Boris Grishenko with the best hacker grin

I am deeply obsessed with hacker culture. In my movie watching preferences, this obsession manifests as a deep affinity for hacker movies. Some of my favorite movies of all time are directly influenced by hacker culture such as The Matrix (1999) or Hackers (1995).

In the 1990’s and early 2000’s, there seemed to be a great trend in Hollywood of depicting hacker characters, even in movies that weren’t strictly technology or cyberpunk themed. I absolutely love when these characters appear in movies, and I thought I’d collect a few of my favorites here.

I’m purposely omitting some of the obvious ones, such as any characters from The Matrix (my favorite is Trinity, for the record) and Hackers (Lord Nikon).

10. Henry Gupta - Tomorrow Never Dies (1997)

Henry Gupta at the computer

Henry Gupta, “started out as a student radical at Berkeley in the 60’s, now he sells his politics for cash.” He apparently “practically invented techno-terrorism.” Gupta’s introduction was a great reference to some of the real-life early roots of computer hacker culture, notably the University of California at Berkeley in the 1960’s, which just happens to be Steve Wozniak’s alma mater. Even better, the actor that played Gupta is the famous magician Ricky Jay. Magicians are bona-fide hackers in my book! Not only that, Ricky Jay looks quite a bit like Steve Wozniak, which also might not be a coincidence.

9. Rat - The Core (2003)

The Rat gets caught I can’t exactly remember why they needed a computer hacker to “restart the Earth’s core,” but Rat was just about the only thing I remember from this movie. Rat’s introduction was a storming of his apartment by the FBI, an event he had obviously been preparing for. His apartment was really reminiscent of Neo’s apartment in The Matrix. Dark, every surface occupied by multiple CRT monitors, and CDROMs scattered all about. Later on, he even shows off his phone phreaking skills by hacking one of the agent’s cellphones. You can check out the full scene on YouTube.

8. Luther - Mission Impossible (1996)

Luther looking cool

Famous for pulling off “The Mount Everest of Hacks”, allegedly breaking into the NATO Ghostcom. My favorite part about Luther’s scene on the train in the original Mission Impossible was his display of a common hacker character flaw–a huge ego, one that tends to get real hackers in trouble all the time.

Ethan Hunt What did they used to call you? The Net Ranger? Phineas Phreak? The only man alive who actually hacked NATO Ghostcom.

Luther There was never any physical evidence that I had anything to do with that… with that exceptional piece of work.

I love this part because it reminded me of an excellent passage from Bruce Sterling’s book, The Hacker Crackdown, where it was revealed just how much hackers love to brag about their heists:

Cops are skilled at getting people to talk, and computer people, given a chair and some sustained attention, will talk about their computers till their throats go raw. There’s a case on record of a single question– “How’d you do it?”–eliciting a forty-five-minute videotaped confession from a computer criminal who not only completely incriminated himself but drew helpful diagrams.

7. Woodstock - Ace Ventura: Pet Detective (1995)

Woodstock's lair Woodstock’s part in the very silly Ace Ventura premiere movie was really short, but impactful enough to make this list. An eccentric hippie Greenpeace hacker, his introduction was in his awesome hackerspace, located underground at a heavy metal nightclub behind an armored door. Only those with the secret password (“New England Clam Chowder”) could enter. There, he was found hacking into a whaling fleet to misdirect their GPS off course. A true white-hat! If people ask you what you’re up to on the computer, what better response than “just watching the fishes man!”

6. Brill - Enemy of the State (1998)

Brill from Enemy of the State

Enemy of the State was way ahead of its time. Produced in 1998, it centered around the plot of a corrupt politician who commanded the technical might of the National Security Agency to track down and destroy evidence of a politically motivated murder. Not only was this movie relatively technically accurate for its time (some of the bits about what satellites could do were probably a bit far-fetched), it had a wonderfully paranoid ex-NSA hacker as one of its main characters. Brill showed off a lot of great social engineering skills in the movie, and spoke with the confidence and paranoia of a true hacker. At one point in the movie, he even showed off his incredible “hacker den”, complete with equipment capable of breaking government-grade encryption and enclosed around a Faraday cage.

