Patreon Preview #386: The Prestonshire Country Club w/ Damon Royster

Summary

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Episode Overview

Episode Title: Patreon Preview #386: The Prestonshire Country Club w/ Damon Royster
Podcast: Hey Riddle Riddle (Headgum)
Release Date: July 31, 2026
Guests: Damon Royster

This Patreon preview features a satirical and absurd improv adventure at the fictional Prestonshire Country Club, with the gang (Adal Rifai, Erin Keif, JPC/John Patrick Coan, plus guest Damon Royster) taking on various eccentric roles: bumbling security guards, a new nervous server, multiple Bradleys (including famous Bradley Whitfords), and many caricatured country club elites. The episode lampoons exclusivity, class, and the bizarre rituals of the upper crust—all with the hosts’ trademark surreal riffing, shifting identities, and running gags about slaps, privilege, and "Grindr for dogs."

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Key Discussion Points & Segment Highlights

1. The Country Club Entrance Gauntlet

(00:33–05:48)

• Setting the Scene: Guest "Bradley Whitford" (adopted persona) tries to navigate Prestonshire’s absurd security and tangled social hierarchy to gain entrance.
• Security’s Absurd Standards:
  • Security guard Dave quizzes for membership status—having “47 Bradleys” in the club, needing to clarify which is which.
  • Notable quotes:
    • "That’s one of the big Bradleys. One of the top three Bradleys." (Country Club Security/Dave, 01:32)
• Confusion Over Celebrity Identity:
  • Whether “Bradley Whitford from West Wing or Billy Madison” is admitted; running joke about famous actor confusion plus Margo Martindale/Ann Dowd mix-ups.
• Comically Difficult Admission:
  • Reference to non-college grads prompts security to attempt ejecting the guest.
  • "I didn't—I’m not a college graduate myself." (Bradley Whitford, 02:46)
• Mock Tech Credentials:
  • “Applicant” claims he created “Grindr for dogs,” setting up future bits about investor interest and canine matchmaking.

2. Meet the Odd Cast of Members

(05:48–09:58)

• Parade of Bradleys:
  • Multiple faux-Bradleys (from Get Out, West Wing) interact with security—parodying celebrity status and in-group favoritism.
• Excluded Bradleys:
  • “Bradley Whitford from Get Out” is barred entry due to club board’s ruling, delivering a meta-joke about persona non grata status:
    • "Until the board decides, you are hereby banned from the Prestonshire Country Club." (Country Club Security/Dave, 05:53)
• Sudden Sponsor Transition (Skip):
  • Brief sponsor plug included—no content value.

3. Training the New Server—Hellish Hospitality

(09:58–13:41)

• Marty’s First Day on the Job:
  • Damon Royster’s “Marty” (the new, nervous server) is introduced and receives bleak, darkly comic advice from veteran staff—hide all humanity, expect abuse.
  • Notable Exchange:
    • "Try not to show any human side of yourself." (Aaron, 11:21)
    • "My face is soft." (Aaron, 11:14)
    • “If you can hold a golf club, you can use this country club.” (Bradley Whitford, 12:05)
• Wealthy Teens:
  • Joke about 18-year-old members and their “less painful” slaps juxtaposed with sharper verbal barbs.
• Marty’s Naivety:
  • Marty expresses hope to “charm with an open heart”—laughed down by all, reinforcing the club’s cutthroat climate.
  • "That's a terrible thing to tell a child." (Bradley Whitford, 12:49, on Marty's prior job as a children's performer)

4. When the Staff Revolts: A Brief Uprising

(13:41–14:58)

• Marty’s Breakdown and Call for Humanity:
  • Marty, pushed to the limit, jumps onto a table and loudly asserts their humanity before the horrified elite.
  • "I am not just your server. I am a human being. I have lived, I have loved. I've cried." (Marty, 13:47)
• Elite Response:
  • The guests panic, calling for Marty to be “killed with fire,” lampooning the dehumanization of service workers.
• System Restoration:
  • Marty is heroically rescued by another staffer, only for the hierarchy to snap back to normal—“the system is alive and well.”
  • “Equality between all of the different socioeconomic people in this country does not exist. Go back to your meals.” (Aaron, 14:35)

