Humor in the Age of AI: You Can’t Automate a Benign Violation
AI is adept at writing emails, polishing professional replies, and conducting broad research on complex topics. However, there remains one area where it consistently falls short: humor. Jokes. AI simply has no real edge when it comes to making people laugh.
Humor does not have predictability. It lives in disruption.
It bends rules without breaking them. Humor thrives on specificity rather than scale. It depends on timing, cultural nuance, shared context, and, often, a willingness to risk falling flat. In other words, humor resists formulas.
For Paddy Gilmore, humor is not merely a stylistic choice; it is a distinctly human advantage, one rooted in insight, judgment, and psychology.
In a marketing landscape increasingly shaped by predictive models and generalities, that human edge may prove more valuable than ever.
Why Paddy Gilmore believes it remains a human advantage
AI can scan decades of data in seconds and replicate patterns that once took humans years to master.
But can it make you laugh?
For Paddy Gilmore, founder of Humourscope and author of Amusing Comms, Amazing Growth, the answer is clear: not really.
In a marketing landscape increasingly shaped by predictive models and optimization, Gilmore argues that humor remains one of the last defensible human advantages.
Humor as “benign violation”
When asked how he defines humor today, Gilmore doesn’t see it as something modern or evolving. Instead, he sees continuity.
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“Humor today is very similar to what it was 1,000, 2,000, or even 3,000 years ago,” he says. “At its core, humor is a form of social play. It’s an acceptable kind of social violation.”
He draws on the psychological concept of “benign violation”, the idea that humour works when something feels wrong, but safe.
“If you commit a real social violation, like driving your car on the pavement, that’s dangerous and unacceptable. But humor bends reality. It disrupts expectations. It challenges norms, in a safe frame.”
That frame is everything. Everyone understands the context is playful. That shared understanding creates freedom to shift perspectives, question assumptions, and challenge ideas without triggering defensiveness.
In marketing terms, that’s a powerful territory.
Can AI ever be funny?
In an era where tools like OpenAI’s ChatGPT can polish language instantly, the natural question follows: where does humor fit?
Gilmore is blunt.
“Fundamentally, I don’t think AI can properly integrate with humor, at least not at the moment,” he says. “Humor and human are very similar words, and that’s not accidental. Humor is deeply human.”
He has experimented with AI tools out of curiosity, testing how they interpret jokes and comic framing. His conclusion? Limited.
AI systems are predictive by design. They generate outputs based on patterns from the past, what has been said before, and what has already been widely recognized as funny.
“But humor isn’t about generalities,” Gilmore explains. “It’s about insight. It’s about specificity. It’s about seeing something in a way nobody else has.”
When communication becomes pattern-based, it risks becoming safe. And when humour becomes safe, it loses its edge.
The role of a website
The conversation then shifts to branding and digital presence, specifically the role of a website in modern marketing.
Gilmore’s answer begins not with strategy, but with childhood memories.
Growing up in southwest England, there was a local egg seller known simply as “the Chicken Man.” He wore a hat shaped like a chicken. That was his brand. Everyone knew him from it.
He didn’t need a website. His brand was his hat.
The point is simple: marketing tools only matter if they matter to your audience.
For Gilmore’s own business, HumorScope, a website plays a central role. It functions as a hub, hosting e-books, interviews, articles, and frameworks that allow potential clients to understand their thinking.
But fundamentally, he insists that no channel is inherently important. Relevance to the customer determines value.
Can humor work in serious industries?
Humor in business often triggers hesitation. Is it appropriate? Is it risky? Does it undermine authority?
Gilmore believes context is everything.
Historically, high-risk, high-consideration categories; infrastructure, finance, large-scale B2B contracts—have avoided humour. If you’re selling a multi-million-pound hydroelectric dam, jokes aren’t the obvious route.
But that rigidity is loosening.
High-fashion brands selling £5,000 dresses have successfully incorporated humor into campaigns. The assumption that humor belongs only to chocolate bars and low-price consumer goods no longer holds.
“There isn’t a universal rule,” he says. “It comes down to how well humour fits the brand’s identity, proposition, and audience expectations.”
Humor isn’t about being frivolous. It’s about strategic alignment.
The ageism problem in advertising
Beyond AI, Gilmore points to another structural issue shaping the industry: ageism.
Agencies often hire two 23-year-olds instead of one professional in their 40s. On paper, it appears efficient. Two salaries. More output.
But something intangible gets lost.
You lose seniority. You lose judgment. You lose seasoned decision-making.
Experience, he argues, brings restraint and pattern recognition. It prevents overreaction. It sharpens instinct.
Gilmore now runs his own business and enjoys autonomy. But he acknowledges the industry-wide imbalance. For a sector built on cultural intelligence, sidelining experience is a strategic contradiction.
Amusing comms, amazing growth
Gilmore’s latest book, Amusing Comms, Amazing Growth, distils his framework into practical guidance.
The book outlines “three-and-a-half” methods to help brands stand out using humour strategically rather than randomly.
It’s also the foundation of his corporate training. When he works with brands — whether it’s Harley-Davidson or HSBC, the application differs dramatically.
Humor for a rebellious motorcycle brand will look very different from humor in global banking.
The objective isn’t to make brands funny for the sake of it. It’s to make humor commercially effective.
The human edge
As AI continues to refine communication, automate processes, and standardize tone, humor may become one of the few remaining spaces where imperfection is an asset.
Humor demands context, risk, and judgment.
In a world increasingly shaped by prediction, that unpredictability may be marketing’s most valuable currency.
