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8 Oh S*#t Undercover Movie Moments

Do They Break Cover?

By Dave Richards     November 30, 2009

8 Oh S*#t Undercover Movie Moments
© Bob Trate


Most law enforcement agents can do their jobs with a black and white moral outlook. Undercover agents have no such luxury. An undercover agent must sound, look and most importantly act like a criminal so undercover work is an exercise in morally murky decision making. Undercover agents are constantly wrestling with what actions they can and must do to maintain their cover identity and stay alive. Popular cinema has done its best to try and capture some of these pivotal moments of undercover law enforcers doing the unethical and unthinkable in order to stay alive and take down their target.
What follows are 8 incidents in recent films where an undercover agent had to wrestle with the especially difficult decision of staying undercover and doing something morally difficult or breaking cover. (Beware there may be some spoilers ahead.)

Undercover Movie Plots

8. No Way Out (1987) Directed by Roger Donaldson

Working undercover is a balancing act between digging for dirt and trying not to expose your true identity. In No Way Out, Lieutenant Commander Tom Farrell (Kevin Costner) finds himself walking a particularly treacherous tight rope. His boss, the Secretary of Defense (Gene Hackman) murdered his mistress and the Secretary’s Aide (Will Patton) has concocted an elaborate cover-up that involves Farrell hunting for a fake killer. Engaging in the hunt is both dangerous and disgusting for Farrell, that’s because he was in love with the murdered woman and was secretly seeing her. So Farrell has to decide whether to take part in the cover up and gain incriminating evidence on the Secretary of Defense or break cover and go running to the agency that’s secretly employing him.
The Decision: Farrell decides to play a part in the cover up.
Was it Worth it?: Ultimately yes. Farrell walks away with both the Secretary of Defense's trust and proves that the Secretary committed and covered up a murder.

Undercover Movie Plots

7.The Departed (2006) Directed by Martin Scorsese

An undercover agent has to trust his handler implicitly. They’re the agent’s life line back to the real world. What happens though when your handler is in league with the criminals you’re trying to take down? Undercover Boston state trooper Billy Costigan (Leonardo Dicaprio) finds himself in this very situation near the end of The Departed. He then has to decide whether or not to “come in from the cold” and stay quiet, or go back undercover and work to bring the mob mole in his department down.
The Decision: Costigan decides to go back under cover and use the resources available to him to expose the mole.
Was it worth it?: Ultimately no. No arrests are made and Costigan ends up with a bullet through his skull.

Undercover Movie Plots

6. Running Scared (2006) Directed by Wayne Kramer

When you’re a crook who’s secretly a cop, every choice you make could get you or someone you care about killed. In Joey Gazelle’s (Paul Walker) case that means his wife, his young son, and his elderly father could all wind up in the line of fire. In Running Scared the theft of a gun that Joey was supposed to dispose of for the mob crew he's infiltrated leaves him with the choice of breaking cover and calling in his FBI handlers, or staying out in the cold and trying to both protect his family and take down both his mob crew and their Russian allies.
The Decision: Joey decides to stay undercover and take care of things on his own.
Was it worth it?: Ultimately, no. Joey's decision doesn't lead to any arrests and causes both his young son and wife some severe emotional trauma.

Undercover Movie Plots

5. Eastern Promises (2007) Directed by David Cronenburg

For an undercover agent all that matters is staying alive and gathering evidence against your targets. Your dignity and the dignity of others have to take a back seat. Undercover agent Nikolai Luzhin (Viggo Mortensen) learns this when his superior (Vincent Cassel) in London’s Russian Mafiya orders him to have sex with one of the enslaved women in the Mafiya’s stable of prostitutes. Things get even more complicated with the superior demands to witness the act so he can be certain that Nikolai is not “queer.”
The Decision: Nikolai has sex with the prostitute.
Was it worth it?: Ultimately, yes. Having sex with the prostitute cements the superior's trust in Nikolai and allows him to both save a life later on in the movie and move up the ladder in the Russian Mafiya.

