Month: June 2025

We had a long-overdue game of Dungeons and Dragons at our place on Saturday, and we did it old school/new school, or as I like to say, we took the “Flintstones/Jetsons approach.”

If you think D&D’s just a silly game, I need to remind you that it’s part of the foundation of nerd culture, and as a result, it’s baked into the DNA of the technology industry. Reid Hoffman, who made a little website you might have heard of — LinkedIn — insists that Dungeons and Dragons made him the business success that he is today, and that it’s a valuable tool for learning about making your way in the business world.

He’s even devoted a couple of episodes of his podcast, Masters of Scale, to the topic. Here’s the latest one:

If Hoffman’s endorsement doesn’t impress you, how about Vin Diesel’s?

Or Joe Manganiello?

Or the cast of Daredevil?

Old school

The “old school” part was that we played the 1980s edition of D&D: Advanced Dungeons and Dragons, First Edition, written by E. Gary Gygax himself! This was the version of D&D depicted in Stranger Things…

…and yes, it’s the version that was part of the “Satanic Panic” and one of my favorite Jack Chick tracts, Dark Dungeons…

It also led to Tom Hanks’ most unintentionally funny movie, Mazes and Monsters, a 1982 made-for-TV movie (based on Rona Jaffe’s novel of the same name) that put the scare into a lot of parents about the game:

The first edition rules are quaint by today’s standards, but they’re still recognizable by people who play using the current version — the 2024 revision of the Fifth Edition rules. After all, the rules and dice are there to provide a basic structure; the game is really about the shared storytelling experience.

o my nearly-complete set D&D books from the ’80s (I’m missing Deities and Demigods), and brought them to Tampa from Toronto. I even have two copies of the original edition Dungeon Master’s Guide.

We had one last old school element for our game: Cheetos and Mountain Dew:

In case you don’t get the reference, it’s from this video…

…whose dialogue is a snippet from this skit (which also pokes fun at the Satanic Panic) by the Dead Alewives:

New school

The game monitor

You can play Dungeons and Dragons without any visual aids; it is storytelling, after all. But sometimes, it’s nice to be able to provide players with a sense of where they are, and where other characters in the game are.

Many games are conducted with maps and miniatures, starting with simpler setups like this one…

…to fancier setups like this one, for sale on Etsy at the time of writing:

I wanted something that could display maps, but also provide visuals, and even play mood- and scene-setting music and video:

I used a monitor that I’ve owned since 2008 that I’d been saving for hobby audiovisual projects. I removed it from its stand so that it could lay flat, and I put some stick-on felt pads on its back so it wouldn’t scratch up the table:

There’s just enough room on the back of the monitor for me to attach a Raspberry Pi and turn it into a dedicated “smart tabletop,” but for the time being, I simply connected it to a laptop.

Here’s the monitor on our dining table to give you a sense of size and scale:

I created a whole set of maps, some taken from online sources, and some taken from the “Game Master’s Guide” series of books (on sale for $15 at Humble Bundle at the time of writing):

And I assembled them into a Canva project. During the game, I used Canva’s presentation mode to present an introduction to the gaming session:

This “slide” was actually video. It didn’t show more than the “Chaper 1” title and a camera panning across a foggy forest:

I originally thought about using a city from the old The Keep on the Borderlands “module” — a pre-scripted adventure that you can buy — but decided that in the age of AI and other technological wonders, I could do better.

First, I decided to take inspiration from the decade when I started playing D&D, the 1980s and adapt characters and ideas from that era.

The map generator

With that in mind, I created a starting point: the city of Ferris (as in Bueller). I went to the Medieval Fantasy City Generator site, where I was going to have it generate a city for me, but I was rather fond of one of their examples, so I simply used the example and added some additional text and labels to it:

My “dice”

I don’t own any dice (Anitra does, but I don’t), so I used the DnD Dice Roller, which is very useful for DMs, since it keeps a log of all your rolls.

(Also, using it makes it very easy to do surreptitious  die rolls that the players don’t know about!)

Claude and Canva

I then opened Claude, uploaded the map, and entered this prompt:

I’d like to use the city depicted in the attached map as the initial setting for the adventure. Can you come up with descriptions of the areas in the map that fit my “D&D 1980s homage” setting?

Claude, being a very good AI, processed the map and starting generating descriptions of each area. Here’s a sample:

FEY ALLEY (Central District)

The heart of the city’s entertainment and nightlife scene. This is where The Iron Maiden is located, along with other music venues, theaters, and upscale taverns. The district pulses with energy day and night – think neon-lit (magical crystal) signs, street performers, and the constant sound of music. The architecture mixes elegant older buildings with newer, flashier establishments. During the day it’s respectable; at night it transforms into the city’s party central where adventurers, artists, and risk-takers gather.

Key Features:

• The Iron Maiden tavern and music venue
• Several smaller clubs and performance halls
• Magical “neon” lighting powered by enchanted crystals
• Street art and graffiti that occasionally moves or changes
• The Vinyl Vault – a shop selling recorded music on enchanted crystals

---

DUSKPOLE (Western District)

The city’s administrative and political quarter, housing government buildings, courts, and official residences. Named for the ornate streetlamps that create dramatic lighting at sunset. This district has a more formal, uptight atmosphere – lots of bureaucrats, lawyers, and minor nobles trying to look important. The buildings are impressive but conservative, representing established power.

Key Features:

• City Hall and administrative offices
• The Hall of Justice (courts and legal proceedings)
• Government archives and records offices
• Exclusive gentlemen’s clubs for the political elite
• The Establishment – an ultra-conservative tavern that [one of my key NPCs] would never set foot in

I would start my players in a tavern in Fey Alley (Ferris’ entertainment district) called The Iron Maiden, which would be the D&D version of a club you’d go to see up-and-coming rock acts.

