Loading summary
Aaron
This is a Headgun podcast.
Adeline
You're listening to this podcast, so I know you've got a curious mind. Here's a helpful fact you might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to progressive.com, answer some questions and you'll get a quick quote with discounts that are easy to come by. In fact, 99% of their auto customers earn at least one discount. Visit progressive.com and see if you can enjoy a little cash back. Progressive Casualty Insurance Company and affiliates. National average 12 month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary.
Casey
Great. You guys are all good. Have fun. Thank you, Kasey.
JPC
Thank you. Casey, we love you.
Casey
We love you, Casey.
Josh Gondelman
We love you, Casey.
Casey
You have fun.
Aaron
Casey too.
Casey
You have fun.
Aaron
He didn't say it back. It was a heart. That's not the same thing.
JPC
He never does.
Casey
I really like you guys so much.
Aaron
Terrible.
Josh Gondelman
Sounds like we're more into Casey than Casey's into us.
JPC
Exactly what it sounds like.
Casey
Slams the door in our face. Okay. We walked him home for nothing.
Aaron
Not even a nightcap. Unbelievable.
JPC
He stood on a block of ice. Both of them were goldfish. It was the cat addon of an airplane. He dabbed him with an ice.
Aaron
Adel, your lawn is looking fantastic.
Casey
Oh, thank you. Thank you. Yeah, I decided to kind of care this year about my curb appeal.
Aaron
It looks great. JPC is my neighbor on the other side and he's doing all sorts of stuff that I feel like the HOA is not going to be too happy about.
Casey
Yeah, yeah, I have, you know, obviously I have my 100 foot skeleton up year round, which I love the summer
Aaron
sun hat on him. He looks dashing.
Casey
Yeah, Etsy has so many fun ways to dress up your hundred foot.
JPC
You guys talk about lawns?
Casey
Oh, hey, neighbor.
Aaron
Hi, tpc.
JPC
You like my gasoline lawn?
Casey
Yeah, the smell is interesting.
JPC
It's. Yeah. You got a good nose on you. That's straight gasoline, my friend.
Aaron
Yeah. I wonder if, like the fire pit in the middle of it is wise.
JPC
Interesting. I wouldn't know if a fire pit could be wise. You know, Dangerous, yes, but wise. Not really the quality I would imbue with a fire pit.
Casey
But can I ask about the sort of American ninja course for raccoons you have going on? Well, a lot of them are drowning.
JPC
I'm glad you brought that up.
Aaron
I'd say most, if not all of them are Drowning.
JPC
This is not for American raccoons. They're too clever for me. I have to import these raccoons.
Aaron
Did you know that the raccoon warrior
JPC
is the only North American marsupial?
Aaron
That's not true.
Casey
Aren't possums.
Adeline
Huh?
Casey
Aren't possums. Jpc. Aren't possums.
JPC
Aren't possums.
Adeline
Jpc.
JPC
Well, you and my wife have a very similar excuse.
Aaron
Well, have a good one. Oh, my God.
Casey
Well, we'll see you Adol.
Aaron
Please tell me you have a better neighbor on the other side of you.
Casey
It's actually cpj. Sort of a. Sort of an inverse jpc I don't have.
JPC
I got Josh Gondelman on my side, though.
Casey
Aw, lucky. God damn it. Hey, Josh. Josh Guidelman.
Josh Gondelman
Hey, guys. How's it going?
Casey
Good. Oh, my gosh. Would you. Damn it, Aaron. We gotta get him to move on the side of one of our houses.
JPC
Yeah.
Casey
Josh, are you willing to move?
Josh Gondelman
Yeah, I love to move. I like to move it. I love to move it. I'm willing to move it.
Aaron
JPC is going to make him run his raccoon course before he gets to the side of the street, though.
Josh Gondelman
I was just thinking, jpc, that's so many dead raccoons. I can't keep up with that. I can't compete.
JPC
Yeah, neither could they. That's kind of the whole problem. Lazy bastards.
Aaron
Oh, man.
JPC
Welcome to hey Riddle Riddle, everybody. This is the podcast where we do riddles. As always, our guest is Josh Gondelman. Josh, this is your second, third, third or third?