5. Surreal Denouement: Memory Wipe and Reset

(14:58–15:19)

• ‘Men in Black’ Moment:
  • Sudden “memory wipe” – a group in suits erases everyone’s memories, everything returning to business as usual—deft commentary on institutional inertia.
  • "What was I doing? Buy. Sell." (Country Club Security/Dave, 15:04)

6. Preview, Close, and Meta Outro

(15:19–16:15)

• Subscription Promotion:
  • Seconds-long snippet urging listeners to join Patreon to hear the rest.
• Mock Podcast Plug:
  • Satirical ad for a fictional new pod, "What's Our Podcast?", riffing on indecisiveness and featuring fake big-name guests.

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Notable Quotes & Moments

| Timestamp | Speaker | Quote/Paraphrase | |-----------|---------|----------------------------------------------------------------------------------| | 01:32 | Security/Dave | "You should get to know him. That's one of the big Bradleys. One of the top three Bradleys." | | 02:46 | Bradley Whitford | "I didn't—I’m not a college graduate myself." | | 05:53 | Security/Dave | "Until the board decides, you are hereby banned from the Prestonshire Country Club." | | 11:21 | Aaron | "Try not to show any human side of yourself." | | 12:05 | Bradley Whitford | “If you can hold a golf club, you can use this country club.” | | 12:49 | Bradley Whitford | "That's a terrible thing to tell a child." | | 13:47 | Marty (Damon Royster) | "I am not just your server. I am a human being. I have lived, I have loved. I've cried." | | 14:35 | Aaron | "Equality between all of the different socioeconomic people in this country does not exist. Go back to your meals." | | 15:04 | Security/Dave | "What was I doing? Buy. Sell." |

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Tone and Style

The episode is powered by lightning-quick, absurdist improv with an acerbic, satirical edge. The tone is irreverent and self-aware, lampooning both elite culture and the improv genre itself. Characters speak in rapid succession, often doubling down on running jokes about class, celebrity, and the dehumanization of service workers. Interactions are laced with playful cruelty, deadpan declarations, and surreal "left turn" moments (like the Men in Black memory wipe) true to the podcast’s style.

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For Listeners Who Missed It

This episode is a fast-moving, laugh-packed sendup of country club exclusivity and service industry indignities. Through a kaleidoscope of characters, role-switching, and increasingly wild scenarios, the Hey Riddle Riddle crew and Damon Royster parody privilege, identity confusion, and the farcical lengths people go to maintain their place in rigid social systems. Richly quotable, packed with running gags (“the big Bradleys,” “Grindr for dogs,” “never show your humanity”), and never letting up, it delivers exactly the blend of chaos and comedy usual subscribers expect.

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Note:
Timestamps included highlight where in the episode to find key exchanges; ad reads and meta outros are omitted from content analysis.

Transcript

[Adol]

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[Country Club Security (Dave)]

Hey, how you doing today, sir?

[Bradley Whitford (Guest)]

Oh, I'm fine. I'm sorry, I'm just. I'm trying to get to the. Is this the Prestonshire Country Club?

[Country Club Security (Dave)]

Yeah, I'm Dave. Can I see your membership card, please?

[Bradley Whitford (Guest)]

Oh, no, I don't have a member. Oh, I have a guest. I have a guest.

[Marty (New Server)]

Pass.

[Bradley Whitford (Guest)]

I'm meeting a member.

[JPC]

I'm meeting.

[Country Club Security (Dave)]

I'm having a. Oh, okay. Just who you mean. I'll check the list here.

[Bradley Whitford (Guest)]

Bradley.

[Country Club Security (Dave)]

Oh, I gotta tell you, we got 47 Bradleys.

