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45 Great Movies About Going Undercover

From cops posing as crooks to men posing as women, this is the definitive list of undercover movies.
Undercover Movies Point Break
By  · Published on August 22nd, 2018

40. Kindergarten Cop

Kindergarten Cop

Like most children who grew up in the 90’s, my introduction to undercover cop movies was this comedy starring Arnold Schwarzenegger a hulking oak police officer posing as a kindergarten teacher. Even as an adult, though, the film holds up spectacularly well as wholesome family fun. At the time, Kindergarten Cop also marked a change of pace for Arnie, who’d primarily featured in macho action fare until then. This showed that he could do comedy as well, and further proved that he is a god among mortals.

39. Beyond the Law

Charlie Sheen In Beyond The Law

Before Charlie Sheen thought he was a rock star from Mars, he was a mere mortal actor who starred in some cool movies back in the 90’s. One of those movies was Beyond the Law, which saw him sport a mullet and pretend to be a biker. In the film, he’s a cop tasked with taking down a gang that specializes in weapons and drugs. Michael Madsen also stars and rounds off a cast of talent who could have been much bigger if they didn’t party so hard irl.

38. Foxy Brown

Pam Grier In Foxy Brown

Pam Grier is the original female action star of American cinema. In the 70’s she paved the way for women to break into the genre and show that they could kick as much ass as their male counterparts. Alongside Coffy and Jackie Brown, Foxy Brown is a career-defining role and one of her best to boot. In the movie, she poses as a prostitute out to avenge the death of her boyfriend who was assassinated by the mob. And you best believe that she don’t take no jive.

37. Miami Vice

Miami Vice Movie

Michael Mann’s adaptation of the 80’s TV series of the same name isn’t on the same level as the original. Nothing really is, though, is it? However, it’s a much better movie than its reputation suggests and functions as a highly-enjoyable crime-thriller in its own right. I suspect this one will also be subject of multiple think pieces when Vin Diesel’s TV reboot arrives in the near future.

36. A Scanner Darkly

A Scanner Darkly

Forget the fact that Alex Jones has a small role in this one. Richard Linklater’s foray into animation, based on the Philip K. Dick short story of the same name, is a treat. Set in the near future, the story follows a narcotics detective who becomes an addict after going undercover to fight the war on drugs. Like Linklater’s other animated flick, Waking Life, The rotoscoping animation makes for one hypnotic and trippy experience. Which is very fitting for a movie about drugs that’s set in the future.

35. Some Like It Hot

Some Like It Hot

The first movie on this list about cross-dressing individuals follows two men who must disguise themselves as women after witnessing a the St. Valentine’s Day Massacre. Of course, when one of the dudes falls in love with a woman, you know it’s only a matter of time before he blows their cover. Elsewhere, the other fella is courted by another man and much hilarity ensues. We have more movies like this to come, albeit not as classy as this one.

34. Coming to America

Coming To America

Not every undercover mission is crime-related. If you use online dating apps then you know first-hand that people occasionally pretend to be someone else in order to find romance. In the case of Eddie Murphy’s character in this comedy classic, it’s because he’s a rich prince and he wants to be loved as a person first and not for his wealth. To accomplish this he pretends to be a broke college student until he meets the woman of his dreams.

33. Stone Cold

Stone Cold

If you’re like me and spend the majority of your free time watching over the top 90’s action movies, then Stone Cold is essential viewing. Bikers check? Shirtless dudes in leather? Naturally. Gung-ho action madness? You’re damn straight! Don’t be put off by the ex-footballer Brian Bosworth in the lead role either — this is campy machismo cinema at its most delightful. Of course, Bosworth isn’t the most charismatic actor on the planet (even for lowbrow action standards), but Stone Cold is pure entertainment all the same.

32. Imperium

Imperium Danielle Radcliffe Shaving

Daniel Radcliffe has come a long way since his Hogwarts days. This is due to his constant desire to take on roles that are challenging and unpredictable. One of the best movies you’ll find in his diverse filmography is this thriller where he plays a FBI agent tasked with bringing down a Neo-Nazi terrorist group. Like most movies involving violent racists, it’s quite disturbing and not for the faint of heart. What’s more disturbing, though, is just how timely movies like this feel in the present day.

31. Gangs of New York

Gangs Of New York

Martin Scorsese‘s epic period crime drama had been 32 years in the making before it saw the light of day in 2002. Inspired by Herbert Asbury’s 1928 non-fiction book “The Gangs of New York: An Informal History of the Underworld”, the story centers around an Irish immigrant who infiltrates a ruthless gang so he can avenge his father’s death. The tale is also set against the backdrop of a tumultuous time for immigrants in the Big Apple, most of whom were poverty-stricken. And while the movie isn’t entirely historically accurate, it has been praised for capturing the panic of the era in which it’s based.

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Kieran is a Contributor to the website you're currently reading. He also loves the movie Varsity Blues.