Josh Gondelman
I think my third riddle. Yeah.
JPC
Wow.
Josh Gondelman
First riddle. Crushed.
Aaron
Josh, it's always such a pleasure to have you here, and it's also such a pleasure to know you and to run out into you in the world. I'm trying not to be hyperbolic here, but you might be the nicest person I've met doing comedy besides Adeline.
Josh Gondelman
Jpc, that's really kind. I feel the same way. We had such a good time on that boat.
Aaron
We did. We did a Joco cruise together. And then, Josh, I did want to talk to you about something that we talked about at San Francisco Sketchfest this year.
JPC
Is this a performance review?
Aaron
This? A little bit. Josh let me was talking about his day. I think we saw each other on a Saturday night.
JPC
Okay.
Aaron
And kind of in the middle of your day, I guess it was early evening, you, in between your tasks, went to karaoke.
Josh Gondelman
Oh, yeah. Whoa.
Aaron
Yes. I've never heard anything like it. It kind of broke my brain. I didn't realize that you could sort of just drop into karaoke as an in between thing we did.
Josh Gondelman
So. So I was in San Francisco at Sketchfest, which I love, running, co hosting our regular semi regular show, Sup, bro? With my friend Alison Leiby, who. Her book just came out. She's a genius. Great friend, great writer and comedian. And we had dinner, and dinner ended so fast. We went to this place that's totally fine, but the previous year they'd given us a hummus plate where all the veggies were shaped like a human face on the hummus. And we were like, let's see if they do that again. And they did not.
JPC
Oh, yeah, that's weird. Guy has been fired.
Josh Gondelman
When they put it down, the waiter went, we don't usually do this. Like, he was confused by why it happened.
Casey
Sending a message.
Josh Gondelman
Yeah. He's like, you should have more. You should look like this. And so they gave us normal hummus. And then we ate really fast. And then we're like, we have like one hour where we can't really do anything. So we were like, we hadn't had anything to drink, and there was a karaoke place right across the street from the hotel. So we're like, let's just go for an hour and rip it. And the two of us went to do that. That was the mission. And outside the karaoke spot, we ran into Paul Saborin of Paul and Storm and of Joco Cruz. And he had never met Allison before. I was delighted to introduce them. And then we're like, well, we're going to do karaoke for one hour. Would you like to join us? And he was like, sure. And he's a professional musical comedian. So Alison and I were just like, bellowing. And Paul was like, doing his best, like. Like to kind of keep us on pitch. We did one hour of extremely aggressive, extremely sober karaoke and then went out and did our show.
Aaron
I was aghast. It's like someone telling me they ran a marathon in the middle of their day to kill time. I could not believe it.
Josh Gondelman
I'd never done a thing like that before. I think I know a few people that have that kind of as an entertainment habit of theirs where they'll go like, oh, we have a dinner reservation at 7. It's 5:30. We can just crush an hour of karaoke and try to feel our feelings before dinner. But this was my first time and it was awesome.
Casey
I gotta start thinking of when I can cram karaoke into my day. That's fun. Tuesday morning, 10am My mom was just over and she to stay with us for a couple days. And she had never done karaoke and she'd made a big to do of like, I've never done karaoke. I'd love to do it sometime. And so we have a karaoke machine in our basement. Brought it upstairs. She sang the Jardian song, which is her go to, and now it's crossed off her list.
JPC
What is the Giardian song?
Josh Gondelman
Yeah, I don't know what that song is.
Casey
I have type 2 diabetes, but I handle it. Well, it's a commercial. It's a commercial for a medicine.
Aaron
There was not a backing track for that. Right? She did it acapella. Please tell me there is not a backing track available for that online.
JPC
That's a preset on the machine.
Aaron
No, it's not.
Casey
But that's what my mom will sing to us for our birthdays now. Because like, three years ago. Exactly. But three years ago, she became obsessed with the song. And so we're like, instead of leaving a voicemail singing Happy Birthday at midnight every birthday, can you just sing that? And so that's her new thing. And we as a family love it.
Aaron
That's awesome. I guess being a mom can be fun.
Casey
Aaron, what were your hangups again?
