7 Great Law Enforcers Who Went Undercover

Jonah Hill and Channing Tatum in 21 Jump Street
(Image credit: Sony)

I’m not a police officer. I didn’t grow up hoping to wear the blue uniform, and quite frankly, there’s about a thousand jobs I’d choose before it. It takes balls, relentless aggression and that weird cop personality quirk to serve and protect successfully. So, for the safety and well-being of not only myself but every other American citizen, I elected to write stories like this instead, but just because I’m absent the skills to effectively enforce codes of conduct doesn’t mean I don’t understand why someone else would attend the academy. I’m sure there’s a whole lot of fulfillment to be found in locking criminals away and patrolling the streets. Working undercover however is a special kind of crazy that I can’t even comprehend.

It takes a borderline sociopath to pretend to be an entirely different person day-after-day. The ruse would drive most people to madness or at least convince them to act foolishly. Don’t take my word for it though, ask movies. Hollywood has been depicting these subterfuges for decades, and nearly every one of these poor characters has had a mental breakdown, downward spiral or intense, what-the-fuck-am-I-doing monologue. As I said before, I don’t know what the hell they’re doing either, but I’ll gladly keep watching their stories on screen.

A week from now on March 16th, Jonah Hill and Channing Tatum are poised to take

21 Jump Street

wide. The early buzz has been very good; so, in honor of their future exploits, here are seven of Cinema Blend’s favorite law enforcement characters who went undercover…

Mr. Orange In Reservoir Dogs

It took time for Freddy Newandyke to learn the lingo, time to perfect his story and time to get close to mastermind Joe Cabot. He strenuously worked to get himself to laugh at the right jokes and speak with the right inflection in his voice, but all of that training must have felt useless as he slowly bled to death in the warehouse following the botched robbery. I love his impassioned pleas to Nice Guy Eddie, hopelessly trying to convince him Mr. Blonde was planning to steal the diamonds, but even more, I love his final confession to Mr. White. He knows it’ll earn him a bullet, but somehow, that’s okay.

John Kimble In Kindergarten Cop

An ability to blend in is typically the most important quality in selecting an undercover officer for a particular job. That’s why O’Hara was originally supposed to be the teacher in Kindergarten Cop, but when circumstances impaired her ability, good ‘ol Arnie came in to achieve absurd, yet solid results. Kindergarten Cop might not be the greatest movie ever, but it’s sure as hell memorable. “It’s not a tumor!” remains a great quote, and I’ll admit I still get satisfaction out of seeing Kimble’s classroom management techniques. All in all, I’m glad this character exists, and I’ll watch Kindergarten Cop three or four more times before I die.

Johnny Utah In Point Break

This movie never would have worked without Keanu Reeves. I’m not sure there’s another actor in the world that could so believably be sucked into a world populated by bankrobbing, philosophizing surfers. If John Kimble was the worst possible pick to play a Kindergarten teacher, Utah’s assignment here is on the exact opposite end of the spectrum. It’s right in his wheelhouse, and I still love watching every over-the-top, kind of buffoonish minute. It’s like all the director’s suggestions were “go a little harder on this take”. Everyone did, Keanu Reeves included, and the result is a masterpiece of fun excess that will probably be played on television periodically until we’re all dead. Vaya con Dios.

Billy Costigan in The Departed

The Departed features numerous characters pretending to be things they’re not. Were this a list of FBI informants, rogue officers or morally complicated badasses, numerous personalities found here could readily apply, but as undercover cops go, Billy Costigan is one of the greats. Throughout The Departed, he’s an absolute mess. The depravity of both the police force and the South Boston mob alter his own moral code, but somehow, he still remains brilliant at his job. When it all goes to hell in the film’s final act, his success only becomes that much more clear. I don’t envy the emotional toll it took on him, but I sure as hell envy his competence.

Gracie Hart In Miss Congeniality

It might be more dangerous to blend in with ruthless drug dealers and vindictive mobsters, but I can’t imagine it’s any more difficult than passing yourself off as a beauty queen. FBI Agent Gracie Hart might not have all the mannerisms down, but by the end, she’s learned enough to not make a scene when Miss Rhode Island describes her perfect date as April 25th. Like Cady Heron found out in Mean Girls, Gracie Lou Freebush grows to both despise and love the beautiful women she’s surrounded with, and while I’m not sure there’s an enlightening moral lesson in that, there’s certainly a watchable movie.

Joseph D Pistone In Donnie Brasco

There are consequences for ratting on your friends, consequences for both you and the people that trusted you. Made men and associates have lived and died by that code for centuries. You would think law enforcement agents would be immune from feeling the sting of breaking omerta, but when Joe Pistone goes undercover in the Bonanno Family as jewel thief Donnie Brasco, he sure as hell quivers at the thought of flipping on his new associates. His buddy Lefty Ruggiero might have killed a shitload of people, but he’s also a good dude that’s in some ways better and more honest than his new friend that’s slowly walking him toward disaster.

Sean Archer In Face/Off

Let’s just admit it right now. Face/Off is ludicrous. In a long career that includes wild shit like Con Air and Drive Angry, it’s probably the craziest Nicholas Cage has ever gone. Given that the whole concept of going undercover is at least a bit odd however, there’s no way I could possibly leave Travolta’s Archer off. The reckless abandon he shows in grafting someone else’s face onto his own is a borderline death wish, a testament to how much he hates bombs, a giant fuck you to his mortal enemy Capser Troy or some combination of all three. Regardless, it’s bizarrely good police work and utterly fascinating to watch. I’m not sure I’d invite Archer to dinner, but I would pay him to spy on my foes.

Honorable Mentions

Pep Streebek in Dragnet, Frank Drebin in Naked Gun 33 1/3: The Final Insult, Malcolm Turner in Big Momma’s House, Brian O’Conner in Fast And The Furious.

This poll is no longer available.

Editor In Chief

Mack Rawden is the Editor-In-Chief of CinemaBlend. He first started working at the publication as a writer back in 2007 and has held various jobs at the site in the time since including Managing Editor, Pop Culture Editor and Staff Writer. He now splits his time between working on CinemaBlend’s user experience, helping to plan the site’s editorial direction and writing passionate articles about niche entertainment topics he’s into. He graduated from Indiana University with a degree in English (go Hoosiers!) and has been interviewed and quoted in a variety of publications including Digiday. Enthusiastic about Clue, case-of-the-week mysteries, a great wrestling promo and cookies at Disney World. Less enthusiastic about the pricing structure of cable, loud noises and Tuesdays.