A Week Of Medieval Puns And Ink-Stained Dragons

My week drawing fifty medieval puns began with a blank page, a sharpened pencil, and the uncomfortable knowledge that “knight shift” was already doing a lot of heavy lifting. The assignment sounded simple: create a batch of jokes with castles, dragons, peasants, jousting, and enough wordplay to fill several pages. The reality was a siege conducted against my own brain.

Medieval comedy has useful ingredients. Everyone carries a sword, every building looks slightly uncomfortable, and a misplaced letter can turn an ordinary sentence into a terrible gag. The difficulty is making each pun feel like a cartoon rather than a sentence wearing a cardboard helmet.

I treated the week as a miniature creative campaign, moving between rough sketches, captions, character designs, and increasingly desperate cups of tea. Somewhere among the bishops, blacksmiths, and suspiciously confident dragons, the drawings began to find their rhythm.

The Brief Arrives With A Tiny Sword

The first job was to work out what “fifty medieval puns” actually meant. Fifty finished cartoons would be a substantial stack of drawings, while fifty individual jokes could be arranged into mini-strips, single-panel illustrations, or a longer comic sequence. I made a list of possible settings and started pairing them with words that sounded vaguely old-fashioned.

A castle became a natural workplace for bad management jokes. The dungeon offered opportunities for low morale, poor ventilation, and awkward career development. The village supplied shopkeepers, stable boys, travelling minstrels, and one extremely overworked person responsible for putting hay in every background.

The strongest ideas had a visual engine attached to them. A pun about a knight could become a dented helmet, a horse with attitude, or a squire carrying the wrong object. If the joke only worked when read aloud, it went into a separate pile marked “possibly useful, probably cursed.”

Finding The Joke Beneath The Armour

Writing the captions came before the detailed drawing. I filled pages with phrases involving jousts, feasts, shields, heraldry, dragons, monks, and medieval occupations. Some were pleasantly groan-worthy. Others collapsed so completely that they seemed to require a priest, a physician, and a small burial plot.

The trick was to keep the language clear. A cartoon has very little room for explanation, so the picture must support the wordplay immediately. A knight staring at a cracked lance communicates more than a paragraph about equipment failure. A dragon guarding a pile of paperwork tells its own story before the caption arrives.

That balance is familiar from work such as medieval photocopier, where an ordinary modern frustration becomes funnier when placed in an unexpected historical setting. The period supplies the costumes, but the joke usually comes from a recognisable human problem.

A Castle Full Of Roughs

By the second day, the desk looked like an archaeological dig. Sketches were layered over rejected captions, reference books were opened to pages I no longer remembered consulting, and every available margin contained a tiny helmet. I drew characters quickly at first, looking for silhouettes that could carry a joke without needing elaborate scenery.

The dragon proved especially useful. It could be enormous or pocket-sized, dignified or sulky, terrifying or plainly bored. A dragon waiting for a delayed delivery had a different comic energy from one attempting to complete a tax return, but both benefited from the same basic rule: give a powerful creature an irritatingly ordinary problem.

This was also where the historical details had to be restrained. Authentic clothing and architecture can add flavour, yet too much accuracy turns a punchline into a museum display. I wanted a medieval world that felt convincing for three seconds, then happily fell apart.

Fifty Ideas On The Drawing Board

The working list became easier to manage when I sorted each idea by the part of the cartoon doing the heavy lifting. Some relied on a caption, some on a visual twist, and some on a character reacting in exactly the wrong way.

Joke ingredient	Useful setting	Drawing problem
Knightly language	Jousting ground	Make the action readable
Castle bureaucracy	Great hall	Fill the scene without clutter
Dragon behaviour	Cave or village	Keep the creature expressive
Medieval trade	Market square	Give every stall a clear purpose
Food and feasting	Banquet table	Avoid burying the punchline
Music and minstrels	Tavern or courtyard	Make the sound visible

The sorting process revealed which puns were genuinely promising and which were simply words I had become too tired to reject. A good batch needs variety: recurring characters, different locations, short captions, visual surprises, and a few jokes that are so silly they become oddly memorable.

I also kept a separate page for possible strip titles. That is where George, the dragon, and a few troublesome peasants began to acquire personalities. Once a character has a face, posture, and favourite complaint, the drawing becomes quicker because the joke can be filtered through someone specific.

When The Characters Take Over

By the middle of the week, the cast had started making decisions without permission. The knight refused to look heroic unless he was carrying something inconvenient. The dragon preferred office work to treasure. A medieval schoolmaster appeared in several sketches, each time looking more exhausted than before.

That sort of repetition can be useful. Recurring figures create a visual shorthand, allowing the reader to recognise the setup before reaching the punchline. It also gives the artist a break from inventing a new face for every gag, which matters when the schedule involves dozens of small drawings.

The influence of comic strips such as George vs Dragon, Boo!, Carrotty Kid, and Bad Grandad sits in that meeting point between a simple premise and a strong character reaction. The setting may be fantastical, but the emotional response should remain familiar: annoyance, pride, confusion, panic, or the quiet dread of being volunteered for something.

The Last Inks Go Down

The final day was devoted to tightening captions, cleaning silhouettes, and removing details that had seemed clever at midnight. Medieval scenes can become crowded very quickly. A flag, a barrel, a chimney, three chickens, and a background castle may all be amusing individually, but together they can stage a hostile takeover of the joke.

I checked each drawing at a smaller size, because comic work often lives on a page where the reader sees the whole design at once. If the eye landed on the wrong face or object, the composition needed adjusting. The best punchline should not require a treasure map.

The last pun involved a knight, a queue, and a deeply unimpressed horse. It was not the most sophisticated joke of the week, but it had survived every edit. That made it feel like the right one to finish with: sturdy, visual, and just ridiculous enough to deserve a little armour.

Lessons From The Drawing Board

The week left me with a few practical rules for future batches of historical silliness:

• Start with visual situations, not just lists of words.
• Let the characters react strongly to ordinary problems.
• Keep period detail selective so it supports the gag.
• Read every caption aloud before committing to the final lettering.
• Save the strangest idea; it may become the most memorable drawing.

Fifty puns is a sizeable number, but the real challenge is giving each one a reason to exist. A medieval joke needs more than a castle-shaped backdrop. It needs a clear expression, a readable action, and a tiny spark of modern frustration hiding beneath the chain mail.

The finished drawings now feel less like a collection of ancient history jokes and more like a noisy little kingdom populated by people who happen to use swords. Visit Andy Fanton Dot Com to explore the comics, drawings, writing, and other odd corners of that kingdom, where the next terrible pun is likely already sharpening its quill.