Entire genres of film exist purely to give us wacky pairings of characters, like a straight cop and a wacky cop, or a white cop and a black cop, or a black cop and a Chinese cop (apparently cops are pretty racist). But often the weirdest partnerships are the ones the movie doesn't seem to think are wacky at all. These are the cohorts and conspirators that, in real life, would have no reason to trust each other with a lunch order, let alone their lives.
6Obadiah Stane and the Terrorists in Iron Man
In Iron Man, Jeff Bridges plays Obadiah Stane, Tony Stark's second-in-command at Stark Industries and the guy who oversees the company's business strategy ... which consists of secretly selling Stark Industries missiles to Middle Eastern terrorists, thereby forcing the government to buy even larger weapons and making a shitload of money for Tony.
Ever since Apple's rise, the bearded lunatic has been a critical component of corporate success.
Eventually, Obadiah grows tired of the "for Tony" part and makes a deal with the terrorists to have Stark executed. However, the terrorists fail to keep up their end of the bargain and hold Tony hostage instead of killing him, forcing him to build a free missile for them. Tony uses the materials to build an Iron Man suit instead and kicks all of the asses.
"We locked a disgruntled weapons designer alone in a room full of parts! How could this have backfired?"
Why It Doesn't Make Sense:
Let's set aside for the moment the fact that Obadiah is a pretty smart guy who still somehow bases his entire plan on the assumption that a bunch of terrorists won't screw him, even though they're, well, terrorists. Maybe they seemed really trustworthy on the phone.
Even then, Obadiah knows that these guys are only in business with him because he has missiles, so he ... sends them the guy who invented the missiles and completely trusts that they won't keep him to themselves? To just make them some missiles? That would be stupid even if his partners weren't terrorists.
And that's the other thing. How exactly was Obadiah planning to keep the company afloat after killing the guy who invents all the weapons?
"We're in the scarf business now."
This isn't like Apple losing Steve Jobs -- Stark Industries is a one-man show. The movie makes a major plot point of this -- when Obadiah asks a team of Stark Industries' best guys to reverse engineer Tony's work, they're completely clueless. Even with his blueprints, computers and all the resources of a huge weapons manufacturing company, they still can't match the work Tony did in a cave.
The reason they couldn't replicate his genius is that all of them were sober.
Worst of all, Obadiah almost thinks they're shitting him when they tell him this, as if he had somehow never noticed that Tony was inventing everything his company sold. Hell, even the terrorists could see that it was stupid to kill Tony, yet apparently it never occurred to the man who worked alongside him for decades.
5Leonard Shelby and John "Teddy" Gammell in Memento
Christopher Nolan's Memento is the inspiring tale of a man with no short-term memory trying to avenge his wife's murder despite his disability. He does this with the help of an annoying sidekick named Teddy, a Polaroid camera and butt tattoos.
Nolan missed a golden opportunity for product placement here.
"Teddy," we later find out, is actually a corrupt cop named John Gammell who has been taking advantage of Leonard's memory problem to turn him into his own personal hit man: He makes "a little money on the side" from every guy that Leonard kills under the impression that he's found his wife's murderer ... only to forget everything and do it again. However, a deliberate misunderstanding causes Leonard to kill Teddy at the end of the movie. Or the beginning. Not sure.
The synopsis is probably carved on our back somewhere.
Why It Doesn't Make Sense:
Actually, Teddy didn't die because of a misunderstanding -- he died because that's what happens when you get yourself an amnesiac assassin. That, or at least jail time.
Even accounting for Leonard's combat skills (presumably a consequence of never being sure if your one-hour exercise routine is finished), the fact that he has no memory still makes him the world's sloppiest personal killer. First of all, he is literally covered in evidence pointing toward Teddy: This is a guy who takes pictures of every single person he meets and permanently tattoos onto his body every thought that goes into his head. Teddy knows that and even teases Leonard about it. There's also the simple fact that Leonard doesn't even remember Teddy, and because of that he never really trusts him.
Also because he betrayed both Neo and Tony Soprano.
Add that general distrust to the fact that Leonard has a huge tattoo on his chest saying his wife's killer is called John G. and we're not sure why Teddy would even want to hang out around him. Presumably Leonard has noticed before that his real name is John and his surname begins with a G. Even with the fake name, it still seems like a ridiculous risk to take, especially when there are hundreds of less intricate ways he could have ripped off drug dealers of their money.
But hey, the fact that Teddy never saw any of this coming means that, at least, his death was no big loss for the police department.
"Man, I should really change my name. To John ... Grey. Yeah."