[Bradley Whitford (Guest)]

Oh, I'm sorry, I thought. I didn't know if you would. I didn't know if I should wait for you to look up the Bradleys and then I would give the last name or just. You want the full.

[Country Club Security (Dave)]

It's all in my head. I don't need to look it up. I mean, here at the Preston Shire Country Club, we take our job seriously.

[Marty (New Server)]

Excuse me. Bradley Bradlerson.

[Country Club Security (Dave)]

Oh, go right through, sir. Yes, very good, sir.

[Marty (New Server)]

Thank you so much.

[Bradley Whitford (Guest)]

Oh, okay. Oh, so that's.

[Country Club Security (Dave)]

That your friend?

[Bradley Whitford (Guest)]

No, that's. I don't. I don't know that man.

[Country Club Security (Dave)]

You should get to know him. That's one of the big Bradleys. One of the top three Bradleys.

[Bradley Whitford (Guest)]

That's kind of something that I was, like, looking forward to doing while I was here, is like networking, you know, with like.

[Country Club Security (Dave)]

Oh, yes.

[Bradley Whitford (Guest)]

Not that. You know, not that, my friend. It's Bradley Whitford.

[Country Club Security (Dave)]

Okay, we have three Bradley Whitfords. Is this the one from the West Wing or the one from Billy Madison?

[Bradley Whitford (Guest)]

Yes, it's Billy Madison. Yes.

[Country Club Security (Dave)]

Okay. And here's the thing. People confuse them all the time.

[Bradley Whitford (Guest)]

I know. Yeah. It's like a Margo Martindale, Ann dowd situation.

[Country Club Security (Dave)]

Absolutely.

[Aaron]

Dr. Bradley Bradson.

[Country Club Security (Dave)]

Yeah. Going through.

[Aaron]

Hey, thanks. And by the way, a bird shit on my car last time I was here. Can you do something about that?

[Country Club Security (Dave)]

It's one of the worst Bradleys. Dr. Bradley is one of the worst Bradleys. He's had me Kill so many birds.

[Bradley Whitford (Guest)]

Oh, killed birds. I thought you said, he's had me killed. And I said, oh. Oh, God. Oh, God. No, but he's had you kill birds.

[Country Club Security (Dave)]

No, I wouldn't be here if I had been killed. Surprised you. Where'd you go to college? Oh, Princeton or Brown.

[Bradley Whitford (Guest)]

Is this gonna. I didn't. I'm not a college graduate myself.

[Country Club Security (Dave)]

Okay. Presses the button, press.

[Bradley Whitford (Guest)]

Oh, no, no, no, no, no, no. But, but, but, but. I, I, I, I work in tech.

[Aaron]

A couple people run out and start dragging his car backwards.

[Bradley Whitford (Guest)]

No, I work in tech. I work in tech. Wait, wait, wait. I work in tech.

[Country Club Security (Dave)]

Oh, hold on.

[Bradley Whitford (Guest)]

I. Am I.

[Country Club Security (Dave)]

Okay, short for application or short for appetizer?

[Bradley Whitford (Guest)]

Which one is more impressive?

[Country Club Security (Dave)]

Well, they both have their wins and their losses.

[Bradley Whitford (Guest)]

Application. I develop applications.

[Country Club Security (Dave)]

Okay. Which one?

[Bradley Whitford (Guest)]

Have you heard of Grindr?

[Country Club Security (Dave)]

I haven't just heard of it. I'm also a user.

[Bradley Whitford (Guest)]

I don't know. I'm not.

[Aaron]

It's us, the Brad. Brad twins.

[Marty (New Server)]

I'm Brad and I am also Brad.

[Aaron]

Let us through.

[Country Club Security (Dave)]

Go on in. Go on in. Thanks, guys. Thanks, guys.

[Bradley Whitford (Guest)]

No problem.

[Marty (New Server)]

Wait, did I hear Grindr come up?

[Bradley Whitford (Guest)]

I. I'm sorry, I.

[Aaron]

He's the gay twin.

