#2. Marine Brigadier General Francis X. Hummel from The Rock
In a nod to real events following the first Iraq War, Ed Harris is a Desert Storm vet who's been screwed over by the government for the last time, and sets out to get his just desserts with an operation he totally should have called "Just Desserts Storm."
And just like the real vets who tried to raise public awareness by staging protests and lobbying their representatives in Congress, Harris and his men ... steal missiles full of nerve gas, take all the tourists on Alcatraz hostage, and then threaten to kill every man woman and child in the city of San Francisco unless the US makes with some cash.
Fear not henchmen, Harris has thought this one through. As he explains to his men, "A couple of hundred years ago, a few guys called Washington, Jefferson and Adams were branded as traitors by the British, and now they're called patriots. In time so shall we."
For some reason, none of his men raise their hand here to point out that his plan involves killing a city full of innocent Americans. Or that this will probably be significantly less popular with Americans than the Revolutionary War. Or that you'd probably have a better chance of being called a patriot if you just waited for Ronald Reagan to die, jumped atop his coffin while Nancy was paying her final respects and turkey slapped her across the face.
Mr. Harris of course doesn't need to worry about long-term public perception since his plan unravels long before that. To begin with, it's all an elaborate bluff. Apparently his plan was to give the military a stern talking to, make a bunch of loud noise, get paid money, escape from Alcatraz and presumably ride a unicorn to Never Neverland.
If that second to last phase of the operation, escape from Alcatraz, sounds familiar its because they made an entire movie about the only people who ever did it successfully. The Rock implies Alcatraz is a good place to be when you're threatening the US military because it used to be the site of a military base, but as General Harris would know, the military gave up on using it as a base because it's a tiny shitty island in the middle of a bunch of cold shitty water. It's a great place to stick people you never want to see again, and an awful place to do absolutely anything else.
Why It Failed:
First of all, there are way too many things to keep track of: Invading black-ops teams, hostages, deadly tear gas, the wild card duo of Cage and Connery who are just hilariously mismatched enough to get the job done.
Adding insult to injury, all Harris had to do was wait a few years until the US government got involved in an unpopular sequel to Desert Storm, become an independent contractor and hold them hostage with ridiculous hourly rates.
#1. Colonel Stuart from Die Hard 2
It's Die Hard, so instead of having semi-altruistic motives like General Hummel, Stuart is chasing that elusive Die Hard villain dream: Stealing enough money to buy his very own tropical island so that he can live out the rest of his days in seclusion with a bunch of creepy henchmen.
Die Hard terrorists have utilized increasingly ambitious canvases with each film, from a single high rise in the first to Dulles Airport in the second, New York City in the third and the entire country in the fourth. We're focusing on Stuart because, while not the most ambitious, his plan is certainly the most convoluted. And because the fourth was basically about a wizard who casts spells in computer jibberish, so he doesn't count.
Stuart on the other hand plans to take an entire airport hostage through good old-fashioned clockwork precision. He and his crew walk around Dulles in lock-step with each other, passing guns back and forth in gift wrapped boxes, and constantly checking their synchronized watches. Unfortunately, these aren't great strategies for blending into a crowd, and John McClane's extensive background in Christmas terror plot reconnaissance tells him something's up.
Stuart then overrides all communication between the air traffic control tower and the planes (he probably had an early version of the iPhone) and turns the lights out on the runway by having one of his men chop through a bunch of cords with an ax. If you think these actions are carried out with precision that is anything other than clock-like, you either don't know shit about clocks or Stuart. Or similes.
Now he has the whole country by the balls. With no lights on the runways, Stuart's able to lie to the pilots about their altitude and crash some motherfucking planes! It's truly a diabolical, air-tight plan.
... that only works if there's a blizzard. If it's a clear night the pilots are probably going to see one of the other million lights on the ground that he didn't turn off like the terminal and the air traffic control tower and the parking lot.
But you can't blame Stuart for gambling his entire plan on the one-in-a-million chance that there's a blizzard in Virginia on the day it goes down. He was probably busy with all the other details, like keeping the blank machine gun clips separate from the live rounds so that none of the guys who are working for him shoot each other. You know, during the elaborate fake machine gun battle on snowmobiles. The one that is supposed to throw McClane off their scent. You know, McClane, the guy the trailer specifically says nobody was counting on.
"Man, this plan would have sucked if it had been 20 degrees warmer."
Why It Failed:
It actually went pretty well. Stuart is able to take over the airport, the Pentagon conveniently sends the special ops team headed up by his mentor, a freak blizzard hits the confederate state where his operation is taking place. Also, only one good guy realizes that a huge bonfire on the runway gives the pilots a landing light bright enough to shine through the blizzard, effectively taking away Stuarts only bargaining chip. And that good guy doesn't realize it until the end of the movie.
Of course by that point, Stuart's watched his mentor get shit out the back of a jet engine and is himself used as kindling for the landing light. But, y'know. A for effort.
If you enjoyed that, you might like our rundown of 5 Kick Ass Action Movies That Are Pure Propaganda. Or head to the brand new Official Cracked.com Store and become a startlingly attractive walking advertisement for our site. And be sure to get the Cracked Hit List delivered in your electronic mailbox every Thursday. And be even surer to find out who made the cut in The Week in Douchebaggery.