Episode Overview

Podcast: Myths and Legends
Episode: 422: Scottish Folklore: Witchful Thinking
Date: November 19, 2025
Hosts: Jason Weiser, Carissa Weiser

This episode explores a collection of witty and subversive Scottish (with a nod to Norway) fairy tales focused on witches, wizards, and the unsuspecting mortals who encounter them. With Jason's signature deadpan humor and metafictional commentary, the stories challenge familiar tropes—recasting heroes and witches alike with modern attitudes and flawed motives. From milk that magically flows from a wall to fortune-seeking pub owners outwitting powerful wizards, the episode is both a rollicking magical adventure and an exploration of agency and expectations in folklore.

Key Stories & Discussion Points

1. The Tale of the Traveling Tailor and the Milk Witch (00:01–18:45)

• Setup: A young, itinerant Scottish tailor arrives at a farmhouse for work. Daily breakfast here seems odd: milk is magically abundant and always fresh.
• Key Moment: The tailor witnesses the farmer's wife using a wall pin to summon milk, deduces she’s a witch, and exposes the secret (10:50).
• Chaos Ensues: The tailor, eager for popularity, throws a “milk party” using the magical pin, accidentally unleashing an uncontrollable milk flood.
• Consequence: The witch returns, angry, and metes out a just punishment—forcing the tailor to mop up the mess, then magically threatens him with a Sisyphean cleaning fate should he fail (15:50).
• Themes: Meddling with forces one doesn’t understand, the cost of popularity, the banality and pettiness of everyday magical folk.

Notable Quotes:

• “If your milk feels especially sharp or pin like, it is not in fact milk, that’s a pin, and you shouldn’t drink it.” — Tailor, (14:20)
• “‘You will clean this entire house, or I’ll turn back time and make you clean it again, over and over until it’s perfect,’ she said.” — Witch, (15:58)
• “You know what? I don’t want this. I don’t like being the main character. It’s horrible. I just want to do my job and not go through these challenges and grow and all that nonsense.” — Tailor, directly breaking the fourth wall, (17:20)

2. Gilly MacDonald and the Wizard’s Castle (18:46–1:01:50)

Segment Breakdown:

A. The Call to Adventure (18:46–25:10)

• Gilly MacDonald, an innkeeper, hears from a drunken peddler about rumored gold hidden at the castle of Tacronin, guarded by a dangerous wizard. Gilly, restless and feeling out of place in his conventional life, impulsively sets out for adventure.

Quote:
“He enjoyed the companionship of the tavern, but he felt this pull towards something new and big and different. The castle.” — Jason (Host), (05:20)

B. Encounters on the Road: Witch Hunters and Magic Cats (25:11–34:30)

• Strange Meetings: Along the way, Gilly repeatedly meets a small, mysterious acrobat (in various guises) who cryptically echoes the phrase “We are fellow travelers. For the present.”
• Witch Hunter’s Tale: Gilly is regaled with a grim Norwegian tale of witches, where a supposed witch (in the form of a cat) is exposed after a silver bullet or a severed animal limb corresponds magically with an injured or mutilated villager.

Quote:
“Isn't the former bringing in a woman killed by a silver bullet, claiming she had been in animal form when shot? Isn't that ripe for abuse? What's to stop someone from just shooting people and claiming they were witches?” — Gilly (Host as Gilly), (32:40)

C. The Magical Obstacles (34:31–47:40)

• The Acrobatic Shapeshifter: Gilly is repeatedly confronted by the acrobat in ever more bizarre forms—hunchback, giant tree, literal giant, and finally as a cliff-face itself, always with the foreboding promise: “We’ll meet again, maybe before long.” (38:30, 41:40, 44:55)
• Atmospheric Pause: The show comments on the unsung terror of adventure—the long, lonely, and uncanny bits the old tales tend to skip.

D. The Wizard’s Castle: Outwitting the Magician (47:41–1:01:50)

• Capture: Gilly is seized by the wizard (proving to be a powerful shapeshifter), forced into servitude as a digger in his castle.
• Verbal Chess Match: Gilly feigns servitude, slyly invents a story about being tracked by an even greater master, unnerving the wizard (53:10).
• The Wizard’s Desperation: Fearing Gilly’s “master,” the wizard attempts increasingly silly and ineffective hiding places, shrinking himself repeatedly at Gilly’s urging.
• Resolution: Ultimately, Gilly “steps” on a beetle (the wizard in his tiniest form), apparently killing him (59:20).

