengeful big brother, before it is finally revealed to be a mere red herring, masking his actual end goal of stealing $140 billion in gold bullions out of the Federal Reserve Bank in Manhattan.

3. Colonel William Stuart (William Sadler) – Die Hard 2: Die Harder

Probably the most vindictive and cartoonishly sadistic of all the Die Hard baddies, the nude tai chi enthusiast Stuart imports a ra-ra discipline straight from his army days to his work as a gleefully murderous mercenary. He’s basically a corruptible Patton.

The character’s vigilant viciousness maybe doesn’t resonate with folks at the same level of the ultra-charismatic and snarky Simon Gruber, but the ex-Special Forces commander’s utter heartlessness (RIP to the crew of the Windsor 114) makes him a more unique antagonist in the franchise. Plus his evil plot is more fun.

2. Major Grant (John Amos) – Die Hard 2: Die Harder

Most Die Hard-heads are furious that I separated the Gruber brothers from occupying the two pole spots of this list. I will concede that I’m a bigger Die Hard 2: Die Harder aficionado than most, but I just enjoy the scheming and style and pure sadism of that more ruthless band of baddies than the goofy gamesmanship of the Irons Gruber.

I’m giving Grant the nod over Stuart here because of his surprise heel turn, which makes him more the emotional center of the story given his betrayal of McClane and co.

1. Hans Gruber (Alan Rickman) – Die Hard

Beyond being just an inimitable quote machine (“And Alexander wept, for there were more no worlds left to conquer,” “SHOOT THE GLASS!,” “That’s a very nice suit, Mr. Takagi. It would be a shame to ruin it,” and “By the time they figure out what went wrong, we’ll be sitting on a beach earning 20%” are my favorites), Gruber’s elegance, wit and arrogance make him probably the single-best action movie villain ever, which is saying a lot amidst this cadre of first-rate creeps.

Gruber became an entire villainous archetype for a generation of memorable movie malevolence. He was ruthless and cruel when he needed to be, but also pragmatic. He wouldn’t arbitrarily murder his henchmen for no reason like, say, Jack Nicholson’s Joker in the next year’s excellent Batman (1989), but he would absolutely leave them to die on a rooftop full of explosives if it made tactical sense for him to achieve his nefarious ends more efficiently in the heat of the moment.

He’s fascinating, too, in the way he stands in stark contrast to the rough-and-tumble John McClane, who’s clearly got very little of his life together while struggling with a marriage on life support, irritating everyone he’s ostensibly working with during the Nakatomi hostage crisis, and accruing grime and bruises in an increasingly more dirty tank top. Gruber, meanwhile, is a man of comparable elegance and taste with a shrewd sense of how to manipulate money and an intricate and convoluted scheme to steal the Nakatomi Corporation’s stash of bearer bonds. He rarely breaks a sweat for much of the movie, even when McClane starts to muck up the works and gets along famously with his crew (at least until he starts letting them die as things begin to unravel). The only personality overlap between the two men is an excellent improvisational cleverness, an ability to pivot planning as their chess games unfolds.

The craziest thing about this all-time heel turn was that it marked Rickman’s first-ever film role. What an entrance.

I know this list is all about the bad guys, but it’s worth mentioning that, without one of the single greatest good guys in action movie history, the whole enterprise could have fallen apart like a deck of cards. Bruce Willis was certainly nobody’s first choice, but in the hands of many of the other actors being considered (Sinatra, Burt Reynolds, Clint Eastwood, Sylvester Stallone, Arnold Schwarzenegger), the John McClane part would have been too superhuman, too impervious to pain.

John McClane, at least in the first three Die Hards, became such a beloved audience surrogate because he seemed all too fallible (he was throwing cars into helicopters by Live Free Or Die Hard). His personal life was a mess, he drank too much, he was in good shape, yes, but not a ‘roided-out superfreak. Heck, he didn’t even have shoes throughout almost all of his first adventure! When he bled, we felt it. When Ah-nuld bleeds, we know it’s not nearly as much as the other guy.

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