Patreon Preview #357: Phrase the Roof 4

Summary

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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.

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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.

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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]

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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…” |

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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

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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.

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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.

Transcript

[A]

Hey, it's Tig Notaro from the Handsome Podcast.

[B]

And I'm Mae Martin.

[C]

And I'm Fortune Feimster, also from the Handsome Podcast. And we wanted to let you know that we made a very fun special episode of our show sponsored by Squarespace. That's up now on our YouTube page for you to watch.

[B]

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[C]

I feel like we can't say much more about it without giving too much away. So just go watch us make complete fools of ourselves and have the best time ever.

[A]

Or become the newest pop sensations.

[B]

That's right. Go to YouTube.com handsomepod or listen wherever you get your podcasts.

[C]

That's YouTube.com handsomepod to hear us record a song live. See you at the Grammys. Oh, for sure, buddy.

[B]

For sure. Get started on your dream website today. Head to squarespace.com handsome for a free trial, and when you're ready to launch, use the offer code handsome to save 10% off your first purchase of a website or domain.

[D]

Aaron, jpc. Welcome. Come on in. You must have had a long day.

[A]

Yeah. You look a little suspicious, but it smells good in here and there's nice music playing. I'm just gonna get all cozy and ready.

[E]

Yeah, yeah.

[D]

Sit by the fire and relax your feet.

[A]

Don't Mr. Tumnus us. That would be a strike three. Okay, Adel, just a quick reminder that you are at two strikes from Mr. Tumnusing us.

[D]

And. Okay. Having never read or seen you play.

[A]

Your magic flute and you lull us into his sleep, and then you bring us to the queen.

[D]

Yes. Let me just get out.

[E]

He did that shit, man. I knew there was a reason I didn't fuck with Mr. Tumnus no more. I hate hearing about. I hate hearing about people that I used to fucking Stan. Dirty, devious. Down, Dirty, devious shit.

[A]

They did pretty brutal stuff.

[D]

Is Mr. Tummus the first thing that the kids meet when they walk through the wardrobe?

[A]

Yeah, okay. It's the first thing Lucy meets. I'm not sure about everyone else.

[E]

Oh, dude, I love a Lucy meets sandwich. I go fucking crazy for, like, with the jus. Like a Wet Lucy meets. Oh, my God.

[A]

Wet Lucy meets Edmund meets the Queen first. And that's the Turkish Delight exchange. Mmm.

[E]

Oh, yeah. Turkish Delight. The candy. That sucks.

[A]

Yeah. It's not good.

[E]

It's not good.

[D]

Now I've had some. That's good.

[E]

Oh, interesting.

[D]

I've had some. That's bad.

[E]

What do you think is the worst candy? Like Turkish Delight is like. It's a thing. Like it's a type of candy that is not good to taste.

[D]

Bit o honey's up there.

[E]

Can I tell you something I honestly don't fuck with? It's a macaroon. Those are the ones that the French ones that are like pink and green and whatever. Not. Cause there's like four different things that are a macaron.

[A]

I love macarons.

[D]

And then macaron. Is that right?

[E]

That's the French president. But it is that. It's like there are three different things that sound like that.

[D]

Yeah.

[A]

Hmm. Hmm. At all. Why are we in this very nice, cozy room with you?

[D]

Well, I thought that we could revisit a little idea I had called phrase the roof. Takes out my flute.

[A]

Horseshoe, horseshoe, horseshoe, horseshoe, horseshoe, horseshoe.

[D]

To see where we get expressions like honk, shi. Oh, shit, they're asleep. Wake up. Wake up. Pours hot coffee on their foreheads.

[A]

Strike three. And strike one for hot coffee on my forehead. Because that's the first time you've ever done that.

[E]

Hopefully the last time I get hot coffee dumped on my forehead.

[D]

Of course. Raise the roof is an idea I had maybe for what this podcast would have been if not for the invention of riddles. So I'm gonna read out loud Ricky.

[E]

Gervais, the Invention of Riddles. I love that movie.

[D]

I just love that he says what.

[E]

He'S thinking, and I love that it's always just raw. You know, he takes religion down a peg just like Bill Maher.

[D]

So phrases like take down a peg. I'll read those out loud. You guys will have to guess what you think they mean or where you think they come from. I guess the origin story, and then I'll tell you what the actual origin is, and we'll see some scenes based on something that we have said or done.

[E]

Take down a peg. That's what Jon Hamm did to that woman in an elevator, right?

[D]

Yeah. Where peg was like, hey, da, da, da. And he.

[A]

I want to be an adwoman.

[E]

I don't think about you at all.

[D]

Think about you.

[E]

I wonder if Mad Men. I wonder if it's ready for a rewatch on the old Mad Men. Have I. Have I forgotten enough about Mad Men that I could enjoy watching it again? Will it be all new to me at this point?

[D]

I think so.