Aaron
Mostly everything else.
JPC
Adam, who's the biggest celebrity you think you could conceivably get to sing that song for your mom? I mean, I'm assuming Amy Mann would take a turn at the Jardiniera song. What is it?
Josh Gondelman
When you said the Chicago Medicine, I assumed the Cleveland Guardians, the baseball team, had a theme song and you didn't know how they were pronounced. And I was like, that can't be right. Neither of those two things could possibly be true.
Casey
Well, Josh, I have a Jardiance of Ga' Hool tattoo, so I think I know how to pronounce jardiance.
Josh Gondelman
I thought it was Ja'. Hool.
Aaron
And Josh, I know we talked about this before, but what are some of your go to karaoke songs? Oh, gosh, the list that you gave me, I was like, that also sounds
Josh Gondelman
like it's a little chaotic. I've been doing. I've really settled into a groove lately with songs that nobody wants to hear. I've been doing Zoot Suit Riot by the Cherry Poppin. Daddy is a band name. I apologize for saying I do. Where you can find it. I'll do Dr. Worm by they Might Be Giants the best, which I love. Great song. It is like a song that if you are not in the right Room. People are like, that's not a song.
Casey
It's such a fun. They sang that on Joko 2 years ago last year. I'm obsessed with that song.
Josh Gondelman
It's such a good song. I'm trying to think of what else I used to do a lot more Springsteen. I love a Springsteen. Leiby and I will do Beer by Real Big Fish.
JPC
I love that song.
Josh Gondelman
Where we can find it? Yeah, it's fun as hell. So I kind of. It's like a little more ska centric than my normal music listening. But there's also, like. There's a genre, I think, of songs that are great karaoke songs and fine songs like Cryin by Aerosmith. I saw someone do it years ago and was like, oh, this is a great karaoke song. And, like, I never want to hear it not sung at karaoke. Yeah.
Aaron
Someone should make a playlist of that on Spotify. Bad songs, great at karaoke, and then
Josh Gondelman
another playlist of just people doing them. Karaoke is, like, proof of concept.
Aaron
Yes.
Casey
Switching from they Might Be Giants to Aerosmith gave me goosebumps, but I don't know if it's good or bad yet.
Aaron
It's definitely telling a story.
JPC
Yeah. The last time I did karaoke, I was kind of surprised that the place just had, like, YouTube pulled up and you just. You just use YouTube to find karaoke songs. I was like, oh, gone are the days of, like, the little machine that Adol has that, like, has the karaoke on it. It's all on the Internet now. Huh.
Josh Gondelman
The YouTube stuff is kind of nice because you can get some real deep cuts, really alienate the crowd. I've done, like, Aucarville river songs. Yeah. I'm trying to think of other. Because it is really fun. Maris really tore up some Ted, Leo and the pharmacists at a recent YouTube karaoke session. Yeah, really cool.
Aaron
JPC. You're still doing Gregorian chants every time you do karaoke.
JPC
My go to at karaoke is to pick a song where everyone's like, oh, hell yeah. That would be hilarious. But then, like, 10 seconds into it, people are like, wait, we don't want to do this. We don't want to sing this whole song.
Casey
The full six album.
JPC
Yeah.
Casey
Too many songs.
Josh Gondelman
You know what the greatest karaoke. I'm so sorry to interrupt.
Aaron
No, no, please.
Josh Gondelman
My friend Jaya Saxena innovated this, and it's closing the night with a full room performance of It's All Coming Back to Me now by Celine Dion.
Aaron
Brilliant.
Josh Gondelman
It's such a long song and and it's so dynamic. And you. I think if you are of a certain age, you, like, remember more of the words than you even think you do, for sure. And because she's such a good singer, you can't. Celine Dion. You end up like, I can kind of bring it down into my range in a way that works where I'm not like, oh, no, I have to do the Celine Dion thing. I'm just like the flesh and the f. Yeah.
Aaron
Everyone wants to grab their chest and go, baby, baby, baby.
Josh Gondelman
Feels so good.
Aaron
Oh, that's. And that's brilliant. That truly is the wisest thing I've heard in a long time.
JPC
And that's how Celine Dion gets to feel all the time.
