10 Classic Undercover Movies

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Over the last few years, USA has become known for producing some of the finest drama on television — cable or otherwise — and summer is the network’s season to shine. Their newest offering is Graceland, a provocative drama about the undercover lives of federal agents. The pilot, which premieres June 6, kicks off with an undercover agent being shot in a drug deal gone wrong, and doesn’t let up from there. It follows a group of DEA, FBI, and Customs (ICE) agents who live together in a Southern California beach house. This may sound more Real World than Miami Vice, but Graceland was inspired by real events, and features enough gritty, drug war action to back up its premise.

By delving into the lives of six undercover agents, Graceland offers a unique take on a classic genre. Hollywood has been making great undercover movies since the days of Prohibition, and in honor of Graceland’s premiere, we’re going to take a look back at ten of the classics.

The Departed

The movie that finally won Martin Scorsese his Oscar, and with good reason. A taut crime thriller about the seedy underworld of South Boston, The Departed is full of the double-triple-quadruple crosses that make undercover movies so electric. To infiltrate the Boston mob, Leonardo DiCaprio goes so deep undercover that only one other cop knows he’s not a criminal. At the same time, Matt Damon is a crook masquerading as an honest detective. As their twin deceptions pitch the Irish mob into all-out war, the viewer has only one thing to say: Are you a cop? I’m not a cop!

Donnie Brasco

Before The Departed, there was Donnie Brasco, a heartbreaking story of an undercover narcotics agent who comes to sympathize with his target. Made in 1997, it gives us Johnny Depp pre-Fear And Loathing, but post-Don Juan DeMarco, turning in a swaggering performance that’s far more naturalistic than his work would eventually become. Al Pacino plays a posturing, pathetic mobster, whose tracksuits and greasy hair fit say “seventies!” so perfectly, that it’s hard to believe this movie wasn’t made just a year or two after Serpico.

Serpico

Speaking of Serpico, has anyone ever made a better movie about a man risking his life while pretending to be something he’s not? The twist in Sidney Lumet’s classic saga of police corruption is that his undercover hero, Detective Frank Serpico (Al Pacino), is pretending to be a regular cop while investigating the endemic corruption that had rotted the NYPD from the inside out. Because Serpico was a child of the ’60s, he lives in a swinging Greenwich Village apartment, where he shows off a very shaggy dog and an even shaggier beard.

Prince of the City

Nearly a decade after Serpico, Sidney Lumet took on another true-life tale of police corruption, telling the story of Robert Leuci, a narcotics agent who agreed to break the cardinal rule of all dirty cops: never rat on your partners. In probably his best role, Treat Williams gives an unstoppable performance as a man whose deception is ripping him apart. At nearly three hours, the movie offers enough ’70s grit to make The Warriors look squeaky clean, and gets bonus points for casting the endlessly likable Jerry Orbach as a bad guy. It’s worth watching to the end, if only to see the nice-guy father from Dirty Dancing flip over a table.

Point Break

Most great undercover agent movies are based on true stories, but Johnny Utah is strictly Hollywood. Directed by Kathryn Bigelow long before she won an Oscar for best director, Point Break is not only better than The Hurt Locker, it’s probably the greatest cops-and-robbers-and-surfers movie ever made. Starring superhunks Keanu Reeves and Patrick Swayze — backed up by Gary Busey, because why not? — Point Break features an iconic skydiving scene that required the stars to leap out of a plane dozens of times. And as the English constables of Hot Fuzz know all too well, you’re just not a police officer until you’ve fired your gun up in the air while shouting “aaaaargh!”

Hard Boiled

Is there any sub-genre with a better name than “Hong Kong Blood Opera”? These stylish gangster flicks found international popularity in the early ’90s, and it was Hard Boiled that established John Woo as the master of the form. Although there is an undercover storyline in here somewhere, the film’s plot is more-or-less incidental. (I’ve seen it five times and still don’t really know what it’s about.) What matters is the action — slow motion, double-barreled chaos not too far removed from Sam Peckinpah. The opening shootout is one of the finest ever put to film.

Face Off

For those adrenaline junkies who don’t have time for subtitles, another John Woo classic should fit the bill. One of Woo’s first films made in the United States, Face Off is the best expression of his uncompromising, two-fisted style. When FBI special agent Sean Archer (John Travolta) learns that a comatose terrorist (Nicolas Cage) has planted a bomb somewhere in Los Angeles, he goes as far undercover as is possible — undergoing a face transplant in order to impersonate his captive. But when Cage wakes up, and takes Travolta’s face for his own, what started as a compelling undercover story turns into one of the wildest of all time.

White Heat

A good undercover movie makes you sympathize with the detective and his prey. In White Heat, that’s not so simple. James Cagney plays one of old Hollywood’s most sinister gangsters: a gun-crazy psychopath whose hobbies include beating up his girlfriend, killing g-men, and running to his momma whenever he gets into trouble. While on the run from a nationwide manhunt, Cagney finds that a federal agent has infiltrated their gang, and reacts with characteristic good humor. Best known for the famous final scene, which taught kids of all ages that guns and gasoline do not mix.

Reservoir Dogs

It’s not until halfway through Quentin Tarantino’s first movie (and, I would say, his best) that we know the bloodsoaked Mr. Orange (Tim Roth) is an undercover cop. Needless to say, his infiltration of this gang of well-dressed bank robbers has not gone as planned. Not only has their robbery turned into a bloodbath, but the detective finds himself growing attached to surly, well-tipping gangster Mr. White (Harvey Keitel). Worst of all, he’s stuck in the middle of an empty warehouse with Mr. Blonde (Michael Madsen) — an ear-slicing lunatic who makes James Cagney look sane.

The Spy Who Came In From The Cold

Of course, not all undercover movies are about cops. This film adaptation of the book that made John le Carré famous stars Richard Burton as George Smiley, a rumpled anti-James Bond who prefers cardigans to tuxedos and a pint of bitter to a vodka martini. As part of an elaborate scheme to infiltrate the East German intelligence system, Smiley fakes a nervous breakdown, losing his job and disappearing into an alcoholic fugue in order to make the Soviets think he is looking to defect. While filming, the erratic Burton disappeared completely into his character, refusing to take off his raincoat or sober up for nearly the entire shoot.