The Onion's Custom Content Agency Makes Brands Seriously Funny

Why Brands Struggle to Be Funny

In an era where attention is the scarcest resource, brands face an impossible-sounding mandate: be entertaining, or be ignored. Yet for every viral brand moment that captures cultural lightning in a bottle, there are dozens of failed attempts at humor that land with awkward silence--or worse, generate backlash that dominates headlines for days.

The challenge isn't lack of effort. Marketing teams pour countless hours into brainstorming sessions, whiteboarding "funny" content concepts, and reviewing creative briefs. The problem is that genuine comedy requires skills most organizations simply don't possess in-house: understanding timing, cultural context, self-deprecation, and the fine line between edgy and offensive.

Most brands approach humor like a checklist item rather than a craft. They want their content to be "shareable" and "engaging" without understanding what actually makes audiences laugh. This gap between intention and execution is where professional comedic expertise becomes invaluable--something The Onion recognized over a decade ago and has built an entire agency around solving.

As the media landscape evolved and brands increasingly competed for attention in social feeds, the pressure to entertain has only intensified. Internal creative teams, already stretched thin managing multiple channels and campaigns, rarely have the luxury of honing comedic craft. The result is a sea of content that tries desperately to be funny while understanding none of the mechanics that make humor work.

This challenge has led many organizations to reconsider their content strategy entirely, recognizing that authentic voice--whether comedic or authoritative--requires intentional development rather than casual implementation.

The Onion's Entry Into Branded Content

The story begins not with a grand strategy, but with a desperate client. In 2012, Microsoft faced an impossible sell: introducing a new version of Internet Explorer to an audience that had long since abandoned the browser for Chrome, Firefox, and Safari. Negative perceptions were deeply embedded in cultural memory--IE was slow, insecure, and outdated.

Rather than fighting uphill against these perceptions with traditional marketing claims about speed and security, Microsoft's marketers did something unexpected--they leaned into them. They approached The Onion to help craft what would become "The Browser You Loved to Hate" campaign, complete with a dedicated Tumblr and parody videos that acknowledged IE's troubled history while positioning the new version as a genuine fresh start.

The campaign's success didn't just move the needle for Microsoft--it proved a thesis that would reshape The Onion's business model entirely. Here was proof that brands could use authentic, self-deprecating humor to connect with audiences in ways that traditional advertising never could.

By 2013, The Onion had formalized this capability into Onion Labs, a custom content division that brought the publication's comedic expertise to brands like Dove, MTV, EA Games, Hilton, and others. The agency worked with 15-20 brands annually, targeting 50-60 projects with a lean team of 8 core members who understood both comedy and brand objectives.

The evolution continued through 2025, when The Onion launched "America's Finest Creative Agency," a further expansion of their branded services under the leadership of Marnie Shure and Howie Kaplan. This new iteration maintains the core commitment to authentic comedy while expanding into modern formats--social-first vertical video, stunt marketing activations, and email copy that subscribers actually want to read.

What has remained consistent across this evolution is a fundamental belief: humor is a craft that requires expertise, and most brands don't have that expertise in-house. Organizations looking to understand how AI and automation intersect with human creativity should explore our guide on AI in marketing to see how these approaches complement each other.

Why AI Can't Do This

As brands look for efficiency gains and cost optimization, many have turned to AI tools for content creation. The volume of content needed to maintain social presence seems to demand automation. However, The Onion's leadership isn't worried about competition from large language models--and their reasoning reveals something fundamental about effective comedy.

The reason AI struggles with humor is not a technical limitation that will eventually be solved. It's structural. AI systems are trained to predict the most probable next token, the safest completion, the most middle-ground interpretation. Comedy works through the opposite principle: surprise, subversion, and the unexpected.

Great humor often walks a fine line. It requires judgment that comes from immersion in cultural conversations, the ability to understand when a reference will land and when it will fall flat. Self-deprecation works only when it feels genuine, which requires understanding the specific relationship between a brand and its audience. Irony requires shared context that AI cannot access or understand.

AI also cannot take the risks that great comedy requires. The best brand humor occasionally fails--and the ability to distinguish between productive failure and reputation-damaging misstep comes only from experience. As Leila Brillson, CMO of The Onion, noted, AI flattens content into the broadest, safest middle ground, which is precisely the opposite of what makes humor memorable.

