I’ve worked in several industries in my life, and every one has had its share of jokes.  Some were as old as the hills, and some were wisdom disguised as humor.  Quite a few were ribald, particularly if you were in the more blue-collar end of the business.  If people work long enough at something, someone eventually is going to invent or adapt a joke.

The other day I realized I’ve never heard any web hosting jokes.  I’ve heard a lot of humorous discussion about web hosting, but never heard a joke about web hosting in the sense of a “two servers walk into a bar” kind of joke (i.e., a joke you would tell and pass on).

I googled and came up dry.  Half the results were about hosting in the “Conan O’Brien was hosting the Oscars once” sort, and most of the web hosting jokes were really more awkward puns.

AI To The Rescue?

Perhaps AI can help.  I asked it “tell me a funny joke about the web hosting industry or working in that industry.”

The results were…painful.

They reminded me of when my daughter was a toddler and just getting the idea of humor.  She got the idea that people laughed if you told and joke and wanted to try it.  In her mind, you say some things, and then you say something else that takes a sharp turn in the story and that’s funny.  A typical joke from this era went something like this: “the dog was running across the field chasing a ball when suddenly a rabbit jumped out of its hole and and said ‘Happy Stick Chasing Day!'”

You could sort of see the gestalt of humor there.  There was a setup and an unexpected juxtaposition of a related-but-different idea, etc. but it wasn’t funny.  She had the bare bones idea of how to write a joke but couldn’t quite pull it off.  Humor is not an easy concept.

And it’s one that AI just doesn’t get.

Here’s an example of a ChatGPT joke based on that prompt:

A developer is interviewing for a DevOps role.

The CTO asks, “Can you scale infrastructure cost-effectively?”

The dev smiles confidently and says, “Absolutely. I once ran a full CI/CD pipeline, WordPress multisite, mail server, and monitoring stack on a $3 VPS.”

The CTO leans forward: “…And did it work?”

The dev shrugs.

“It worked great until I installed a web-based file manager. Then it caught fire, emailed me its error logs, and deleted itself to save resources.”

The setting is actually good, and the “leans forward” moment for the punchline is great, but it completely falls flat because the punchline makes no sense.

Here’s another:

On Christmas Eve, a sysadmin falls asleep at their desk.

At 3 a.m., they are visited by the Ghost of VPS Past — a dusty Pentium II running Debian Etch.

The ghost says, “You promised 99.9% uptime… and never backed up /etc.”

Then comes the Ghost of VPS Present — a wheezing container on an oversold node in Buffalo.

“Behold,” it says, “your users waiting 11 seconds for a PHP page to load.”

Finally, the Ghost of VPS Yet to Come appears.

It shows a blazing NGINX stack… running in a data center powered by blockchain AI, costing $900/month.

The sysadmin wakes up in a sweat, deletes his cronjob for compiling LibreOffice, and sets up rsnapshot.

Ugh.  Classic three-part setup, and each step of the familiar Christmas Carol story is nicely translated into tech speak (and even a minor shot at an “oversold in Buffalo” – that’s the funniest part, actually).  But the punchline makes no sense.

I tried this prompt multiple times, and AI just couldn’t deliver.  I tried Grok as well…feel free to glaze over this paragraph because it’s not funny:

A web hosting employee walks into a bar after a long day, looking frazzled. The bartender says, “Rough day, huh? What do you do?” The employee sighs and says, “I work in web hosting, managing servers for a big provider.” The bartender, intrigued, asks, “Oh, so you keep the internet running? Sounds intense! Tell me more.” The employee chuckles and says, “Well, picture this: I’m babysitting thousands of websites, and they’re like needy toddlers. One minute, they’re all happy, serving pages smoothly. The next, a client’s site crashes because they tried to upload a 5GB video of their cat to their $5-a-month shared hosting plan. Then, another client calls at 2 a.m. screaming, ‘My site’s down!’ Turns out, they forgot to renew their domain. And don’t get me started on the guy who thought ‘unlimited bandwidth’ meant he could stream his entire movie collection to the world. By the end of the day, I’m just praying the servers don’t throw a tantrum and go offline to spite me!” The bartender laughs, pours a drink, and says, “Mate, sounds like you’re not just hosting websites—you’re hosting chaos!”

…um, yeah.

In my experience, AI does very well at writing funny poems – just ask it to create a limerick.  It does passably well at writing short stories, outlining novels, or crafting movie treatments.  I’m not saying that they’re Pulitzer- or Oscar-worthy but at least they’re competent.

But it appears that humor is still a field where humans are better than AI.

Although…

One Savage Success

There was one joke that ChatGPT made that was actually pretty funny:

What do you call a VPS with no RAM, no CPU, and no bandwidth?

“Still better than GoDaddy.”

LOL!

So have you heard any good web hosting jokes?  Jokes in the industry?  Please leave some in the comments below!

raindog308

Raindog308 is a longtime LowEndTalk community administrator, technical writer, and self-described techno polymath. With deep roots in the *nix world, he has a passion for systems both modern and vintage, ranging from Unix, Perl, Python, and Golang to shell scripting and mainframe-era operating systems like MVS. He’s equally comfortable with relational database systems, having spent years working with Oracle, PostgreSQL, and MySQL.

As an avid user of LowEndBox providers, Raindog runs an empire of LEBs, from tiny boxes for VPNs, to mid-sized instances for application hosting, and heavyweight servers for data storage and complex databases. He brings both technical rigor and real-world experience to every piece he writes.

Beyond the command line, Raindog is a lover of German Shepherds, high-quality knives, target shooting, theology, tabletop RPGs, and hiking in deep, quiet forests.

His goal with every article is to help users, from beginners to seasoned sysadmins, get more value, performance, and enjoyment out of their infrastructure.

You can find him daily in the forums at LowEndTalk under the handle @raindog308.