“When the going gets weird, the weird turn pro,” said Hunter Thompson in 1972. His point, that during periods of societal uncertainty – periods of “weirdness” – the weird are poised to lead and people are poised to follow, might equally apply to today. Whether the chorus of singing toilets in Liquid I.V.’s ad or the deliberately stilted comedy of the Skittles stunt broadcast live from an unsuspecting customer’s doorstep, even brands advertising to the mass audience of the Super Bowl seem to be recognising the value of weirdness.
Among other things, they’re recognising that weirdness speaks to consumers’ present cultural moment – one of strange technology, strange presidents, and strange weather – far better than the cautiousness of another campaign that plays it safe. This follows years of the exact opposite. Social media exposed brands to audiences in a new way, opening a direct dialogue between the two. With visibility came judgment and, scared of backlash, droves of brands opted for blander approaches. This fear, compounded by cancel culture and boycotts, manifested attitudinally, in communications, but also aesthetically, in generic logos, websites, and fonts – all minimalist, all undifferentiated. This homogenisation was data-driven, in part, as its spread beyond brands – to architecture, literature, illustration, and even furniture – attests; when an attempt to engage an audience is based on aggregated data, rather than a personal creative vision, it relies on statistical averages, predictable patterns, and, ultimately, mimicry, hence the sameness. Often, these “appeal” to everyone, while connecting with no one.
Sameness predates AI and algorithmic cultural flattening but both have also dramatically exacerbated it – and now, to stand out, more and more brands are embracing weirdness instead. In opposition to the machines, they’re embracing friction, personality, and the element of surprise. So, how’s that going?
The weird and the wonderful.
According to HubSpot, 86% of shoppers prefer brands to show a more authentic and honest personality on social media. Weirdness is authentic – it’s often unfiltered, unpolished, human, and relatable – but it goes further than authenticity alone. Indeed, rather than human and relatable, weirdness can equally manifest in the uncanniness of the inhuman (of the synthetic or supernatural or machine-like) and the dissonance of the unrelatable. That grabs attention. And it’s likely on that basis that today’s weirdness most appeals: as unexpected, it stands out. ‘Authenticity’ is almost a cliche for brands, at this point – true weirdness isn’t.
Today, the most obvious forms of weirdness manifest culturally, in the rise of weird fashion trends, weird hobbies, and weird subcultures, all of which signal distinctiveness for the participants while simultaneously offering – because of the loyal communities and cult followings orbiting each – a sense of belonging. But for brands the form it takes most often might be humour, particularly of the cringe variety. Humour offers brands a safe(ish) way to be weird, which is probably part of its appeal: if things go awry, a brand can always retreat to the position that they were “only joking”.
According to Kantar, the proportion of ads that use humour has dropped from 53% in 2000 to 34% today, even though Oracle recently found that 90% are more likely to remember a funny ad and 80% are more likely to buy from a funny brand. That gap offers an opportunity to stand out to consumers, for brands brave enough to buck trends and be funny or even a little unhinged. Wendy’s might’ve pioneered the approach but low-cost airline Ryanair, for example, also routinely mocks itself, with an even lower-cost social strategy, marked by AI-generated voiceovers, glitchy edits, deliberately pixelated filters, and self-deprecating commentary on their many customer complaints. It succeeds because, unlike slicker brands, Ryanair demonstrates a personality. And any consumers repelled by the “wrongness” of that personality aren’t, arguably, very likely to buy from the brand in the first place, thus concentrating their true believers and, consequently, forging that loyal, cult following for the brand, with that attendant sense of belonging.

Plenty of other examples of brand weirdness are, well, far weirder. Duolingo, for instance, “killed” its beloved owl mascot Duo. Users opened the app one morning last year to find Duo murdered, with his tongue out, eyes replaced with Xs. Mournful posts on social media followed, featuring a video of Duo run down by a Tesla Cybertruck and a funeral attended by other mascots, all also later killed, with users encouraged to “bring Duo back” by completing more language lessons. Subsequently, mentions of Duo spiked by around 26,000%, the hashtag “#RIPDuo” was used 45,000 times, 450 articles were published on the campaign, downloads of Duolingo increased by 38% on Android, and web searches by 58%.

