When it comes to making the most of the internet and social media to jumpstart your career, you won’t find anyone more skilled at it than the multi-talented Gaby Dunn. After graduating with a degree in multimedia journalism from Emerson College, Dunn was pretty savvy about using the internet to create her own mini-empire. Her first foray into social media was her Tumblr blog, 100 Interviews, which quickly got her noticed. She expanded into a more visual medium when she started her popular comedy YouTube channel, Just Between Us, with her best friend Allison Raskin. That channel now has over 730,000 subscribers and 150 million downloads to date.

But with all of that success, Dunn was still struggling with money issues, which led to her next endeavor. In 2016, she started producing a podcast called Bad with Money with Gaby Dunn, which analyzes common money problems that people have and never talk about. The podcast was such a hit, that Dunn wrote a Bad With Money book that drops in January of 2019. According to her, “Most financial books are for rich people. This one is for the rest of us.” With such an impressive Internet resume, what better person to pick some ‘must see’ movies about the online world?

Although Gaby has a background in comedy, her movie picks leaned heavily toward more serious takes on the subject matter. “It's funny to look back on this time period when the Internet tended to be the ‘villain’. Everyone was terrified about the possibilities. I remember when AOL first came out, and being warned constantly not to talk to strangers or give them your personal information. Now all we do is get personal on the Internet. We live online.”

But why just live online when we can also watch movies about living online? Here, exclusively for Caavo, are Gaby Dunn’s picks for must-see movies about the Internet!

The Social Network (2010)

This David Fincher masterpiece about Mark Zuckerberg is even more relevant today considering how influential Facebook has become in the last few years. Although on the surface it’s a standard biopic about the creation of the social media giant, underneath it all it’s an intense character study about the people behind it. According to Dunn, “It portrays the startup culture so well. These were just college kids messing around, and none of them understood how serious what they were doing would get. It was a perfect storm.”

Hackers (1995)

Angelina Jolie stars in this cyberpunk thriller as a member of a group of high school hackers who try and take on an evil corporation. This is one of the earliest films to explore the topic of the internet and it still holds up today. “This really sold the idea of the Internet as this cool world and this hacker lifestyle that you really wanted to be a part of. It was almost like Harry Potter for the Internet.” Catfish (2010) Before the hit MTV show, this documentary explored the phenomenon of people who create completely false personas online and the victims taken in by the lie. Dunn was blown away by the film when she first saw it. “The twist was so mind blowing at the time. It was amazing that anyone would go to that length pretending to be something they weren’t.”

You’ve Got Mail (1998)

This early digital age rom-com starring Tom Hanks and Meg Ryan, two bookstore owners who fall in love via email, has lost none of its charm twenty years later. Dunn agrees. “This movie shows the positive side of meeting someone on the Internet. Best case scenario, they are the love of your life. Unfortunately, this has happened for probably two, maybe three people in the history of the world.”

The Net (1995)

When an Internet obsessive played by Sandra Bullock gets her hands on a mysterious disk, people start dying. Is she next? Dunn credits this movie with being an early entry into the ‘Cautionary Internet Tale’ movie genre. “This movie warned us about the dangers of never interacting with people in real life, because you're always online. Clearly, no one listened to what The Net was warning us about!”

The Matrix (1999)

Even if you’ve never seen The Matrix, you’ve probably seen its stylistic influence in everything from comedy parodies, to commercials. The movie stars Keanu Reeves as a cyber criminal who learns the truth about a simulated reality called ‘The Matrix.’ This is one of Dunn’s all time favorite movies. “It took everything to the next level. This movie created this whole aesthetic that has set the standard for what everyone thinks of as ‘computer people’ now.”

Citizenfour (2014)

This Academy Award-winning documentary tells the story of whistleblower Edward Snowden, who began sending encrypted emails to director, Laura Poitras in 2013. Using the alias ‘Citizenfour,’ he gave information about illegal wiretapping by the NSA post-September 11th to Poitras. Dunn prefers it to the Oliver Stone movie based on the case. “It explained what he did in a very understandable way, while also humanizing him. It was riveting.”

Hard Candy (2005)

Ellen Page stars as a teen turning the tables on a predator she meets online in this gripping thriller. Dunn describes it as a cinematic version of NBC’s To Catch a Predator. ”The performances in this are amazing. This is the dark version of You’ve Got Mail.”

Cry Wolf (2005)

This slasher flick stars Supernatural’s Jared Padalecki as a high school student involved in an elaborate game involving a fake email and a serial killer that goes horribly wrong. I mean, how could it not? Dunn loves the movie because it’s trashy fun that plays off of real fears. “I think we all kind of have a fear that something you do online will seep into your real life. In this movie that’s exactly what happens. Only instead of being maybe embarrassed, people get killed.”

Download the Caavo TV & Movie Guides mobile app to add Gaby's selections to your own what-to-watchlist today.

By Desi Jedeikin

Photo credit: Doug Frerichs