Copywriting Strategy: How to Write for a Jester Brand (And Not Look Like a Fool)
July 31, 2025
Notes on branding and copywriting in the age of AI
Do You Write for a Jester Brand?
Better Copywriting for a Jester Brand Archetype, With Ideas For Using AI
Brand archetypes can be incredibly powerful. An archetype defines and animates the way your brand looks, sounds, and behaves, both inside and outside your organization. I’ve often had push back from people who worry that selecting one of the 12 archetypes for a brand is too limiting. Yes, it limits. But powerfully focusing your communications requires ruthless cutting and sacrifice. If you’re a little of this and a little of that to everyone, no one will care about you.
Of the 12 archetypes, few are as magnetic and memorable as the Jester. While other archetypes focus on stability, transformation, or mastery, Jester brands help audiences break free from the mundane with playfulness and fun. You want consumers to say, “Hey wait, that looks kinda fun, and I want to be part of it."
How do you define a Jester brand? It’s one that relies on some combination of originality, irreverence, wit, and playfulness so that people feel joyful, spontaneous, and unbound by norms. Jester brands don't necessarily promise better products—they promise a better time, a break from convention, and an attitude that doesn’t take everything so dang seriously. In a word, entertainment.
Understanding the Jester Brand Archetype Territory
The Jester is one of the three archetypes that inspires freedom, sitting right alongside the Rebel and the Explorer. But where Rebels inspire through disruption and Explorers through independence, Jester brands inspire freedom through laughter and play. Essentially, Jesters say, “let’s not take this all too seriously.”
Their core motivation is entertainment, finding ways to spark joy that breaks down barriers and creates connection through shared fun.
A Jester Brand Sells Underwear
We’ve Written Copy for Numerous Jester Brands. Here’s One Example.
Here’s an example of a Jester Brand. I developed and wrote the “Overachievies” campaign for AYG Underwear. The ads and marketing tactics were a sassy, irreverent Jester rather than a darkly funny or gently winking Jester in the examples below. The AYG campaign included print ads, an Outdoor Retailer tradeshow booth, t-shirts (“while you’re obsessing about gear, don’t neglect your butt”), and an “Underwear Cam” mobile app that superimposed AYG underwear on photos and posted them to a website.
One of the ads in the Overachievies campaign
Jester Brand Voice Examples: Getting into Its DNA
Successful communication from a Jester brand relies on several key principles that distinguish it from other archetypes.
1. The Language of Play
Jester brands don't just serve or deliver. They try to delight, surprise, celebrate, and bring levity. Every piece of content should feel like it's entertaining people, inviting them into a more playful reality.
2. The Promise of Unexpected Joy
While Leader brands promise control and Sage brands promise understanding, Jesters promise delight even in mundane experiences. This means finding humor in places and at moments where competitors take themselves too seriously.
Wide Range of Jester Brand Examples
Jester Archetype in Consumer Brands: Ben & Jerry’s, Old Spice, Dollar Shave Club
Back to my point about focusing: Choosing a single archetype is less restrictive than you’d imagine. Jester brands, for instance, can have a range of expression. While Ben & Jerry’s expresses itself as playful, lighthearted, and slightly irreverent, Old Spice trades in absurdist humor, reminding us not to take ourselves too seriously when we’re applying deodorant. Dollar Shave Club, meanwhile, shoots for a disruptive slapstick in their communications. Liquid Death uses more in your face humor and a push-the-limits irreverence, a long ways from the softer Ben & Jerry’s Jester expression.
Jester Archetype in Insurance Brands: Geico, Progressive, State Farm, Allstate
The insurance industry, interestingly, is full of Jester and wannabe Jester brands. Geico started the industry’s branding fad with advertising that’s randomly and consistently hilarious. Often their jokes have a tenuous relevance to insurance, but the way they advertise is pure entertainment, giving them a powerful word-of-mouth advantage.
Progressive, State Farm, and Liberty have all tried to entertain with jokes and absurd humor, but none of them are as consistently funny as Geico. Progressive and State Farm are more “dad joke” Jesters, and, personally, I have to change the channel when Liberty’s emu shows up—those spots are just irritating. At least Progressive and State Farm offer some relevance in their ad work.
The big warning here is that managing and writing for Jester brands can be fraught. The humor and entertainment are in the eye of the beholder and need to land with your target audience. Getting humor to work can be hard.
AllState, yet another insurance Jester brand, executes the archetype best. Their “Mayhem” campaign is consistently funny and totally relevant to the product they’re selling.
Content Strategies for Jester Brands
Headlines That Disarm with Humor
Transform functional headlines into conversation starters that make people smile before they even know what you're selling.