Aaron
Oh, it must be so.
JPC
She could just do that at any
Josh Gondelman
time, but she couldn't for years.
Casey
Oh, yeah. Her.
JPC
That's right.
Casey
She had a condition.
Josh Gondelman
Yeah. It must feel so good to be like, I'm back and I'm Celine Dion.
Aaron
I like to do a duet at karaoke because I like to make eye contact with a friend while we panic about who's doing what. Harmony. And if we even remember the harmony.
Josh Gondelman
What is your. Do you have a go to duet?
Aaron
I Got yout Babe is so fun. People are always like, that's another one. People are like, oh, yeah, this is a good song.
Casey
Aaron, you and I did Summer Lovin', but you sang both parts. Yeah, I kept going, what the fuck?
Aaron
I kept putting my hand over your mouth and going,
Casey
just do the Wella Wellas.
Josh Gondelman
That song is like kind of four parts, right?
JPC
Yeah. Yeah.
Josh Gondelman
Because it's like the lead and then the two sets of background vocals.
JPC
I do Summer Lovin at karaoke, but it's with a friend in a different city doing their part in karaoke. And then I'm just doing my part.
Aaron
They're on speakerphone and it's delayed. That would be so funny.
JPC
I just explained to people the concept of the song is that someone is going to be doing the other part. Not here. That's how summer 11. I don't. I wish it worked differently.
Josh Gondelman
You only hear ever after half summer Loving Canonically.
Aaron
Are you there,
Josh Gondelman
Fun?
JPC
Oh, yeah. I'm dropping every other word. I'm not doing it like they do in the movie. I'm doing it like I'm going to a summer lover tunnel.
Josh Gondelman
There's like a. I don't think it's a problem to tell this story. We did, like, a Desus and Mera. When I worked for Jesus and Mera, we did, like, a staff Karaoke, which was so fun, everyone was just, like, going wild. But Ziwe did the entire Grease mega mix. Like, you would play it like a bar mitzvah or like a middle school dance. And she did the whole thing herself. And Maris, like, grabbed my arm and was like, she's a star to this day. We'll be like. That's how I knew she was a star when she did the whole Grease mega mix with, like 1 million percent commitment.
Casey
That rules.
Aaron
When I was in Greece, I played Jan. And So in summer 11, I had one line, and it's kind of the shortest, I'd say, worst line other than, did she put up a fight? Which no one likes saying. But I had how much dough did he spend? And I remember being in it, and if I didn't nail it, I'd be like, oh, well, I'll try again tomorrow night. You don't get a lot of chances in Grease if you're Jan. Brush and
Casey
brush and brush em, right?
Aaron
Yeah. They don't let you do the brush' em brush and brush em in the play. It's a movie thing. So they didn't let me do that.
Casey
I did step on. And I wanna call out the very good pun. Josh, would you please say it again?
Josh Gondelman
Oh, not a lot of janses.
Casey
Oh, take a chance on me.
Aaron
Not a lot of chances. Oh, yeah, I didn't get a lot of chances. That's true. Well, we're going to end the episode by singing that Celine beyond song. In the meantime,
Casey
have I told you guys My sister Saidiya is good friends with Jim Jacobs, who wrote Grease, and he put up. They Met through. He remounted an original production of Grease because it started in Chicago, went on to fame and acclaim, and then he brought it back to Chicago. And the original script is unbelievably dark.
Josh Gondelman
Really?
Casey
Yeah. They have, like, zip guns, whatever those are, which I think are just like little homemade guns or something. There's like a. How do I say this with any amount of class? There's like a ookie cookie situation. I think, like, there's just a lot of, like, really dark.
JPC
Wait a second. It feels like ooky cookie is dark.
Aaron
I can't do this.
JPC
I mean, hey, man, you don't love the game, we don't have to play, but dark.
Casey
You said that like Danny Zuko.
Josh Gondelman
I don't know if any. I bet at least one of the three of you has had this experience as a young person knowing about the movie Fast Times at Ridgemont High, thinking that it's Like a fun teen comedy. And then going, oh, no, because there's a lot of darkness in that movie as well.
Aaron
A tale as old as time. I think that we should do riddles.