[Bradley Whitford (Guest)]

There's always one. I was using that as an example. I don't. I did not invent Grindr. Didn't work on Grindr, but I was like, have you heard of Grindr? I have an app that is basically Grindr for dogs.

[Marty (New Server)]

Oh, well, we also have two gay

[Adol]

dogs,

[Aaron]

and we love to invest money in things.

[Bradley Whitford (Guest)]

Oh, my God. This is exactly why I wanted to be here.

[Aaron]

Well, we'll see you inside. They're two different cars. Somehow

[Country Club Security (Dave)]

I wish. People come up here in the fanciest cars and they go from 0 to 120 down the. I mean, I just wish. Yeah, they'd slow down, but it's their place. It's their place.

[Bradley Whitford (Guest)]

Yeah. It's their place. So, yeah, I mean, I. Part of what I'm looking for is to get investors interested in Grinder for dogs.

[Country Club Security (Dave)]

Okay.

[Bradley Whitford (Guest)]

We don't even have a name yet.

[Country Club Security (Dave)]

Okay, Just call it. Ask what it's called.

[Bradley Whitford (Guest)]

Yeah, I mean, I don't know. Do you have any suggestions? Like, that's what. That's kind of what I'm. Bradley Whitford wanted me to be here for.

[Country Club Security (Dave)]

You know, just to get poor doggy styles. That's no good. I mean, there's a reason I'm security and not, you know, name.

[JPC]

Doggy style's not so good, huh?

[Bradley Whitford (Guest)]

I've never I've never heard someone say that.

[Aaron]

Hey, it's Bradley Whitford from West Wing. Diana, Can I get through?

[Country Club Security (Dave)]

Yes, go on. Go on through. Let me walk and drive with you here. Let me just.

[Aaron]

The President needs something on his desk by tomorrow or something.

[Country Club Security (Dave)]

Absolutely. And let me just say, those pants are tremendous.

[Aaron]

Thank you. They're baggy and my shirt's baggy and I got a 90s tie.

[Country Club Security (Dave)]

90s tie. Mikhail Gorbachev. Something witty.

[Bradley Whitford (Guest)]

Oh, I gotta get in there. I gotta get in there. I mean, these are the people, these are the Bradleys that I'm here to meet. Please.

[Marty (New Server)]

Beep beep beep. It's me, Bradley Whitford from Get Out. Can I get in now?

[Country Club Security (Dave)]

Bradley Whitford from Get Out. I've told you, you are no longer welcome.

[Marty (New Server)]

It was just a character I played in a movie. Come on.

[Country Club Security (Dave)]

Until the board decides, you are hereby banned from the Prestonshire Country Club. Inherited, never earned. Hey everybody, Adol here. Don't panic. I'm trying not to. The three of us were at the Cook County Pie factory. I'm still here on a self guided tour of course. And JPC and Aaron leaned over a bit too far and fell into the pie vat. So they've been baked into pies. I'm trying to run around eating through the pies to find them. No such luck so far. But I do want to let you know this is stressful, of course, but one of the most stressful things we have to deal with after a busy day of recording riddles is what are we going to have for dinner? JPC of course, always suggests. I've got a bone to pick with you and Aaron's all We should have a bottle of contrada. 45 minutes later, 2/3 of us are baked into pies. This all could have been avoided with Tempo. The meals are already prepared, ready in two minutes and make it a whole lot easier to eat fresh balanced meals during the week. With over 20 recipes every week. Made from nutrient rich ingredients, Tempo keeps things exciting and helps you stay consistent with healthy habits. And no matter your goals, there's a Tempo meal for you. Protein packed meals with over 30 grams of protein, fiber, rich calorie, conscious gut support and even glp. One smart meals Gulp. One I guess is maybe how you pronounce it. Personally, I've recently had some favorites from Tempo, including the Barbecue Pulled Pork sweet potato Skillet, the Fiesta Grilled chicken and rice and and the most fun to say, the lean and clean Rotini Bolognese with garlicky broccoli. Yum, yum, yum. For a limited time, Tempo is offering our listeners 60% off your first box. Go to tempomeals.com riddle that's tempomeals.com riddle for 60% off your first box. Tempomeals.com riddle rules and restrictions may apply. Oh, Oh, I bit into a pie. It's Aaron. Oh, nope, that's a blackbird. Hmm, Maybe Aaron. Oh, it is Aaron. You're free. She just flew out the window. Classic Aaron.