Instead of: "5 Ways to Improve Customer Service" Try: "Customer Service So Good, You'll Look Forward to The Hold Music"
Instead of: "New Product Features Available" Try: “Someone Dared Us to Build This New Feature"
Instead of: "How to Increase Team Productivity" Try: "Productivity Hacks That Don't Involve Drinking More Coffee (But You Still Can)"
Storytelling That Celebrates the Absurd
Structure your content around moments of delightful surprise. Share customer stories that focus less on use-case outcomes and more on the unexpected joy of the experience. Highlight the moments where your brand made someone laugh, smile, or feel lighter.
Content as Entertainment
Position your expertise not as a lecture, but as a crack-up. Frame your content as fun insights, entertaining observations, or playful experiments that happen to be useful.
Consider Infusing Jester into Testimonials
Collect and showcase testimonials that emphasize the emotional experience of working with you. Look for language like "They made shopping for a car fun, like I should do it more often.”
How to Prompt AI Tools to Get the Best Content for Your Jester Brand
When working with AI to generate content for Jester brands, your prompts need to embed the right sort of playfulness while maintaining authenticity. Make sure to use the right nuances for your particular brand. Ben & Jerry’s, for instance, wouldn’t use prompts like “irreverent,” “absurdist,” or “dark comedy.”
For Brand Archetype Copywriting, Always Set the Context
Always begin by establishing your brand archetype with focused context:
"You're writing for a Jester brand archetype. Our version of this archetype relies on [your particular Jester nuances] so that people feel joyful, spontaneous, and unbound by norms. The Jester’s motivation is entertainment, making ordinary experiences unexpectedly delightful.”
Entertainment-Focused Prompts
Write your requests as invitations to play.
"Write a blog post that takes readers from [boring industry convention] to [surprisingly fun perspective]. Position our [product/service] as the refreshing alternative that doesn't take itself too seriously. Use humor that's clever but accessible, and include unexpected analogies or observations."
Language Guidelines for AI
Create a vocabulary library that captures your brand’s particular playful spirit.
As I mentioned, humor can be hard, so you may have to push your AI tool beyond corny groaners.
Define your brand’s version of Jester.
Advanced AI Copywriting Prompts for Jester Brands
The Unexpected Twist Prompt
"Using the Jester brand archetype, write [content type] that follows this structure: 1) Start with a common, slightly boring assumption about [topic], 2) Introduce an unexpected but true perspective that reframes everything, 3) Show how our approach makes the whole experience more enjoyable, 4) End with an invitation that feels more like joining a fun community than buying a product."
The Comic Relief Prompt
"Find the absurd, amusing, or unnecessarily complicated aspects of [industry/topic] and offer our brand as the refreshingly straightforward (and fun) alternative."
The Playground Prompt
"Write as if you're inviting people into a space where the usual rules don't apply—where [serious topic] can actually be enjoyable. Use the Jester archetype's emphasis on originality and playfulness to make complex ideas accessible and entertaining.”
The Advantage of Jester Brands
In a world where most B2B and even B2C communication feels like it was written by robots for robots, Jester brands have a advantage: they give people permission to enjoy themselves. When optimized correctly, Jester brand content doesn't just inform or persuade—it creates positive associations by way of entertainment.
Example Product Copy For a Jester Brand
Here’s the prompt I used in Claude Sonnet 4: "Rewrite this product in the voice of a Jester brand."
BEFORE
Our Men's Boxer takes all the tech you love from our boxer briefs—lightweight, breathable, anti-odor—and adds a looser fit. With a fully functional fly and a wide, elastic waistband, you'll experience maximum comfort all day. No matter if you're hitting the trail for a three-day camping trip or just want all-day comfort everyday, our Men's Boxer brings you all the performance and comfort you want.
AFTER
Our Men's Boxers are in on every underwear joke. They pack all our greatest hits—lightweight, breathable, anti-odor—into a gloriously loose fit (because nobody likes a clingy friend). The fully functional fly and wide, elastic waistband work harder than they have to, like they’re always on deadline. Perfect for wearing three days straight on camping trips or on regular Tuesdays when you want to feel like you've got your shit together—at least from the waist down.
Brand Voice Copywriting Beyond Brand Archetypes
As you can see, simply identifying a brand archetype for an AI tool made the copy much more engaging and memorable. When you add purpose, attributes, values, and other foundational brand elements, the transformation becomes even more dramatic. The key is consistency—every piece of content should reinforce your brand's unique way of seeing and communicating about the world. If you write from a Jester brand, live it everyday.