JPC
Oh.
Aaron
So here we go.
Casey
Okay.
Josh Gondelman
See yourself.
Aaron
Okay, so this person has a last name, and they told me to have fun with their last name. And I don't know if that means they know I'm not going to be able to pronounce it or if I'm allowed to put my own little pizzazz on it.
JPC
Oh, is it pizzazz?
Casey
Have fun with it. Sounds like. Aaron, try and read it correctly. And then let's do another take and just have fun with it.
Aaron
Okay, great.
JPC
Yeah. Maybe throw one away. Aaron, we won't use it. We'll use it. It's the only one we'll use. Always.
Aaron
Wait, what was that?
Casey
We should say Jedi Patel is now directing our episodes.
Aaron
That's awesome. These are from Alex Demetrius.
Josh Gondelman
That didn't sound like fun. Yeah.
JPC
And Aaron, I gotta say, you barely made it through Alex. You said. You said Alex like it was like you were 100% confident.
Josh Gondelman
Was Alex spelled the normal way or
Aaron
is there kind of a funny. Yeah, it's spelled the normal way.
JPC
It's spelled back. It's backwards. It's X, E, L, A. And I'm like, alex, I guess.
Casey
Aaron, let's just.
JPC
Okay.
Aaron
Yeah, you're right. Shake it up, Shake it up.
Casey
And you're at karaoke. Aaron, you're at karaoke.
JPC
Aaron, do some vocal warmups.
Aaron
Yeah, baby, baby, baby. Okay, Yabiboo Bobby, put a pot pie
JPC
in Pooh Bear's Stomach by Be Ba Boo Boo.
Aaron
Okay, These are from Alex Demetris. I didn't have fun in that one either. These. I got it. This is easy. Actually, this type of stuff is really easy for me.
JPC
Classically, I think so.
Aaron
These are from Alex Demetrius. These are from Alex Demetrius. These riddles are from Alex Demetrius. No, that's probably offensive.
JPC
It sounded fun, Aaron. Hey, don't hide your light under a bushel basket. That sounded fun as hell.
Josh Gondelman
I wouldn't even stay under one of those things.
Aaron
Ridiculous expression.
Casey
Aaron, you were smiling. A lot of sweat got into your smile, but you were smiling.
Aaron
Oh, thank you.
JPC
Can I try one? Erin, can I try one?
Aaron
Yeah, of course.
JPC
These riddles are from Alex Demeter.
Aaron
You're having more fun than I am. And then your confidence on Alex helped. You're right.
JPC
Can I be honest with you?
Aaron
What?
JPC
I was not confident on Alex. I was like, I think I'm doing this.
Aaron
You seem so Confident.
JPC
No, it's just. It's fake. It's all false confidence.
Aaron
I'm gonna copy and paste this last name, and I don't. If you guys want to take a run at it.
Josh Gondelman
Yeah, I'm gonna take a stab. Any opportunity for fun.
Aaron
Yeah.
JPC
Oh, dermatologist.
Josh Gondelman
No, that was.
Casey
These riddles are from Alex Demitralis.
Aaron
Dimitrails trails. But doesn't it chemtrails?
JPC
Does this Demtrails this Emails from Alex Demeemtrails.
Aaron
Poor Alex is at their desk at work being like, this is the fucking weirdest day. No.
JPC
On Armor End.
Josh Gondelman
These riddles are from Alex Demetralis.
Aaron
Okay, I think we got a winner.
Casey
That's the one. We'll use Casey's.
JPC
I had a lot of fun.
Aaron
It's gonna be so funny that I'm talking and then all of a sudden, it's Josh's voice.
Josh Gondelman
They ADR'd in me.
Aaron
Well, how about. I'll do. These riddles are from. And then Josh, you say the name. Ready?
Josh Gondelman
Okay. These riddles are from Alex Dimitralis.
Aaron
Musical guest.
Josh Gondelman
Yeah. Give it a little Dumbardo Don Pardo. I said Dom Pardo, which is the champagne they drink after every episode of Saturday Night Live.
Casey
Well, it's not official unless it's been inside.
Aaron
Dom, you're in a habit of having fun with Nate.
