• Write hilarious on-brand 404 pages without racking your brain for ideas
  • For conversion copywriters, marketers, web designers
  • Get a 404-page headline, subhead and CTA from ChatGPT 4 in only 5–10 minutes

Trying to write a 404 page?

A 404 page is an often missed opportunity to make your website visitor laugh. The problem is, funny copy doesn’t come easily to many of us. But you can ask ChatGPT 4 to bring the funnybone and help you write 404 pages that delight and convert.

Here’s what to do: Prompt ChatGPT 4 to write a 404 page, complete with headline, body copy and CTA. This is what ChatGPT 4 helped me create for a men’s underwear brand when I used the prompts I’m about to teach you.

Concept of 404 page for a brand called "Manmade," a men's underwear brand. Copy reads:
"Well, this is almost as uncomfortable as a wedgie. Looks like you've ventured into the underwear drawer of the internet. RETURN TO COMFORT."

Here’s how to use ChatGPT 4 to get similar results for your business or client.

Step 1: Find the brand’s origin story and snippets of copy showcasing their brand voice

The best 404 pages are those where the company makes fun of itself. Which means you need to be ready to seed some brand data into ChatGPT.

You’ll need:

  • Basic information about the company and product or service
  • A brand origin story, up to several paragraphs
  • A handful of lines of live copy (e.g., headlines, slogans, tagline)

Good places to find brand origin stories or information about the company are About pages, Why Us pages, Our Difference, and similar. Companies looove to talk about themselves, so you shouldn’t have too much trouble finding their story. You may also want to check their LinkedIn company page.

As for brand voice, be ready to paste a few snippets of copy that showcase the brand’s more expressive side. Consider borrowing copy from their social media accounts if their website is on the bland side.

Step 2: Start with this copywriting prompt

Now that you’ve gathered some brand information, you’re ready to put your trusty bot to work.

Start a new ChatGPT 4 thread, and copy-paste the following prompt:

Screenshot of ChatGPT-4 displaying the prompt for generating copy for a website's 404 page.

Copy-paste this prompt:

You are a conversion copywriter. Your job is to write an amazing 404 page for a website. The 404 page should be funny. Use a self-deprecating, deadpan tone of voice like standup comedian Jim Gaffigan. Use simple, direct language and address the visitor as "you." 

Craft copy for three parts: the headline, body copy, and CTA. Keep the body copy to 3 lines, and make the CTA suitable for a button or link. 

Make the 404 page copy fit the brand and product descriptions I'm about to give you. Do not provide the copy until I describe the brand in the next prompt.

After you hit Enter, ChatGPT will confirm it has understood your instructions with a response like this:

Screenshot of ChatGPT confirming it has understood the 404-page copywriting prompt.

Now you’re ready to give ChatGPT information about the brand and their product or service.

Step 3: Enter the brand information with this prompt

Copy-paste the following prompt, then insert information that’s specific to the brand you’re writing for.

For my first example, I chose Manmade, a Canadian brand that makes comfortable boxer-briefs using modal fabric. I copied content straight from their website into the chat:

Screenshot of prompt in ChatGPT describing the men's underwear company called "Manmade"

Copy-paste this prompt:

The brand is called [name]. They make [describe product or service]. 

Here is their brand origin story: "[in quotation marks, insert content from About page or other collateral]" 

Here is a sample of their brand voice: "[in quotation marks, insert lines of marketing copy]"

In case you’re wondering about maximum prompt length: The word on the (cyber)street is ChatGPT 4 can handle prompts of up to 4,096 characters. Which is great, because as you can see in my screenshot above, I was able to feed it quite a lot of brand info in one shot.

Take a look at what ChatGPT returned. Not bad!

But as with most things ChatGPT generates, it needs a lil’ reworkin’. But now that you’ve got a solid idea, the rest is a piece of cake. You’ll notice I tweaked a few things and moved some of the copy around:

404 Page concept for Manmade. 
Headline: Well, this is almost as uncomfortable as a wedgie.
Subhead: Looks like you've ventured into the underwear drawer of the internet.
CTA: Return to comfort
Not their actual 404 page. I used Chrome’s “Edit Anything” extension to change the display in my browser.

Step 4: Tell ChatGPT to generate better copy, as needed (to write a 404 page that’s fantastic!)

Sometimes ChatGPT 4 gives me a great first result. Other times, it’s meh. If you find there’s not much to work with, decide what you don’t like about it and prompt some more.

