No one said going undercover would be easy. And if they did, they were lying to you. Wait. Why were you even talking about going undercover in the first place?

Never mind. I don’t even care.

Well, as these seven films demonstrate, going undercover is definitely NOT easy, and as Murphy’s Law dictates, anything that can go wrong will. So enjoy these seven tales of deep cover operatives looking on haplessly as everything goes to hell.


21 Jump Street

Any undercover operation that involves a severed penis does not end well. It’s almost like these police officers are incompetent! Why on earth would the police hire people who can’t do their job well? But it's a pretty funny film, so let’s just forget about all the crappy things that happened to the characters in the movie and be happy for their “success,” ya know?

Reservoir Dogs

Undercover assignments do not get more f*cked up than this one did. When you find a cop tied to a chair, a man dancing to Stealer’s Wheel while cutting the cop’s ear off, and he’s about to light him on fire, it’s time to reevaluate the actions you took to find yourself in that very moment.

Granted, the cop getting the Van Gogh treatment wasn’t undercover, but it’s hard to say that anything in this film really went well for anyone. Here’s the big takeaway: Going undercover is a form of lying, and you should NEVER LIE.

It’s just that simple. Lying is crappy behavior, even to catch bad guys.

Kindergarten Cop

I guess technically this assignment went off without a hitch from the police department’s perspective, but I would say that it was less than spectacular for the parents of the kindergartners. For one thing, the guy wasn’t a teacher. I understand that it’s just kindergartners, but the fact is that these kids are entitled to an education, and Arnold Schwarzenegger is not a certified teacher. Certified badass? Maybe. But not a teacher.

There should have been a waiver that parents had to sign that said “I don’t mind if an undercover cop teaches my child for a few weeks so that he can find a criminal.”

Of course, though, on of those parents was the criminal, so that could have been a red flag.


Rule #1 of going undercover: Don’t get really, really addicted to cocaine. Ok. Maybe “don’t let your badge fall out of your pocket” is rule #1, but “don’t get addicted to cocaine” is pretty high up there on the list of rules. We’ve all seen movies where the protagonist has to kill a guy or snort something to prove that he’s “down.” Well, here’s the fall out. It could have gone either way though. Maybe Jason Patric’s character could have dealt with cocaine in moderation and just become a really run party guy that occasionally did some blow. That didn’t happen though.

The Departed


When pretty much everyone dies at the end, it’s hard to deem your operation a success. Granted, Mark Wahlberg’s character lived, but I don’t think anyone really liked him that much anyway. They did manage to take down Costello, but that was actually the work of a double agent, one of his very own men.

I could spend two paragraphs or so explaining what went down and when, but when you’ve got two moles on different sides chasing each other down to steal a glance at the other person, something has gone wrong. Further, when the psychological toll on the state police operative is so heavy that he’s driven to pills and sleeping with his shrink, maybe it’s time to rethink the corporate culture of the Massachusetts state police.

And finally, police captain’s really shouldn’t get tossed out of windows.

Point Break

Sure, it worked out in the end, but when your FBI agent has to jump out of a plane without a parachute to catch a the ring leader of a bank robbing team, something has probably gone horribly wrong.

On the plus side, this operation allowed operative Johnny Utah to become a pretty good surfer (awesome!) and fall in love with Lori Petty (eh). But that doesn’t outweigh the fact that Utah made the rookie mistake of “getting in to deep,” and becoming not only friends, but weird surfer soul mates with Bodhi and company.

Perhaps if he’d infiltrated a gang of Rollerbladers, he wouldn’t have enjoyed the lifestyle quite so much.

The Bourne Franchise

Damn you Treadstone! If you can’t trust a secret government agency, who can you trust? After seeing all three films, I still have next to know idea of what the original mission was, but considering most everyone got killed and Jason Bourne is leaving and never coming back, I doubt that the U.S. government will chalk this up as a “W.”

They lost a good man in Clive Owen, too!