Notable Quotes:

• “Not his deal. He was here to serve the wizard well, whichever wizard was the strongest.” — Jason as Gilly (54:25)
• “Hey, you can lie to me all you want, but just be sure you’re not lying to yourself. Because that’s how people get crushed by giants.” — Gilly to the wizard, (59:00)

E. The “Win Five Princesses” Absurdity (1:01:51–1:15:30)

• Rescued Maidens: Five princesses (the wizard's captives) rush to thank Gilly as their “hero” and all propose to marry him at once.
• Subversion of Tropes: Gilly refuses—all attempts to force a marriage result in games, trick questions, and convoluted challenges; he ultimately slips away with the treasure while the princesses are distracted.
• Returning Home: Gilly escapes with the gold, outsmarts his would-be brides (with the help of loyal servant Lachlan dressed as a “good wife” to foil their pursuit), and comfortably improves his lot in life, unmarried but content.

Quotes:

• “I really don't think we're supposed to read anything more into the relationship between Gilly and his servant other than a very dedicated employee who wants to help out his boss by posing as his wife with Gilly. Gilly apparently knowing that was the line the five women would not cross.” — Jason's post-story commentary (1:16:20)

3. Reflections and Subversions (1:15:31–1:18:00)

Host Analysis:

• Jason notes the comedic subversion of classic fairy tale tropes—especially the way Gilly actively avoids marriage (even to five princesses intent on it), in stark contrast to most fairy tale heroes.
• The wizard's “ethics” are questioned (enslaving treasure-seekers, kidnapping princesses, yet oddly only punishing those who tried to rob him).

Quote:

• “It is interesting how the ‘win a Princess’s Hand’ trope was subverted by Gilly, who simply did not want to marry at all, going to great lengths to not marry not only one, but five, when seemingly every other male fairy tale protagonist will do anything to marry the princess.” — Jason (1:16:00)

Notable Quotes & Moments

• "If your milk feels especially sharp or pin like, it is not in fact milk, that’s a pin, and you shouldn’t drink it." — Tailor (14:20)
• “You will clean this entire house or I’ll turn back time and make you clean it again, over and over until it’s perfect.” — Witch (15:58)
• “We are fellow travelers. For the present.” — The shape-shifting acrobat/giant/cliff (recurring; first at 38:30)
• “Hey, you can lie to me all you want, but just be sure you’re not lying to yourself. Because that’s how people get crushed by giants.” — Gilly (59:00)
• “If he remained unmarried, it was not for lack of offers.” — Jason (1:15:50)

Timestamps for Key Segments

• 00:01 — Opening and episode premise
• 03:00 — Introduction to Gilly MacDonald and his motivation
• 10:50 — Tailor witnesses the milk witch
• 15:50 — Tailor’s punishment by the witch
• 25:15 — Gilly encounters the witch hunter & magic cat story
• 38:30 — Recurring meeting with the mysterious acrobat/giant
• 47:50 — Gilly captured by the wizard
• 53:10 — Gilly tricks the wizard
• 59:20 — The wizard’s tiny demise
• 1:01:50 — Five princesses demand marriage
• 1:11:45 — Gilly orchestrates his escape & homecoming
• 1:16:00 — Jason’s closing analysis/subversions of fairy tale tropes

Tone and Style

The episode, narrated primarily by Jason, is fast-paced and snarky, loaded with contemporary asides, fourth-wall breaks, and laughter at the weird logic of folklore. Characters speak in a playful, modern cadence, often calling out the structure or absurdity of their own stories (“You know what? I don’t want this. Go on. Go on, git. You leave if you know what’s good for you.” — Tailor, 17:20). The humor is dry and metafictional, poking fun at premise, plot, and even the podcast structure itself.

Summary Takeaways

• Scottish folklore’s witches and wizards are as canny, cunning, and flawed as the mortals who contend with them.
• Subversion of familiar tropes (winning the princess, the noble hero) is at the heart of these stories—heroes may very well choose gold and freedom over romance or glory.
• The dangers in these tales come as often from boredom, awkwardness, and magical bureaucracy as from dragons or curses.
• The episode is as much about how stories are told—and retold with a wink—as about the stories themselves.

This episode exemplifies Myths and Legends’ blend of rich folklore, sharp humor, and cultural analysis, serving up enchanting and offbeat tales with a thoroughly modern sensibility.