My ex-wife would say, “Well, maybe you shouldn’t…”
Here’s the short version: Yes, you definitely should (as long as they’re funny).
Here’s the longer version:
Clients hate jokes.
They’ve spent hundreds, thousands of hours building this product/service, years of their lives in 10-to-14-hour blocks. They skipped gradeschool piano recitals and friends’ birthday parties. They woke up in the middle of the night dreaming about this product/service. They shouted at colleagues across conference room tables. Much, much more than filthy lucre is on the line. People who create a product/service need to feel the result was worth all the sacrifice that went into it.
It’s like this:

Most human beings think making a joke means you aren’t taking the subject seriously.
Which is unacceptable. More than that, it’s an attack on all that incredibly hard work, let alone their egos.
This is the main reason most small and medium businesses absolutely reject humor in all official communications. The founder/president/CEO, whatever title the HiPPO gave herself, needs to think “THIS HAS TO BE REAL!” just like furrows-of-worry above.

Now we’ve got that out of the way — well, we still have a problem. Several problems.
The problems with humor
Here’s why (some, sad, limited) people don’t like jokes:
- Humor is subversive. The words you say aren’t exactly what you mean.
- Humor excludes because not everybody gets the joke — and those who don’t? They feel annoyed, left out, condescended to, and other bad things. (Like my friend Art said about my best-ever email, “I don’t get it. What, is this supposed to be funny? You just trying to prove how smart you are? What the hell is a Carrington event?”)
- Humor isn’t clear like business communications should be (with the exception of EULAs, NDAs, non-competes — well, virtually all legal forms).
- Humor pokes fun at someone — there’s a target of the joke. People who don’t like jokes always assume they’re the target.
- Finally, most damning of all, jokes aren’t (perceived as) serious. A particularly American sentiment. Also, this is why most people don’t tell jokes at funerals, which is a shame, because if there’s anyplace on earth you need to laugh it’s at a funeral.
My imaginary reader at this point:
“Well crap, George,” you mutter, “you’ve talked me out of it. I’ll never copywrite another joke again.” <sigh>
Wait we’re not done yet! Now that we know why haters hate, I’ll show you all the reasons you should write jokes anyway!
A priest, a copywriter, and a hippo walk into a bar…
Here are the reasons you should write jokes despite the reasons listed above.
People who get it are on the inside
Good marketing zeroes in on your target demographic and speaks to them in their own language. If your target demo takes something seriously and you make a joke about it, that’s just tasteless.
Aside: Reminds me of the time a friend of mine saw a bunch of our acquaintances sitting around a table at the Irish pub and went over to join them. He ordered a drink and said, “Jesus, you people are glum. Who died?” Turns out it was in fact a wake…
Good marketing is specific and focused on your target demo’s pain points. Good jokes are specific and focused on the ridiculous, the unexpected, and the ironic. Tell your target demo a joke and you identify yourself as one of them. “See? We think the same things are funny.”
People who don’t get it? Well, they’re on the outside — they aren’t like us.
Now, imaginary reader, you’re thinking:
“Jesus, George, what if I’m writing about a product/brand that has universal appeal? I don’t want to exclude anybody!
Good point! I rebut:
- There’s no such thing as universal appeal
- On a consulting gig, if I ask you “What’s your target demo?” and you say “Everybody,” before I even start laughing I’m going to quintuple my fee because you have no idea what you’re talking about

And another thing: you don’t tell everyone the same joke! Consider your audience — do you tell your partner, your mom, and your work buddies the same jokes? If you do, stop.
Like all your marketing, your jokes have to be tailored to your target demo. Else you’re an asshole smarting off at a wake you weren’t even invited to.
People remember things that make them laugh
Make somebody laugh and you’ll be remembered. Whatever funny thing you said? It’ll get repeated.
Even when people don’t buy what you’re selling, they’ll remember the laugh.
You don’t tell jokes to strangers
(unless you’re a stand-up comedian, or just a weirdo like me)
Most of the time in human interactions, jokes are reserved for insiders — acquaintances at the very least. Telling a joke is socially risky (for all the reasons the HiPPOs hate them, listed above). By taking a risk and trying to be funny, you’re telling your audience you trust them.
And that’s the way a great brand wants to make their customers feel.