Conan O’Brien Deadpans Deepfakes
“Fantastic training for you tonight.” Sorry for manipulating one of your catchphrases, Conan O’Brien, but when you lend your talents to cybersecurity training, what do you expect?
If you haven’t already heard, O’Brien has a new hosting gig.
Celebrities are often targets for deepfakes, so it’s in their interest that humans learn to recognize them for what they are. And we all know that organizations struggle to train their employees—some will likely always fail to recognize a bad actor’s ploy to lure them in but others lose interest during “mandatory training” and zone out or simply check a box for HR and move on without retaining what they’ve learned.
So, it’s a little brilliant that Adaptive Security has tapped comedian and late-night host O’Brien to produce a cybersecurity training series consisting of 15 videos to raise awareness of deepfake impersonation and hyper-targeted phishing.
But training can be tedious.
“We wanted to build something personal and engaging, something employees would actually look forward to,” Adaptive CEO Brian Long said in a press release.
For his part, O’Brien said, “I teamed up with Adaptive Security just to figure out what these kids are up to. Turns out it’s pretty cool.”
The videos start off with O’Brien doing what he does best—a short bit, but this time framing a cybersecurity issue, followed by Adaptive’s instructional material.
It’s about time—AI-driven fraud losses are likely to reach $40 billion by 2027, according to research from Deloitte.
Calling the use of generative AI to create deepfake audio, imagery, and video “an increasing concern,” Margaret Cunningham, vice president of security and AI strategy and field CISO at Darktrace, says, “While media manipulation isn’t new, AI has dramatically lowered the barrier to entry and accelerated both the speed and realism of production.”
That means that bad actors without significant time and technical skill “can now be done quickly, cheaply, and at scale—making these tactics accessible to a far wider range of threat actors,” she says.
That points to a shifting threat landscape where “trust signals like names, voices, and platforms have become part of the attack surface,” says Cunningham.
Noting that as AI tools become more powerful and accessible, attackers will continue testing these weak points,” Cunningham says, “We can’t expect people to be the last line of defense.”
She calls for security strategies to evolve” to reflect how decisions are made in the real world, and technology must be at the center of defending against these threats, especially to keep pace with a problem that is moving at machine speed.”
Her colleague Nicole Carignan, senior vice president, security and AI strategy, at Darktrace, notes that “since the sophistication of deepfakes is getting harder to detect, it is imperative to turn to AI-augmented tools for detection as people alone cannot be the last line of defense.”
“To combat emerging challenges from AI-driven attacks, organizations must leverage AI-powered tools that can provide granular real-time environment visibility and alerting to augment security teams,” she says. “Where appropriate, organizations should get ahead of new threats by integrating machine-driven responses to accelerate security team response.”
That way, she says, “the adoption of AI technologies—such as solutions with anomaly-based detection capabilities that can detect and respond to never-before-seen threats—can be instrumental in keeping organizations secure.”
Adaptive is hoping the Conan O’Brien-fueled training videos will help users avoid being scammed by deepfakes and other AI-driven techniques, noting that “the training has always been there. The new part is that people will actually finish it.”
As Conan famously said, “I like the idea of anybody tuning in right now.”

