An FBI Special Agent’s 5 Favorite Undercover Films

Daniel Radcliffe in Imperium

I recently had the pleasure of helping writer-director Daniel Ragussis craft the story for a new film called Imperium, starring Daniel Radcliffe as an FBI undercover agent sent to infiltrate white supremacist groups.

I had worked undercover in extremist groups during a 16-year FBI career, written a book called Thinking Like a Terrorist, and worked on counterterrorism policy as a researcher and civil rights lobbyist.

So it was a topic I was more than familiar with. I’m also a big movie fan, so I had a pretty good idea of what I liked and didn’t like in films that had covered similar ground.

My five favorite films featuring undercover government agents include a couple of obvious ones, and a few that I don’t see listed elsewhere very often. I have to say, having lived this extremely odd existence for many years, a high degree of realism is a must to make my list (at least emotional realism — this is the movies after all).

So as much as it might be obvious that a Southern California-based former agent would go with Point Break, seeing college football star Johnny Utah go undercover in his true identity was kind of an original sin I couldn’t get over (though my early attempts at surfing turned out every bit as ugly as his).

Let’s start with the no-brainers:

#5: The Departed

It has a great director, great cast, great writing, and great performances, a hard combination to beat. Leonardo DiCaprio captures the paranoia that often creeps in during an operation, where an undercover agent’s narrow perspective makes it hard to understand — or trust — that agency decisions about how or when to end an operation. As an advocate for reforming intelligence policy I love Alec Baldwin’s throw-away line about loving the Patriot Act.

#4: Reservoir Dogs

I love a film where you’re trying to solve the mystery with the characters. Tim Roth and Harvey Keitel manage to capture the ambiguity of a very real relationship that can develop despite being built on an intentional deception, and the pain of deception. These two films are great, and don’t top the list only because of the high degree of violence. Don’t get me wrong, I like well-scripted violence in films as much as the next guy (even the infamous Reservoir Dogs torture scene). It’s just who is on the receiving end of the violence in these ones that is a bummer for a real undercover agent.

#3: Eastern Promises

Viggo Mortensen puts in one of the best bad guy performances ever, so good it makes it hard to believe it’s a performance, which it is, of course. A performance within a performance, really. He would have made an excellent undercover agent. And Donald Sumpter was perfect as the case officer overseeing the operation. His emotional turmoil is exquisite in the scene where his plea to end the operation is rejected, capturing the horror involved in wanting to pursue an investigation despite knowing he’s putting a colleague back into a life-threatening situation. Could his ambition to make a big case really be worth the risk of getting his subordinate killed? You betcha. It’s a decision literally made every day, and thankfully there are some talented undercover agents capable of managing those risks with nothing to protect them but their wits.

#2: No Way Out

This one is somewhat of a curveball, much like the film itself. It’s a political thriller about the Secretary of Defense’s attempt to cover-up his accidental killing of his mistress by framing her unidentified boyfriend as a KGB mole within the Pentagon. Kevin Costner puts in what I think is the best performance of his career, playing a young Navy officer assigned to lead the investigation to find the mole. The twist is he quickly realizes the Secretary’s dead mistress is his girlfriend, so he’s searching for himself. KGB undercover agents count, right?

#1: The Molly Maquires

Finally, my favorite movie about undercover agents is the 1970 film, The Molly Maquires, starring Richard Harris and Sean Connery. First of all, Richard Harris and Sean Connery, right? It is a psychological thriller about a Pinkerton detective (Harris) going undercover to identify the leader (Connery) of a group of saboteurs targeting abusive Pennsylvania coal mine owners during the labor strife of the 1870s. Harris and Connery each struggle with the morality of their actions throughout the film, with Harris becoming increasingly haunted by the daily abuse inflicted on the ordinary miners. But the retaliatory violence of The Molly Maguires is equally as appalling. The challenge of reconciling the immorality of answering injustice with injustice leads to a final line that sums up their opinions of one another, and themselves: “See you in Hell.”


I hope you catch Imperium when it comes out on Friday, and find it as exciting and emotionally realistic and compelling as the others on my list.

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