Cinema’s Silliest Undercover Assignments

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Movie police work means a lot of doughnuts and drudgery, but every once in a while an assignment comes along that’s so covert its own mum wouldn’t recognise it. All those hours of tedious footslog and stakeouts in sweaty Buicks can pay off in an intense corner of the criminal underworld. One minute you’re pushing paper at the precinct; the next you’re in an Italian restaurant hugging a large man called Frank. But it’s dangerous and disorientating business - as 21 Jump Street reminds us - and you’re going to need to keep your wits about you and a disguise handy at all times. Follow the example of these movie cops and you may just stay alive. And if you’re lucky, you might even get a cheap gold watch at the end of it.

Undercover ‘tecs: Trouble-attracting FBI men Kevin Copeland (Shawn Wayans) and Marcus Copeland (Marlon Wayans)

Mission: To protect highly-kidnappable heiresses the Wilson twins by impersonating them in their Hamptons hang-out and infiltrating their social network. Also: to make True Identity look like Citizen Kane.

Disguises: Full drag and prosthetic make-up. Amazingly, none of the heiresses’ friends bat a heavily made-up eyelid at these giant vulcanised Olsen twins in their midst.

Likelihood of death? High. If they’re not terminated by the baddies, the undercover Wayans face perishing at the hands of furious cinemagoers.

Undercover ‘tec: Rookie FBI agent Johnny Utah (Keanu Reeves)

Mission: To bring down a gang of bank robbers, the Ex-Presidents, led by mysterious blond Zen-machine Bodhi (Patrick Swayze). Thanks to movie science, the posse’s likely whereabouts is narrowed down to a single LA beach. Utah must infiltrate them using surfing and gnarly dialogue – this turns out to be awesome. Thanks movie science!

Disguise: Not a physical disguise so much as a spiritual one. Utah lays on the surf wax and tantric calm thick enough to win Bodhi’s trust… or does he? [Spoiler: he does.]

Likelihood of death? Bodhi’s larcenous layabouts don’t look like the kind to shoot a guy in cold blood – at least not without lighting a few candles first – but try getting life-insurance for all that parachute-free skydiving and big swell action.

Undercover ‘tec: Cincinnati cop Russell Stevens (Laurence Fishburne)

Mission: To pose as a low-level drug dealer in coke kingpin Anton Gallegos’ LA organisation and bring it down from the inside. He’s the Trojan Fishburne.

Disguise: Stevens has to blend in on the street and keep a low profile, which is no easy business when you’re Morpheus. The answer? More denim than Dexy’s Midnight Runners, a lot of visible chest hair and some very serious facial expressions.

Likelihood of death? Stratospheric. If you’re familiar with the genre, you’ll know that death on the streets comes in many shapes and guises: being shot, getting knocked down by a speeding car, death by drug addiction, and getting squished by a flipping Bat-truck to name but a few. Fishburne could suffer any of these. Apart from the last one.

Undercover ‘tecs: Bickering ‘70s cops David Starsky (Ben Stiller) and Ken ‘Hutch’ Hutchinson (Owen Wilson)

Mission: To take down Bay City’s nefarious drug overlord Reese Feldman (Vince Vaughn) and his not-quite-as-nefarious-but-still-not-exactly-Bambi cohort Kevin (Jason Bateman). To do this they must sneak into Feldman’s charity party incognito and find his cocaine stash…

Disguises: ...which they’d manage if their Texas oilman disguise didn’t make them more cognito than Larry Hagman in a neon tutu. Starsky’s turn as Maury “Do it!” Finkle of Finkle Fixtures has novelty on its side; Hutch just looks like he’s had a fight with a fancy-dress shop.

Likelihood of death? Minimal. Only innocent bystanders are in grave danger when the doofus duo is around. During the course of their investigations they manage to shoot a pony, a car and another police officer. The pony isn’t even armed.

Undercover ‘tec: Louis Burke (Jean-Claude Van Damme), a cop whose partner was killed by pitiless baddie the Sandman (Patrick Kilpatrick).