[Bradley Whitford (Guest)]

Hey, everybody.

[JPC]

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[Bradley Whitford (Guest)]

Okay, so these are the chafing dishes. You basically want to make sure that there's always some sort of pork, of course, on the table, you know, at any given time. So right now, since it's breakfast, it's going to be pork sausage, you know, but if Anyone eats all the pork sausage, have to make sure that there's

[JPC]

our members really like porn.

[Marty (New Server)]

Okay. I'm just, I'm so nervous. It's my first day working at a place that's fancy, you know.

[Bradley Whitford (Guest)]

Well, yeah, I mean, it's. I mean, look, I don't want to sugarcoat it for you, okay? It's pretty nerve wracking. And it's going to be nerve wracking. You know, I'm nervous and I've been here for 10 years. You know what I'm saying?

[Marty (New Server)]

Wow. Yeah.

[Bradley Whitford (Guest)]

Because not only could one wrong move get me fired, but it would ruin my life. Because the people here are vindictive and they're petty and they will go out of their way to fuck you over at every chance.

[Aaron]

Oh, guys, it's a pretty good day. So far I've only gotten slapped twice and spit at once. Oh, is this a new guy?

[Marty (New Server)]

Yes.

[Bradley Whitford (Guest)]

Michelle, this is Marty. Marty is new here. Michelle is one of our best at getting slapped.

[Marty (New Server)]

Wow. That. That's something I aspire to.

[Aaron]

I have a soft face.

[Adol]

It's the cheeks.

[Bradley Whitford (Guest)]

It's the cheeks. It's all in the cheeks.

[Marty (New Server)]

I was gonna say it looks like it's falling off of your skull. Your face.

[Aaron]

Well, Marty, a little bit of advice. Try not to show any human side of yourself.

[Bradley Whitford (Guest)]

Oh, good idea.

[Marty (New Server)]

Okay. I mean, that's hard. I used to be a children's performer, so. And that's all about just being vulnerable and sharing your feelings and also naming body parts.

[Bradley Whitford (Guest)]

Children and performer. Oh, Marty, don't say those two words anywhere in this. This is an 18 over country club. So no one here wants to be reminded of children and performers that come here. Oh, we have some very wealthy 18 year olds that come here.

[Marty (New Server)]

Wow.

[Bradley Whitford (Guest)]

Yeah. If you can hold a golf club, you could use this country club.

[Aaron]

I like them because their slaps don't hurt as much.

[Marty (New Server)]

No.

[Bradley Whitford (Guest)]

But their verbal barbs hurt even more.

[Aaron]

True.

[Bradley Whitford (Guest)]

Isn't that fun?

[Marty (New Server)]

I don't know, guys. I know you have this decade of experience, but I think I'm gonna really charm these people with my open heart and my kind spirit and my soft voice.

[Aaron]

Woof. Good luck, Marty. I'll see you out there.

[Bradley Whitford (Guest)]

Yeah.

[Marty (New Server)]

Okay.

[Aaron]

I walk out and someone immediately backhands me across the face as I'm walking with the tray.

[Bradley Whitford (Guest)]

You might also want to clear out your locker, Marty, before you go out, because I don't think with that attitude you're going to be lasting here very long.

[Marty (New Server)]

Well, you know, as I told Susie, age 8, anything can happen.

[Bradley Whitford (Guest)]

It's a terrible thing to tell a child. Hi.

[Marty (New Server)]

Good morning. I'm Marty. I will be your server today.

[Country Club Security (Dave)]

Yes.

[Aaron]

Very good.