[E]

Adam is just going through thousands of cards in his hand, and it's like, slightly off camera for him. But I was just. That whole time we were talking, he was just, like, leafing through so many cards.

[D]

Well, here's the thing. I got excited because Take Someone Down a Peg is on.

[E]

Is on there.

[D]

Yes. So we're going to start with. And I was like, ooh, I think it's in here somewhere.

[E]

And I found I get to do my Mad Men joke twice this episode.

[D]

So we're going to start with take someone down a peg. Where do we think that comes from? What incident do we think led to this ubiquitous phrase.

[E]

When you're going down on someone while they're pegging you? That would be.

[D]

Well, NBC just fined us $25,000. We have to fire. I want to say. What's her name? Who invented Marcel the Shell?

[E]

Jenny Slate.

[D]

Jenny Slate. We have to fire Jenny Slate.

[A]

It's like not going down a ladder, but going down. It's a literal peg in the wall that you're moving down.

[E]

Oh, interesting.

[A]

I don't know.

[E]

Yeah, going down a peg to take down a peg. Peg leg. My mind goes to Pirate Ship. It's gotta be something about, like, descending a pirate ship. Like, Adol's shaking his head. Like, anything I'm saying makes fucking sense at all. Which is crazy.

[D]

It has something to do with ships and flags. So you're definitely on the right track with Pirate Ship and pegs.

[A]

Taking down a.

[E]

Did the flags have a peg system? I don't understand.

[D]

So 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.

[E]

Oh, I'd like to see. How early are we talking? Like 6:00am yeah, probably 6:00amAdol, you are.

[A]

A ship's captain and you are doing, like, you're talking to your whole crew about the order that you're ranking everyone in. And it sort of feels like MySpace, like, top eight. Like, it's very catty and really emotionally intense.

[E]

H.

[D]

Okay, gather round, gather round. All right, let's see. Welcome to the first day on the ship. Of course, what we do is.

[A]

You look so handsome today.

[D]

Oh, Becky, thank you so much. Becky, you're co captain. Let's say you're one of my top five.

[A]

Oh, my God, thank you so much.

[D]

Yeah. So move over to the left here. Let's see who else? Who else?

[E]

Four other co captains. Guys, that could be any one of us.

[D]

All right, we're looking for. All right, you there, what's your Name?

[E]

Oh, me? I'm Jeff. I'm brand new to the ship.

[D]

Oh, brand new. Yes, you do have a brand there. That's my brand. Of course. Blackbeard's brand. Big beard. Did it hurt?

[E]

I'm also drinking a Blackbeard's brandy, which is, by the way, delicious.

[A]

Did it hurt when you fell from heaven, sir?

[D]

Oh, what's her name?

[A]

Oh, my God, I forgot my name. Oh, my God.

[E]

Toss him overboard.

[A]

Toss him overboard. My name is. Toss him.

[D]

Toss them. Just in the nick of time. You're gonna go ahead and move over here. You're going to my co captains.

[A]

Oh, my God.

[D]

Thank you so much, whoever I was talking to earlier. You go ahead and jump off the ship, kill yourself.

[E]

Okay, we're on land, so that'll definitely kill me. No, haven't really launched the ship yet. Okay, maybe can I go off the other side? No, no, no. Water side. Yeah, smart.

[D]

Bye. Bye.

[E]

Good captain.

[D]

Okay, now I'm looking for a bestie. Someone who, you know, you were only.

[A]

Like 4ft off the ground. He sort of fell, ducked, and rolled and kept running.

[D]

Huh? Go ahead and hand me my gun.

[A]

There you go.

[D]

And let me close one eye. And bam.

[A]

Oop. Shot back into your shoulder.

[E]

Definitely don't close your eye while you're shooting your gun.

[D]

But I only have one to spare.

[E]

Adol. Aaron, I am in the dumps.

[D]

Oh, why you sad? What's going on?

[E]

No, I was trying to buy a lemon, but it turns out I was haggling with this guy trying to buy this lemon. I wanted to, you know, make my water a little more refreshing. And eventually I got home with the thing, and the guy sold me a bad car.

[D]

Yeah, lemons can be bad cars.

[E]

Well, I didn't know that.

[D]

Have you heard? Have you used car gurus?

[E]

Oh, Cargurus. I know Cargurus. It's car shopping made for you.

[A]

Mm. With Cargurus Discover, you can skip the filters and describe what you're looking for in your own words. Simply type what you want, and Cargurus Discover instantly services real listings and match you with your exact needs so you don't end up with a lemon.

[D]

With more than 4 million listings, CarGurus has the biggest selection of cars, so it's easier than ever to find the right car and the right deal.

[E]

Okay, let me just use it real quick. I'm going to type into yellow exterior, citrusy. Lots of seeds inside. Oh, okay. Well, this is great, because with Cargurus, you can compare cars side by side, check pricing, and estimate your Final cost so you can navigate the dealership with with confidence.