Undercover Movie Plots

4. Donnie Brasco (1997) Directed by Mike Newell

When you’re deep undercover the simplest requests can put both your cover and your life in jeopardy. You either have to do whatever you can to over ride those quests or break your cover. In Donnie Brasco, the title character (Johnny Depp) is faced with a nasty moral dilemma when the owner of a Japanese steakhouse asks him and the members of the mob crew he’s infiltrated to take off their shoes when entering his establishment. The problem is Donnie keeps a tape recorder hidden in his boot and taking it off would reveal it. The restaurant owner won’t back down though so Donnie is left with the choice of either breaking cover in a crowded restaurant or making the owner back down with physical violence.
The Decision: Donnie incites the other members in his crew to give the restaurant owner a vicious beating.
Was it worth it?: Ultimately, yes. Doing so allowed Donnie to stay undercover and deliver testimony and evidence that would lead to over 200 indictments and 100 convictions.

Undercover Movie Plots

3. Reservoir Dogs (1992) Directed by Quentin Tarantino

In Reservoir Dogs Detective Freddie Newandike (To reveal who’s playing Freddie would spoil an important plot point) is placed in the middle of a cop’s worst nightmare. He’s infiltrated a gang of thieves who are desperately trying to discover if there’s an informant in their crew. When one of the more psychotic members of the gang kidnaps a police officer and tortures him for information, Freddie is faced with the dilemma of saving his brother officer and ruining his chance of taking down the gang, or staying quiet and allowing a fellow cop to be tortured.
The Decision: Freddie stays quiet while the officer is tortured.
Was it worth it?: Ultimately, no. Freddie's choice leads to no arrests and things end violently for him and everyone involved.

Undercover Movie Plots

2. Rush (1991) Directed by Lili Fini Zanuck

When you’re posing as a criminal authenticity is very important. In Rush officers Jim Raynor (Jason Patric) and Kristen Cates (Jenifer Jason Leigh) are posing as junkies in a small Texas town in the late ‘70s. They’re tasked with getting drugs off the street and gathering evidence against the town’s drug kingpin (Gregg Allman). In order to appear authentic and gain the trust of dealers Raynor and Cates don’t just have to look like drug addicts they have to act like them as well. So the two begin using drugs and soon they’re consuming just as many drugs as they’re confiscating. The question then becomes do they break cover and get some help? Or do Raynor and Cates stay under and risk the chance of their addictions spiraling out of control?
The Decision: Raynor and Cates choose to not tell their superiors just how bad their addictions are and try to get close to the drug kingpin.
Was it worth it?: Ultimately, no. Raynor and Cates aren't able to get any real evidence on the drug kingpin and the physical and emotional damage of their addictions leave deep scars.

Undercover Movie Plots

1. Deep Cover (1992) Directed by Bill Duke

One of the biggest dangers of undercover work is “going native” and becoming the very thing you’re trying to take down. In Deep Cover, Officer Russell Stephens Jr. finds himself in just such a situation. Stephens is a Cincinnati cop is tapped by the DEA to infiltrate the Los Angeles drug underworld. He assumes the identity of John Hull and quickly rises through the ranks of the drug gang he’s been assigned to take down. At one point in the movie he gets promoted and becomes the organization's chief street dealer, which means he has to move large amounts of drugs. The amounts are so big that Stevens is faced with a choice, break his cover or preserve it by actually selling drugs? Another moral crisis comes when he’s forced to defend his “turf” against a rival dealer and the only way to do so and preserve his identity is by committing murder.
The Decision: Stevens takes over the drug dealing and discovers, much to his horror, that he is quite good at it. And he ambushes his rival in an empty restaurant bathroom where he guns him down in cold blood.
Was it worth it?: Ultimately no. Stevens ends up putting more drugs on the street and none of the targets Stevens was assigned to take down are arrested.
If you look hard enough you’re bound to find more of ethical and ugly dilemmas undercover agents encounter in the world of film. They’re the hallmark of a unique genre and the questions they raise like “do the ends justify the means?” are what makes these morally murky master pieces so compelling.
Speaking of being undercover, check out 10 Unforgettable Werewolf Transformation Scenes

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NotAFan 11/30/2009 3:20:50 AM

Eastern Promises is one of the worst movies I've ever seen!Overrated doesn't begin to cover it! Its a good cure for insomnia!