For other brands, weirdness is more whimsical and surreal. Sportswear brand On recently released a highly abstract ad to promote its collection co-created with Zendaya. Directed by Spike Jonze (of Being John Malkovich and Her fame), the ad is set inside a “dream lab”, focusing less on product features and more on the creativity and imagination behind it. A hit with viewers, ads like this capture attention amid heaps of more faceless fare not because they exhibit “personality” but because they exhibit a personality – a specific personality, in this case Spike Jonze’s. It’s the difference between a carefully managed committee of twenty marketers trying to feel human and a brand simply being human, by entrusting its campaign to someone specific with a unique vision, which only they could’ve realised. Similarly, Wendy’s social media content didn’t go viral because of a focus group; it went viral because audiences recognised in its voice the single personality of someone trusted by a superior to speak like they actually speak, without compromising. The appeal of influencers hinges on a similar principle: people want to speak to people and each influencer is a specific person, not a brand.
The weird and the wary.
Misfits, outsiders, eccentrics, geeks: all evidently have a value, which often goes untapped. However, that value has a ceiling. Most of the aforementioned examples of brands embracing weirdness aren’t mass-appeal, relative to their respective industries’ biggest players, and the bigger the brand the more mass-appeal and the more risk-averse it (usually) needs to be. Weirdness works well for a language app but it’s unlikely that audiences would want, for example, their bank to behave as strangely. Context plays a role too: a brand advertising funeralcare probably wouldn’t suit an “unhinged” approach either. That said, at first glance the same might’ve been said about an airline or a political party – The Simpsons made jokes about both the former and the latter – and look at Ryanair and Donald Trump.
The question a brand needs to ask itself, then, is, “Can we afford to be weird? And if so, how weird?” The answer to that depends on several factors, the most important of which we can map across two axes, plotting a brand’s market position (i.e. whether it’s an incumbent or challenger brand, mass or niche) and how high the stakes are for customers in the brand’s industry (i.e. how significant it is to earn their trust and for the product to be perceived as safe and reliable). This creates four quadrants; a brand’s position within those dictates the degree of imperfection, friction, and outright strangeness it can leverage securely.

Unhinged cult building
This is the quadrant that grants the most freedom for weirdness – and perhaps rewards it the most, too. When acquiring customers relies on cutting through a lot of noise and the product itself isn’t responsible for a great deal – when its failure or success poses little risk to the customer – brands have less to lose (and everything to gain) by filtering for true believers.
This is the quadrant in which the Duolingo owl gets murdered. A language app poses almost no risk to its user, so it can trade corporate consistency for chaotic unpredictability. The fact that this is also the quadrant that an airline has chosen to operate in is even more fascinating. By passenger numbers, Ryanair is Europe’s largest airline. But despite its structural status as an incumbent brand, it acts culturally as a challenger, disrupting the norms of its industry’s safe, reliable messaging, with janky social edits and by erratically ridiculing customer complaints – a rejection of the typical incumbent playbook. That highly unexpected corporate posture makes the brand’s behaviour feel distinctively, brilliantly weird.
Surrealist revamp
When an established brand in a low-stakes industry faces algorithmic invisibility or category fatigue, its behaviour doesn’t necessarily need to go as far as “unhinged” to gain attention. Instead, it can adopt a more subtly avant-garde approach to refresh its image, without the risk of alienating its existing customers.
This is the quadrant in which On’s collaboration with Zendaya belongs. As a major player in sportswear, On doesn’t need to resort to shock value: a whimsical, surrealist vision more than suffices to assert some personality and stand out in a crowded market.
Subversive transparency
In high-stakes sectors like finance, healthcare, or insurance, trust is paramount. And for legacy incumbents, trust tends to be built through a façade of faultlessness and infallibility. Challengers entering these sectors anew, though, do need to differentiate themselves, within the parameters set by that critical need for trust. For them, “weirdness” manifests more subtly than it does in other quadrants, often as radical, almost jarring transparency, which can expose the stuffiness of the category.
This is the home of modern healthcare or fintech challengers (think: Hims or Monzo). They use unconventional, informal, and unfiltered tones of voice to demystify complex systems, showing that sometimes the fastest route to trust is being “real” rather than corporate.
Calculated humanisation
Failure isn’t an option for market leaders in high-stakes industries – nor is the liability of truly unhinged weirdness. If extreme weirdness appears out of nowhere after, say, decades of straight-laced branding, it risks reading almost like a psychotic break, which too few customers will tolerate from their bank or health insurer. Still, these brands can mitigate the effects of algorithmic flattening by strategically – selectively – embracing human imperfection: a diluted form of weirdness, at least in such a polished context.
They can take cues from Patagonia, which openly shares its slips on the path to true sustainability with a message that says, “We’re not there yet, but we’re trying” – a message that regularly earns the brand the top spot on the Axios and Harris rankings of major brand reputations. Similarly, Ben & Jerry’s owns its many failed flavours with the Flavour Graveyard, writing about them with self-deprecating charm.
In a world of increasing homogenisation, the brands that dare to be weird are the brands that stand out. Ultimately, the trick is to know how weird to be.