This doesn't mean AI has no role in comedic content workflows. It can assist with drafts, generate variations, and help with structural organization. But the core creative judgment--the thing that makes content actually funny--remains deeply human. For brands exploring AI content tools, understanding both the capabilities and limitations is essential--see our comprehensive guide on how to use AI-generated content effectively.

Maintaining Authentic Voice

The greatest challenge for any branded content partnership is maintaining authenticity while serving brand goals. For The Onion, this means never compromising their voice--even when clients request changes that would make content "safer" or more conventionally marketing-like.

"It's all about making sure that The Onion's voice is maintained and you are trying to fit a brand where it doesn't belong, so it is challenging," explains Grant Jones, director of marketing at The Onion. This commitment to authenticity means the agency sometimes says no to potential clients, declining work that doesn't fit their comedic approach.

Not every brand is a fit for comedic content, and not every campaign idea deserves execution. The Onion's reputation depends on knowing where the line is--and helping clients find the humor that works for their specific situation rather than forcing jokes that feel unnatural. The vetting process for brand partnerships involves assessing whether the brand's identity and audience expectations align with comedic content.

The collaborative process begins with understanding both the brand's objectives and their existing voice. From there, The Onion's team identifies natural opportunities for humor rather than forcing comedy into inappropriate contexts. This might mean advising a client that their serious B2B product isn't well-suited for The Onion's style--or finding an unexpected angle that works for both parties.

Internal teams can learn from this approach. Rather than treating humor as a layer applied to existing content strategies, successful comedic branding requires alignment between voice, audience expectations, and content format. When these elements align, humor amplifies message retention and brand affinity. When they don't, even well-executed comedy falls flat.

For brands considering humorous content, the first question should never be "what should we joke about?" but rather "does our audience expect this from us?" Building comedic brand identity requires consistency and earned permission, not occasional forced levity. Organizations seeking to build cohesive AI automation strategies can apply similar principles--ensuring technology enhances rather than replaces authentic brand voice.

Lessons From Campaign Work

The Onion's decade-plus in branded content has yielded hard-won insights about when and how humor works in marketing. These lessons apply regardless of whether brands work with external comedy partners or develop internal capabilities.

Self-deprecation works when authentic. Brands that acknowledge their imperfections in genuinely clever ways earn audience trust and differentiation. The Microsoft IE campaign succeeded precisely because it didn't pretend the browser's problems didn't exist--it made them the content. However, brands that try to fake self-deprecation are called out instantly by audiences who can detect inauthenticity. The permission to joke about yourself must be earned through consistent voice and genuine character.

Distribution strategy matters as much as creative. The best content fails if it doesn't reach the right audience at the right time in the right context. The Onion's owned channels provide distribution leverage for their campaigns, but successful brand humor also requires platform-specific strategies. What works as a standalone video may need adaptation for social feeds, and the comedy that earns engagement on TikTok may not translate to LinkedIn.

Not every brand is a fit for comedy. Some brands have earned the right to be funny through consistent voice and long-term audience relationship. Others need to build that foundation first through valuable, informative content before attempting entertainment. Jumping straight to humor without established brand credibility often backfires.

Comedy is a genuine differentiator. In a sea of lookalike content that follows the same formulas and templates, genuine humor cuts through precisely because most brands can't execute it well. The brands that do comedy well stand out not because humor is novel, but because the execution quality is rare. This is why professional comedy expertise commands premium pricing--it's genuinely difficult to do well.

For marketers considering humorous content, these lessons suggest a strategic approach: build audience permission first, ensure self-deprecation feels genuine rather than forced, invest in distribution as seriously as creative, and recognize that comedy quality reflects on overall brand competence. Understanding AI idea inflation and how to balance human creativity with automation tools can further strengthen your content strategy.

Sources

1. Content Marketing Institute - The Onion's Custom Content Agency - Original coverage of Onion Labs launch and services
2. Marketing Brew - The Onion Creative Agency - Latest agency launch details and executive quotes
3. Digiday - The Onion's Quest to Make Brands Funny - Historical context and brand collaboration details