5. Angela Bennett The Net (1995)

Angela looking cyber hygge

The Net is one of the most technically accurate movies on this list. Angela Bennett was a professional white-hat hacker working for the megacorp Cathedral Software. Her introductory scene was a late-night hacking session reverse-engineering a copy of Wolfenstein 3D infected with a virus. In this scene, Angela was shown using several real hacking tools including a debugger, disassembler, and ResEdit for the Mac.

Besides being an extremely good hacker-for-hire, the real reason why Angela is on this list is because she lived the hacker lifestyle. After signing off from work for the day, she is shown ordering a pizza from the Internet (something only computer-y people did in the 90’s!) and cozying up next to a virtual fireplace to spend the night chatting with her cyberfriends on IRC.

A little later in the movie, Angela goes on vacation and is shown on the beach working on her laptop. A true hacker retreat.

4. Lisbeth Salander The Girl with the Dragon Tattoo (2011)

Lisbeth Salander with a Sony UX micro PC

Besides being a really deep and interesting character, Lisbeth Salander from The Girl with the Dragon Tattoo was a really great hacker. Lisbeth captured a vastly different hacker archetype than the others on this list.

While Angela Bennett languished about being alone on countless Saturday nights because of her computer addiction, Lisbeth was an actual anti-social, perhaps misunderstood grey-hat hacker. This type of hacker is not often represented in Hollywood, which is why Lisbeth is one of my top five favorites. Rooney Mara’s portrayal of this character was absolutely flawless.

Other than Rooney Mara’s superior performance as an actress, the reason why I decided to list the American remake of the Swedish film released two years earlier (which was in turn of course adapted from the novel by Stieg Larsson) was because this version had a lot of technically accurate hacking scenes, making this film probably the most accurate one on this list. Lisbeth was shown executing real SQL queries and performing spear phishing/social engineering attacks. She also dressed and behaved just like a hacker of this archetype would.

3. David Lightman WarGames (1983)

David Lightman hacking something In the introduction of this post, I mentioned that I would omit some of the obvious hacker movies. But David Lightman, the main character from WarGames is too good (and significant) to leave out of this post.

WarGames was significantly important to jumpstarting hacker culture in the 80’s. Another passage from The Hacker Crackdown:

And with the 1983 release of the hacker-thriller movie War Games, the scene exploded. It seemed that every kid in America had demanded and gotten a modem for Christmas. Most of these dabbler wannabes put their modems in the attic after a few weeks, and most of the remainder minded their P’s and Q’s and stayed well out of hot water. But some stubborn and talented diehards had this hacker kid in War Games figured for a happening dude. They simply could not rest until they had contacted the underground– or, failing that, created their own.

Who could blame them–David Lightman was indeed a happening dude. Besides beating high scores at the local arcade and hacking into the school computer to change his grades, David demonstrated another common hacker trait that I really loved in this movie: he got massively obsessed with something. My favorite scene in the movie was when David was shown intensively researching the WOPR system and its creator, Professor Falken.

In my opinion, this is what makes a truly great hacker. It’s not necessarily about skill, networking, or know-how. Instead, it’s about the drive. If you have the obsessive personality flawlessly portrayed in this movie, the ability (and time) to obtain the proper skills will follow.

This wasn’t even Matthew Broderick’s last time playing a hacker in a movie! There was an excellent scene in the 1986 classic Ferris Bueller’s Day Off where Broderick is once again hacking into the school computer to change the number of absent days reflected on his record. Okay, so maybe Ferris Bueller wasn’t as much of a hacker as David Lightman, but you gotta give it up to the great quote, “I asked for a car, and I got a computer. How’s that for being born under a bad sign?”

