Hey Riddle Riddle – Patreon Preview #357: Phrase the Roof 4

Host: Headgum
Date: January 9, 2026
Cast: Adal Rifai, Erin Keif, John Patrick Coan (JPC)
Note: This summary covers the Patreon preview content, skipping sponsored ad reads, intro/outro, and promo material.

Episode Overview

In this special Patreon preview, Adal, Erin, and JPC hunker down for another round of “Phrase the Roof,” a recurring segment where the trio explores the origins of everyday phrases and idioms. They guess at meanings, invent hilarious backstories, and improvise scenes inspired by the phrases’ supposed histories.
As always, the focus meanders between earnest attempts at etymology, sharp improvisational comedy, and absurd flights of fancy, making for a laugh-filled, loosely riddle-adjacent episode.

Key Discussion Points & Insights

1. Setting the Scene: Cozy Entrances and Narnia References

• [01:10] The cast imagines entering a cozy room—immediately riffing on Mr. Tumnus from The Lion, the Witch and the Wardrobe, launching playful banter about his moral character.
• Notable tangent: They speculate (with increasing absurdity) on which Narnia characters meet first and the grossness/merits of Turkish Delight candy.

“I go fucking crazy for, like, with the jus. Like a Wet Lucy meets. Oh, my God.” – Erin [02:16]

2. Worst Candy Debate

• [02:35] Erin launches an anti-macaron rant, confusing the French treat with other similar-sounding desserts.
• The group agrees that Turkish Delight is notably disappointing, then gets tangled in the many meanings of “macaron.”

“That's the French president.” – Erin cracks, confusing “macaron” with Macron [03:12]

3. Introducing “Phrase the Roof”

• [03:27] Adal sets up the core game: guessing the origins and meanings of phrases like “take down a peg.”
• The podcast's tone: irreverent but curious—ready to detour at any opportunity.

4. Phrase 1: “Take Someone Down a Peg”

• [05:27] The trio speculates wildly:
  • Erin: It’s about pirate ships or…something to do with “going down on someone while they're pegging you.” [05:46]
  • JPC: Suggests a literal peg in the wall.
  • Adal: The answer—flags on ships were raised or lowered via a pegged system to denote status.

“Take Someone Down a peg originates from early sailing days when a ship’s flags were raised and lowered by pegs. The ships that were most important used the highest pegs to signify their rank.” – Adal [06:44]

Improvised Scene: The Ranking Pirate Captain

• [07:19] In classic Hey Riddle Riddle style, the gang enacts a scene where a pirate captain ranks his crew, MySpace Top 8 style—complete with sycophantic co-captains and overboard mishaps.

“You go ahead and jump off the ship, kill yourself.” – JPC, in pirate captain mode [08:24]
“Okay, we're on land, so that'll definitely kill me.” – Erin [08:30]

5. Next Phrase: “The Full Monty”

• [13:01] The show pivots to discuss the origin of “The Full Monty.”
• Erin jokes: “That is showing someone your Pendis, I believe.” [13:14], quickly descending into riffing on whether “Monty” is British slang or the name of a celebrity.
• Adal explains: The phrase comes from 20th-century UK tailor Sir Montague Burton, referring to a full three-piece suit.

Improvised Scene: Monty Burton in Heaven

• [14:14] The crew role-plays as heavenly souls comforting Sir Montague about his name’s fate.

“Now it’s like flashers and kind of like male exotic dancers... Thunder from Down Under. You know, that kind of stuff.” – JPC as Monty [15:06]

6. Memorable Quotes & Moments

• On Narnia Lore:
  “Don't Mr. Tumnus us. That would be strike three.” – Erin [01:29]
• On Mad Men:
  “I wonder if it's ready for a rewatch on the old Mad Men. Have I forgotten enough... that I could enjoy watching it again?” – Erin [05:00]
• On Phrase Origins:
  “Ricky Gervais, the Invention of Riddles. I love that movie.” – Erin [04:12]

Notable Quotes with Timestamps

| Time | Speaker | Quote | |----------|---------|-----------------------------------------------------------------------| | 02:16 | Erin | “I go fucking crazy for, like, with the jus. Like a Wet Lucy meets.” | | 03:12 | Erin | “That's the French president.” (confusing ‘macaron’ with Macron) | | 05:46 | Erin | “When you’re going down on someone while they’re pegging you?” | | 06:44 | Adal | “Take Someone Down a peg originates from early sailing days…” | | 08:24 | JPC | “You go ahead and jump off the ship, kill yourself.” | | 08:30 | Erin | “Okay, we’re on land, so that'll definitely kill me.” | | 13:14 | Erin | “That is showing someone your Pendis, I believe.” | | 15:06 | JPC | “Now it's like flashers and kind of like male exotic dancers…” |

Timestamps for Important Segments

• [01:10] – Cozy room setup, Mr. Tumnus/Narnia references
• [02:31] – Turkish Delight and worst candy debate
• [03:27] – Adal introduces “Phrase the Roof”
• [05:27] – First origin guessing: “Take (someone) down a peg”
• [07:19] – Pirate captain improv scene
• [13:01] – The “Full Monty” discussion
• [14:14] – Sir Montague Burton in heaven improv

Episode Tone & Takeaways

Style & Humor:
The trio’s trademark chemistry shines, blending (mis)education with offbeat improv and heartfelt camaraderie. The riddles and etymology are a launching pad for their sharp banter and absurdist scenes.

Useful For:
Anyone curious about phrase origins (with a heavy comedic slant), fans of improv, or listeners who love winding, organic conversations more than strict riddle-solving.

Summary

This episode sees Adal, Erin, and JPC deep in etymological waters, cracking each other up over the hidden—and often ridiculous—histories of common English idioms. If you've ever wondered where “full Monty” or “take down a peg” come from and enjoy hilarious “what if?” scenarios about flag-waving pirates or misunderstood tailors, Phrase the Roof 4 captures Hey Riddle Riddle at its riddle-light, improv-heavy best.