Here’s a portion of the prompt I used to flesh out TYhe Iron Maiden:

I need an opening scenario for my first-level party where they’re making their first steps as adventurers. I want to start with them at a tavern (of course) called The Iron Maiden, trying to see if there are any opportunities for adventure. I want them to be approached by someone recruiting for [Redacted].

This tavern should be the World of Greyhawk’s equivalent to the kind of bar where you’d see a combination of up-and-coming bands and general mayhem. Think of the club where the band Dragon Sound plays in the film Miami Connection.

For the main staff of the Iron Maiden, I need 3 characters, modeled after Jack, Chrissy, and Janet from Three’s Company. Jack is the bartender, and Chrissy and Janet are the waitstaff.

Here are the screens I used for The Iron Maiden:

I used Canva’s AI feature to generate this image of a band playing a heavy metal-like style of music that’s new to the D&D world:

I used a combination of Claude (for fleshing out the character backstories and generating stas) and Canva AI (for generating images) to create characters such as the dealmaker…

…this mysterious individual…

…and an incredibly capable, if dysfunctional band of adventures modeled after Fleetwood Mac:

Here’s a portion of what Claude gave me in response to my prompts:

Mick is the steady foundation that keeps the group together despite their personal chaos. As the group’s founder and leader, he’s learned to navigate everyone’s explosive personalities while maintaining their professional reputation. He’s the diplomat, the mediator, and often the only thing preventing the group from imploding…

Stevie is the group’s mystical heart and soul. Her elven heritage gives her an otherworldly perspective, while her dual-class abilities make her incredibly versatile. She’s intuitive, mysterious, and has a tendency toward dramatic pronouncements that sometimes prove prophetic…

And no 1980s-themed adventure is complete with one Mr. William Broad, an up-and-coming bard…and maybe more:

I gave Claude plenty of prompt info, and I got a nice little backstory in return:

Born Wilhelm Broad in the Free City of Greyhawk, he was the son of a minor noble who expected him to follow a traditional path. Instead, he was drawn to the taverns and street corners where real music lived. He adopted the stage name “Billy Idle” after a particularly scathing review called his political ballads “the idle complaints of a spoiled brat.”

Billy spent years traveling the Flanaess, learning songs and stories from every culture. He’s performed in the courts of Furyondy, the taverns of Dyvers, and the underground clubs of the Free City. Along the way, he’s accumulated contacts, debts, favors, and a reputation as someone who knows everyone and everything.

The players’ first hint about the campaign’s “Big Bad” were these runic markings:

Thanks to a couple of evenings’ worth of work with Claude, Canva, and the kind of imagination that thinks that walking around with an accordion is a good idea, I came up with all sorts of scenarios and encounters, all designed to push the story forward.

The players were sent to investigate a mill that was suddenly producing poisoned flour…

…which led them to an abandoned temple, where two religious cultists were casting a spell that could adulterate all food and kill vegetation and small animals in a three hundred yard radius:

When the players did something I didn’t expect and I needed to create a new setting in a hurry, I gave Claude some quick prompts and got what I needed.

For instance, when they decided to leave The Iron Maiden and find a more down-to-earth working-class pub, I fed Claude a prompt which included the following information.

Claude and I had been having an ongoing “conversation” about the city of Ferris, so it had enough context for the following prompt to work:

• I need a working class-type pub located in Frohman right by the river.
• Give it an appropriate name.
• Use the cast of Cheers as a template for the people there. I need stats, too.

Also keep in mind that [redacted, because the players haven’t hit that point in the story yet]…

This is only a part of the description I got back, and all in about a half-minute of prompt typing and another half-minute of generation:

The Setting

The Rust & Ruin sits on Hammer Street, just three blocks east of the main bridge crossing the River Sloane. It’s perfectly positioned to catch workers heading home from the docks, warehouses, and workshops that line the river’s eastern bank. The building faces west, so workers can watch the sunset over the river through the windows while enjoying their after-work drink.

The Building

A solid, two-story stone and timber structure that’s clearly built to last rather than impress. The walls show honest wear from decades of use, and the slate roof bears patches from various repairs. The pub sign hangs from a wrought-iron bracket: a painted shield showing a hammer crossed with a tankard, both showing realistic rust and wear that somehow looks dignified rather than shabby.

Street Presence

Unlike the entertainment venues in Fey Alley, The Rust & Ruin doesn’t try to attract attention. The windows glow warmly at night, voices and laughter spill out onto the street, and the smell of hearty food draws in the hungry. A simple wooden bench sits outside for those who want to rest weary bones or enjoy a pipe in the evening air.

Practical Details:

• Hitching posts for delivery wagons and work animals
• Boot scraper by the door (and it gets used)
• Rain barrel to wash dusty hands before entering
• Simple but sturdy construction throughout

Afterward…

Our session lasted from 1:00 to 7:00 p.m., after which we went out to dinner at Retro House (very appropriate, since it was a retro-themed D&D campaign) for Chinese food…

Retro House has a board game night every Wednesday, and that’s probably why they had this thing near their front door:

…a gumball machine that dispenses dice for a quarter! Anitra and I came back the next day with a large handful of quarters and got a nice haul.

And afterward…

It was Saturday night, so why go home when you can go to the Spookeasy Lounge…

…have a beer, and then go down to The Catacombs for some classic goth, alt-rock, and Prince tunes, and as one does in a place called “The Catacombs” when you’ve been Dungeon Mastering all afternoon…

All in all, a fun day for me (and hopefully the players, too!).