Funny Copywriting: How to Write with Humor and Still Make a Point

My therapist told me I use humor to deflect. I told her I use it to create engaging content people actually read. We’re still working through it, but in the meantime, welcome to my masterclass on funny copywriting.

The goal here is to build a brand voice that’s half cheeky uncle, half surprisingly effective mentor. You’re the one who shows up with bad puns and, somehow, brilliant advice. We’re aiming for a personality that can make a blog post about tax law feel like a stand-up special—with highly applicable homework, of course.

A friendly, approachable mentor who is also cheeky and funny, embodying the 'cheeky uncle' and 'effective mentor' persona.

The Art of the Chuckle: Your Comedy Toolkit

Alright, let’s get down to it. Here’s how you actually pull off humor in copywriting without sounding like a dad desperately trying to use TikTok slang.

Your Hook Needs a Hook

Start with a painfully good pun or a weird story about your cat. Your first sentence is a handshake. Make it firm, a little weird, but definitely memorable. This is your first chance to create relatable content.

Embrace Self-Deprecation

Let’s be real, you’re writing about software updates, not the final season of Succession. Acknowledge the topic might be dry. “I know, corporate budgeting isn’t a thrill a minute, but stick with me. It gets spicy. I promise.” (It probably doesn’t, but confidence is key).

Invent Conversations

“My 7-year-old just asked if a ‘balance sheet’ is something you use at the playground. Honestly, it’s a better question than most I get.” Talking to your inner monologue or a hypothetical reader makes you instantly more relatable. You feel me?

Be Radically Conversational

Use phrases like “Hot take incoming…” or “cue dramatic eye roll.” Ask rhetorical questions. “Still here? Wow, you must really like me.” Breaking that fourth wall makes the reader feel like they’re in on the joke.

Master the Tone Shift

The magic trick is knowing when to shift gears. You can drop a terrible dad joke and follow it up with a genuinely profound insight. That whiplash is a core part of effective, funny copywriting.

End with a Zinger

Finally, end each section with a clever takeaway or a classic “and yes, this will be on the test.” It’s the prize at the bottom of the cereal box.

A 'copywriting toolkit' for humor, showing quirky items like a fish hook for a strong opening, a winking emoji, and speech bubbles.

From Drab to Fab: A Copy Makeover

“Okay,” you say, staring blankly at your screen. “Show me.” Fair enough. Let’s do a quick makeover.

A before and after scene of a person reading a report; they go from bored and disengaged to laughing and interested.

When you have to talk about numbers:

“Now, before your eyes glaze over like a fresh Krispy Kreme, let’s break down this quarterly report…”

You’ve acknowledged their pain. You’re a hero.

When you have to drop a boring-but-important fact:

“Alright, here’s the ‘eat your vegetables’ part of the article. This is actually fascinating. Or maybe I’ve stared at this topic for too long and my definition of ‘fascinating’ is broken.”

An audience that is both laughing and learning, illustrating the 'Entertain First, Educate Second' philosophy.

Your Mission: Entertain First, Educate Second

So, what’s your mission? Entertain first, then educate.

If your reader feels like they got career advice from their favorite weird uncle—the one who wears Hawaiian shirts in winter but knows the secret to a perfect IPO strategy—you’ve done it.

They should laugh once, learn something twice, and maybe wonder if you’re okay. Hit all three? That’s how you create engaging content that builds a loyal audience.