[A]

It's no wonder Cargurus is the number one most visited car shopping site according to similarwebs estimated traffic data.

[D]

But don't take it from them. Take it from me. Honk. Honk. A real car. Buy or sell your Put the brakes on, sweetie.

[A]

Sorry.

[D]

Buy or sell your next car today with [e-mail] Go to CarGurus.com to make sure your big deal is the best deal. That's C A r G u r u s.com cargurus.com Hong Kong get in everyone.

[A]

Honk, honk.

[D]

We're going to the moon.

[E]

Hey. Smells like lemon.

[A]

Adel jpc. You may have noticed my new diamond and emerald necklace. I bought it with the money I saved using rocket money.

[E]

Whoa.

[A]

Mm. I realized I was spending like $800 a year on unwanted apps and subscriptions. And then turns out I don't need to do that. Rocket Money canceled them for me.

[E]

Okay, Aaron, but this. I mean, this necklace looks really expensive.

[A]

Rocket Money is a personal finance app that helps find and cancel your unwanted subscriptions, monitors your spending, and helps lower your bills so you can grow your savings.

[E]

Okay, I'm seeing a receipt. Adeline, the trash can't hear. I don't think Eric wants grab your hand. She spent a lot. She spent a lot on this necklace.

[A]

The app consolidates checking, savings, loans, and investments into a single dashboard to give a user a clear view of their financial picture. I've been using Rocket Money for years, way before they were ever a sponsor of hey Riddle. Riddle. And I love how clear their communication is. If there's a big spend on my card, it will let me know right away. And it will also let me know what upcoming bills I have to pay. And I'll even negotiate lower bills for you. What a dream.

[D]

And for someone like me who hemorrhages money, Rocket Money can help set budgets and goals. I get personalized insights and regular reports. And I can receive real time alerts for large transactions, upcoming bills, refunds, and low balances.

[E]

Yes, I'm looking at Erin's Rocket Money right now and she has a goal for a new diamond necklace. Aaron, this is too many zeros. Aaron, this is too many zeros.

[A]

It's like 18 zeros. What's wrong?

[E]

Well, let Rocket Money help you reach your financial goals faster. Join RocketMoney.com Riddle that's RocketMoney.com Riddle RocketMoney.com.

[A]

Riddle I have to be honest with you guys. This Is not a real diamond necklace. It's a bunch of bugs I convinced to be in a diamond formation. Still costs $100,000.

[D]

Pretty good. What about the phrase the full Monty?

[E]

Damn, I feel like we were just talking about that too.

[D]

Just talking about the full Monty that.

[E]

Is showing someone your Pendis, I believe.

[A]

Pendis. Pemdas.

[E]

Pemdash. But where would it come from?

[D]

Now this is a tough one because it's very specific.

[E]

Monty seems British, right? Monty seems like the UK.

[D]

This phrase originates from early 20th century England.

[E]

Okay, okay. But do we. Is like, is there a maybe like a British celebrity that was named Monty or something?

[D]

Now, there was a tailor in early 20th century England that this phrase stems from. What do we think Monty is short for?

[E]

Montague.

[D]

A tailor named Sir Montague Burton started using the term full Monty for his three piece suits.

[A]

Why then what have we done to that man's work?

[E]

He was saying the full Monty is a three piece suit that's all been tailored by him.

[A]

Yes. I'd like to see a scene. The three of us are all in heaven and jpc, you are Montague the tailor. And we kind of pity you that your. Your legacy on earth has turned into something it wasn't supposed to. More wine? More wine?

[D]

Yes.

[E]

Yeah, I'm in this. I'm honestly gonna need it. Yeah.

[B]

Oh, why?

[D]

What's.

[A]

Yeah, Monty bothers you? Dc, why the long face?

[E]

It's nice of you guys to do this. It's nice of you guys to kind of pretend that you don't know what's going on, but obviously you. Most of my name has kind of been. No, it's rolled through the mud down there.

[B]

What?

[E]

Yeah. You heard about that? Yeah. Oh, yeah, I heard about that. Yeah. I. Whoa. Man, I really thought it was gonna be about nice suits. You know, it's just like, I'm not mad, but I'm just like part of me. I was like. I was so close. I was. Because in life it was really about the nice suits.

[D]

Sure, sure, it was.

[E]

Now it's like flashers and kind of like male exotic dancers. Thunder from Down Under. You know, that kind of stuff. Oh, you.

[D]

You know, specific ones. Yeah.

[A]

I mean, are you taking a peek at Thunder down from Down Under? Wait, you're covered in glitter.

[E]

Oh, this? No. Yeah, I was. Have I gone to Thunder from down under today?

[B]

Have I?

[E]

1, 2, 3, 4. Hate riddle riddles. Clue crew, listen to the rest of the episode now by starting your free 7 day trial at patreon.com heyriddle riddle.