[Country Club Security (Dave)]

My name is Theodore Sterling of the Rhode Island Sterlings. I'll start with the prime rib, then have the flaminion, and then for dessert, more prime rib.

[Marty (New Server)]

All right, so that's prime rib.

[Country Club Security (Dave)]

Flaminion slaps you in the face with the menu,

[Marty (New Server)]

Sir. I didn't like that.

[Bradley Whitford (Guest)]

What the hell? They can speak.

[Marty (New Server)]

Sorry, everyone.

[Aaron]

They could speak. They could speak.

[Country Club Security (Dave)]

Unbelievable.

[Bradley Whitford (Guest)]

They could talk. Oh, my God. Kill it. Kill it with fire. Fire is the only way. Yes. Fire. Bring fire. Kill it with fire.

[Marty (New Server)]

No. Let me live.

[Country Club Security (Dave)]

It can have opinions because it's opinionated emotions.

[Marty (New Server)]

Jump onto a table, everyone. I am not just your server. I am a human being. I have lived, I have loved. I've cried.

[JPC]

You.

[Bradley Whitford (Guest)]

Impossible.

[Aaron]

Uh, no, I'm sorry. That can't be right. Cause I'm a human being, and we are certainly not the same kind of thing.

[Marty (New Server)]

This woman is drunk. But equals.

[Country Club Security (Dave)]

We're all drunk.

[Bradley Whitford (Guest)]

Every woman here is drunk.

[Country Club Security (Dave)]

Eloise, shut up.

[Marty (New Server)]

Don't you see? We're all just people in various stages of sobriety. That's all this is.

[Country Club Security (Dave)]

Various stages. Like a cast system. Yes.

[Aaron]

No, no, no. I come in, I knock him over the head, I pull Marty out. No. The system was just as it was before. Their hierarchy is alive and well. Equality between all of the different socioeconomic people in this country does not exist. Go back to your meals. We're so sorry.

[Country Club Security (Dave)]

People in suits rush in and sort of Men in black, everyone. And indicting. Hey, what was. What was I doing? Buy. Sell.

[Aaron]

Buy.

[Country Club Security (Dave)]

Sell.

[Bradley Whitford (Guest)]

Yes. Burn with fire. Sell fire. Sale. Sell my stocks.

[Marty (New Server)]

Could you put diamonds in my iced tea?

[Aaron]

Oh, yes. Right away, sir.

[Country Club Security (Dave)]

It spoke. It spoke.

[Bradley Whitford (Guest)]

1, 2, 3, 4.

[Kyle Mooney]

Hate riddle.

[JPC]

Riddles.

[Bradley Whitford (Guest)]

Clue Crew, listen to the rest of the episode now by starting your free seven day trial at patreon.com heyriddle Riddle. What's up, everybody?

[Kyle Mooney]

I'm Kyle Mooney.

[Bradley Whitford (Guest)]

And what's up, everybody?

[Kyle Mooney]

I'm back by and man. Ooh, we got something to tell you.

[Bradley Whitford (Guest)]

Oh, yeah, we definitely do. Yes.

[Kyle Mooney]

It's a brand new podcast on Headgum.

[Marty (New Server)]

That's right.

[Bradley Whitford (Guest)]

And it's called what's our Podcast?

[Kyle Mooney]

Yep. And that's because we don't have a single idea what our podcast should be about.

[Bradley Whitford (Guest)]

Yeah, we don't. So we actually have guests come on and they tell us what they think our podcast should be about, and then we try it. Yep.

[Kyle Mooney]

Guests like Mark Marin, Jack Black, Brittany Broski, Kate Berlant, Bobby Moynihan, Meg Stalter. And Tim B. Landon axler.

[JPC]

Joan.

[Bradley Whitford (Guest)]

Joanie McGre.

[Kyle Mooney]

And Dender.

[Bradley Whitford (Guest)]

And Dender. New episodes release every Wednesday, so subscribe

[Kyle Mooney]

to what's our podcast on YouTube or any of your favorite podcast platforms. Yeah, I'm gonna go do it right now.