Depending on what brand information you provide, your results will vary.

For example, in one experiment ChatGPT gave me much wordier, bloated sentences. And they weren’t funny enough. So I prompted it like this:

ChatGPT prompt screenshot, reads: "Not bad. But try something more clever, more witty, and a little funnier. Tap into techniques used by standup comedians. An underwhelming, deadpan tone would work here."

Not bad. But try something more clever, more witty, and a little funnier. Tap into techniques used by standup comedians. An underwhelming, deadpan tone would work here.

And another time, I prompted it like this:

ChatGPT prompt screenshot, reads: "It's not funny enough. Try something more witty. On a 404 page you can use puns, sarcasm, deadpan, and even cheesy language. Also, keep your sentence shorter. Make them less wordy."

It's not funny enough. Try something more witty. On a 404 page you can use puns, sarcasm, deadpan, and even cheesy language. Also, keep your sentences shorter. Make them less wordy.

Just as I did above, you should always tell ChatGPT what you don’t like about its previous output. Then give detailed instructions on what you want it to improve.

To get better 404-page copy, you can ask ChatGPT to:

  • Write in the style of a standup comedian. Try giving specific names (e.g., Jim Gaffigan, Gabriel Iglesias, Chris Rock, Jimmy Fallon, Jim Carrey—have fun!)
  • Use specific literary or rhetorical devices like “underwhelmed,” “deadpan,” and “self-deprecating”
  • Be more clever, witty, direct, nonchalant and less wordy

You can also try starting a brand-new thread and entering the exact same prompt and exact same brand information. When it comes to humor, ChatGPT can get pretty creative, so you’ll get a different angle just by cleaning the slate.

I tried this AI prompt for a soap brand and a B2B message-testing site. Here’s what happened.

The soap brand Dr. Squatch is known for their hilarious video ads of men showering in the wilderness.

Given their brand play, I was surprised they had a standard 404 page. What a missed opportunity!

When I seeded brand information into ChatGPT 4, I was pleasantly surprised at how on-brand the output was. Check this out:

ChatGPT output for 404 page copy for the soap brand Dr Squatch

With just a bit of tweaking, I tried it on the website:

404 page concept for Dr Squatch soap brand. 
Headline: Whoops! Looks like you've wandered into the wilderness...
Body copy: Yep, you've found our uncharted territory. ... Let's get you back to civilization.
CTA: Back Home

The thing is, once you have that golden idea, you can run with it. Every copywriter knows, writing’s the easy part. It’s generating the big idea that’s hard. (Especially if you’ve written a company’s entire site and you don’t have much left in the tank for a 404 page.)

Rewriting ChatGPT’s draft takes seconds or minutes.

And so I played around with it to get this:

404 page concept for Dr Squatch soap brand. 
Headline: You've just stumbled upon our nether regions
Body copy: Whatever you were looking for, it's not here. Our bad! Let's get you back to decency.
CTA: Back Home

You can use ChatGPT 4 to write 404 pages for B2B companies too.

I was surprised Wynter, a message-testing platform for B2B SaaS, didn’t do something creative with their 404 page. It’s got a generic line, “This page doesn’t exist”:

Screenshot of current and original 404 page on Wynter.com

This would be a great place to inject some of Peep Laja’s dry humor.

I entered the same prompt I showed you. And after a couple of simple requests to fine-tune, ChatGPT 4 gave me this:

Screenshot of ChatGPT output for a possible 404 page for Wynter.com

Boom! I loved the idea of an “un-testable page”! Well done, ChatGPT 4!

It did the hard work of coming up with the idea, in seconds. And now I had something solid to work with.

In just a few moments, I reworked it to this:

Screenshot of edited 404-page copy for Wynter.com

ChatGPT 4 is really like a junior copywriter. Yes, the copy can be a bit half-baked. But with a solid idea in hand, you can work some magic in minutes.

Please note: I tried this same prompt in ChatGPT-3.5, but the results weren’t as clever or on-brand. But again, all you really need is a workable concept.

Why all this fuss about how to write 404 pages?

Your 404 page is a great place to admit you’ve messed up. It makes your brand human. It makes you likeable. It’s a great place to break the fourth wall.

Broken links will happen. Rather than lose a lead, use that moment to connect with your visitor on a human level. Smiles lead to open wallets.

For more cool tips on how to write 404 pages, hop on over here.

Have fun!