Mission: To go undercover as an inmate at Harrison State Prison and get to the bottom of a murderous organ-harvesting ring. To kick a lot of people in the face.

Disguise: Shirts. Tight shirts.

Likelihood of death? When you’ve beaten Bolo Yeung into the middle of next week, there’s not too much to fear out there. That said, bruising jailyarders and brutal screws would probably make the cut, even for JCVD, a man who does the splits for fun.

Undercover ‘tecs: LAPD partners Joe Friday (Dan Aykroyd) and Pep Streebek (Tom Hanks)

Mission: To crush robe-fancying secret society P.A.G.A.N. (People Against Goodness And Normalcy), a hive of crime, human sacrifice and general naughtiness, while filling all our lives with ‘80s comedy goodness.

Disguise: As another undercover double-act, this time the classic punk and, um, hairnetted pimp combo. We think. Okay, we’re not sure what the Friday/Streebek plan is, other than to look strange enough to deter the suspicious revellers at the P.A.G.A.N. knees-up.

Likelihood of death? Reasonably high. The bad guys have a giant snake. They probably know where you can get more giant snakes.

Undercover ‘tec: Sean Archer (John Travolta), an FBI Special Agent thirsting revenge for the death of his son.
Mission: To track down and apprehend terrorism poster boy Castor Troy (Nicolas Cage). Then to ascertain the location of a bomb that’s he planted by going into prison disguised as him and tricking his brother. Failing that, to kill them. A lot.

Disguise: Not a disguise per se, more an exchange of faces. This is done via an experimental surgical procedure that fortunately doesn’t leave Archer with a wonky Picasso face. Do not try this at your next fancy-dress party.

Likelihood of death? Almost guaranteed. Troy is “the most dangerous and brilliant criminal mind” Archer has ever known, even with his normal face missing. His answer to everything is to shoot someone. Then there’s the small matter of surviving in the joint as an FBI agent.

Undercover ‘tec: Police Squad lieutenant Frank Drebin (Leslie Nielsen)

Mission: To prevent terrorist Rocco Dillon (Fred Ward) blowing up the Academy Awards. Because this is the days before waterboards and Homeland Security, Frank’s task is to cosy up to Dillon to uncover the plot. The catch? He’s in prison.

Disguise: ‘Convicted-felon chic’. Protective chastity pants for romantic shower encounters.

Likelihood of death? There’s prison breaks, bombs, deadly mothers. As the man himself says: like a midget in a urinal, he’s going to have to stay on his toes.

Undercover ‘tec: LAPD-er Detective John Kimble (Arnold Schwarzenegger)

Mission: To go undercover as a teacher at an Oregon kindergarten, track down a key witness to a murder charge, and try to keep control of a horde of sugared-up six year-olds. The kicker? He’s not allowed to shoot any of them.

Disguise: Plaids, tweeds, suspiciously bulging forearms.

Likelihood of death? Slight. Despite the kids’ diagnosis of his headaches (“It’s not a tooomer!”) and the big bad stalking the neighbourhood, Arnie’s biggest danger is full mental breakdown at the hands of his ‘toon-loving tormentors. If only a T-1000 could stop by to take detention...

Undercover ‘tec: FBI agent Joseph Pistone (Johnny Depp)

Mission: To go deep cover under the alias ‘Donnie Brasco’ by exploiting the mentorship of wiseguy Benjamin Ruggiero (Al Pacino). Once he’s won their trust, to bring down the Bonanno crime family.

Disguise: Depp’s Brasco packs the classic ‘70s Mafioso wardrobe (contents: bankroll, leather jacket, sunglasses, hats, concrete shoes, shinebox, etc.) but the deeper he gets the more he becomes his disguise. Where does Pistone end and Brasco begin?

Likelihood of sleeping with the fishes? High. The New York mafia aren’t known for handy out jelly and ice-cream to pesky undercover cops. Plus, Ruggiero, who in real-life murdered more than 20 people himself, is played by the former Tony ‘say ‘elo to my lil’ friend’ Montana. #yikes