2. Boris Grishenko Goldeneye (1995)

Boris with his secret codes and his passwords

The last two spots on this list were really tough to judge. Boris is probably the funniest one on this list. The actor who played Boris, Alan Cumming, perfectly executed a lot of hacker idiosyncrasies. The strange sitting posture in his computer chair, a bad case of restless hands (so much so, he had developed a great skill for typing one-handed while busying his hands with a pen–later to his demise), and a classic hacker sense of humor.

I often debate with people about whether or not Boris was good or evil. Of course, he was working for the villain of the movie, but didn’t really express any personal affinity to his philosophy. Or even greed. I often think about a great quote from the villain of Hackers:

The Plague Look, there is no right and wrong. There is only fun and boring.

Some hackers are motivated by philosophy, some are motivated by status or wealth, but others are doing it just for the fun of it. Rather detrimentally to society, they don’t always care about what’s right or wrong. In some cases they’re not even capable of distinguishing for themselves.

In Boris’s introductory scene, he was caught by his friend Natalya (another great hacker) hacking into the US Department of Justice, seemingly just for a laugh. He eventually gets caught, and a trace is executed on him, at which point he shrugs it off (“besides, the Americans are slugheads!”) and proceeds to DDOS his pursuer. After succeeding in spiking them, he exclaims his unforgettable tagline (all good hackers have a tagline, right?), “I am invincible!”

1. Whistler Sneakers (1992)

Whistler disassembling something

The main cast of characters in Sneakers consists of nearly all hackers. There’s Mother, a paranoid conspiracy theorist who spent 18 months locked up for breaking into a law firm’s computer system; Carl, a nineteen year old hacker who was caught breaking into the Oakland city school district computer system to change his grades; and Irwin Emery. Also known as “Whistler”, a phone phreak born blind who “had a little problem with the phone company.”

To fans of the film, Whistler is probably most people’s favorite character. A contemplative sleuth who seems to always interject at the right time, and a perfect compliment to the skill set of the other hackers on his team. You could say Whistler’s unforgettable tagline is “don’t look, listen!”, often noticing audible details during their investigations that no one else noticed. One of my favorite scenes involved an operation where the team was casing a building, trying to draft a map of the place without physically entering the property.

Mother is aiming a super-directional microphone at different points on the building. Whistler listens carefully.

Mother Second floor, northwest three.
Whistler Uh, that’s an emergency exit.
Mother How do you know that?
Whistler I can hear the emergency floodlight batteries recharging.

Whistler was also shown using a Braille terminal to interact with his computer, which I thought was really cool.

Whistler using a Braille terminal

Although I couldn’t find any official documentation of this, Whistler was most likely based on a real hacker, Joe “Joybubbles” Engressia, one of the very first phone phreaks. Like Whistler, Joybubbles was born blind. He also possessed the gift of “perfect pitch”, which endowed him with the rare ability to whistle the infamous 2600 hertz tone into the phone line, which was a carrier signal that was often exploited by phone phreaks to make free long distance phone calls. Also like Whistler, Joybubbles was arrested for phone phreaking in 1971. I was surprised to find recently that there’s actually an upcoming documentary about Joybubbles yet to be released.

Whistler’s cool personality, heroism, truly elite hacking and social engineering skills, and historical significance is what earned him the top spot of my list. Peace on Earth and goodwill toward man!

Even though all of the characters I listed above are from movies dating back to the 90’s and early 2000’s, hackers in movies are becoming more and more common even in recent releases. They even cast Chris Hemsworth in a movie about cybercrime (can’t say I recommend it, though). Elliot Alderson from Mr. Robot is a great example of a great modern portrayal of a hacker. The creators of the show even made sure to get all the details right and hired professional hackers as consultants.

The hacker archetype is a relatively new concept in modern cinema. Heck, it’s a relatively new concept in society in general. I find it extremely entertaining whenever Hollywood gets it hilariously wrong or shockingly right.

Posted 26 March 2019