Lsn22s 11/30/2009 4:52:28 AM

i agree dude...bored me to death, made me laugh at stuff i wasnt supposed to think was funny, and i didnt appreciate the unnecessarily drawn out nude fight scene...ugh wtf...

superrichtheman 11/30/2009 10:09:56 AM

While I didn't need to see Viggo's crank, Eastern Promises was a pretty solid flick. 

SgtTechCom 11/30/2009 10:24:00 AM

Reservoir Dogs best of the lot , Donnie Brasco close 2nd and The Departed # 3 =)

mbeckham1 11/30/2009 11:22:00 AM

You forgot the best example. Wellington Yue. He played an instrumental role in the downfall of House Atreides, all so he coul get his wife back and get Duke Atreides in a position to Assassinate the Barron Harrkonnen.

Was it worth it. Well, yes and no. While his original plan with the poisoned tooth was an almost complete failure, though it did kill Piter Devries, and the Barron Harrkonnen had already killed his wife. However, his other Machinations secured the escape of Lady Jessica and Paul Atreides and the unborn Alia, the latter of who after much planning and attacking by the formers, killed the Barron with a poisoned needle she dubbed the Atreides Gom Jabbar. Thus, granting him his belated revenge in the downfall of House Harrkonnen and the death of his wife's murderer. Though his name would go down in infamy: "A million deaths were not enough for Yue." He would eventually get his revenge, which was the most he knew deep down he would get in the first place.

mbeckham1 11/30/2009 11:40:46 AM

And eastern Promises was Awesome. 

isgrimner 11/30/2009 11:54:42 AM

I thought Eastern Promises was ok for a rental. 

I have trouble taking the list seriously due to #6, Running Scared.  Granted I haven't seen that movie, but that is due to the fact that it stars Paul Walker, who is rather horrible.  I try to stay away from any movie he is in.

animefanjared 11/30/2009 12:36:43 PM

I like that revealing who's the undercover cop in "Resevoir Dogs" is considered too big a plot point to spoil but the list has no problem revealing the ultimate fate of DiCaprio's character in "The Departed."  :-)

ripum853 11/30/2009 2:14:10 PM

He doesn't spoil Costner's true undercover role at the end of No Way Out neither.

SONYMANswallows 11/30/2009 2:52:27 PM

STATE OF GRACE  is better than all of these. Sean Penn joins the Irish Mob while undercover to stop a war between The Irish and Italian Mobs in Hell's Kitchen. Gary Oldman gives his best performance and it makes Drexler look weak. When he turns in his badge to the gang leader is a phenomenal moment.

Davey is misrepresenting Reservoir Dogs  for the sake of this opinion piece. Spoilers in movie that is almost 18 years old? Give me a  break. Kevin Costner is really a Russian and Bruce Willis dead in the 6th Sense. Get over your selves.

And Freddie /Mr Orangec(Tim Roth) hose no sides. He was in shock and showed no spine when Harvey (Mr. White) Keitel killed the approaching cops in the squad car and he did not save his fellow officers. Then his spinelessness causes him to get shot and then kill a innocent woman. Mr White then saves him and takes him back to the hideout.

Losing alot of blood he passes out and wakes up in time to keep Marvin from getting killed  by unloading on Mr. Blonde (Michael Madsen) of course this uses all or most of his bullets and Mr White kills him after everyone else gets killed.


Hey Bruce wayne is batman also.

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