Josh Gondelman
Otherwise, it's just sparkling. Darryl Hammond Pardo.
Casey
The interruption. Has anybody made that podcast? The All Don Pardo podcast?
Aaron
You guys are way more awake than me right now. This is quite intimidating.
JPC
Okay, you play flag football at recess and you say, like, I'm all time Don Pardo. That's who I'm playing.
Aaron
I love that I call these riddles couples. Each answer is a fairly common pairing of things, unless I'm unclever and really need to stretch the term common. With these three clues to figure out what the pair is. With three clues to figure out what the pair is. Sorry, what?
JPC
The pair is. Gotcha.
Aaron
Okay, and these are gonna be. These are pretty obvious. I will list them below and begin with one you may or may not use as an example. Okay, great. Thank you so much, Alex.
Casey
Alex who?
Aaron
Dimitri. Dim. Dip. Dimmit. I'm stuck. Pull me out. Pull me out. We are citrusy, covered in skin, and cannot be compared.
Casey
Apples and oranges.
JPC
No.
Aaron
Yes. You got it.
Casey
Oh, okay.
Aaron
That's a great. This is a good example, actually. I'd like to see a scene. We're going to see two roommates living together. It's kind of an odd couple situation. You're Trying to make it work. Josh will have you be an apple, and JBC will have you be an orange.
JPC
Got it.
Josh Gondelman
Right. Hey, can you help me with this box real quick?
JPC
Yeah, sure. What are we doing with it?
Josh Gondelman
Just. We're going to put it down, take some stuff out of it, and put it around the room.
JPC
Oh, um, I can't. I'd love to help you out, but just some of the stuff that you described is just gonna be so hard without hands and legs and eyes and a mouth and ears. And I love that for you, but it's just like, I might just lay her on the floor if it's all the same.
Josh Gondelman
Okay, that's fine. When you said ears, I don't even think ears were especially relevant to the task. It sounds like you're just trying to get out of doing it.
JPC
No, I know, but it's like you also have them, you know, and I don't. So it's like, kind of always relevant, you know? Kind of always relevant. Mm.
Josh Gondelman
So you're saying if you were a potato, you would be better equipped to help me out with this task?
JPC
All I'm saying is, is if the same witch that did whatever she did to you were to do it to me, maybe I would be more able to help with tasks around the house.
Josh Gondelman
It is. It is a little uncomfortable that the witch made me completely anthropomorphic and just gave you the ability to communicate psychically with.
JPC
Psychically with. Yeah. Yes. Yeah. And I don't think that. Did I do something to her? Like, it didn't feel like I did something to her, right?
Josh Gondelman
No, no, no, no. You are so nice to that witch.
Casey
We cut back to JPC and Josh in the witch's hut. Aaron youn are the witch.
Aaron
Do you mind taking your shoes off before you come in?
JPC
I'm sorry, are you talking to me, or you're looking at this bowl of fruit?
Aaron
Oh, sorry. Ooh, that's offensive. That's on me. Sorry. Do you guys mind taking your shoes off before you come in?
JPC
Are you gonna do something to the fruit? I mean, I feel like we went back in time to before the fruit got the ability.
Aaron
I thought that you were.
JPC
I'm sorry, I'm a neutral passerby.
Aaron
This is a complete misunderstanding, sir. Oh, you're thinking that you were born in orange and you got anthropomorphized. I'm thinking that you were a human who wronged me in some way. Okay. Sir, I thought you were a human that wronged me and I was gonna turn you into some fruit. I thought you were gonna not take off your shoes in my apartment. You. You, sir, you're gonna be an apple with legs and arms. You're okay.
Josh Gondelman
Okay. Still, that's weird considering.
Aaron
I'm gonna start screaming when there's misunderstandings and scenes. From now on, I'm turning over a new leaf and this is my new attitude on the show.
JPC
I do like the idea of, like two cursed people, but they never bring up the fact that they were people. They're just like. They're so used to being cursed pieces of fru that they're like, why even talk about it? Why even talk? We can't change anything.
Josh Gondelman
Stop bringing up the past.
Casey
I've always lived in the psychic orange.
Aaron
We fly.
Josh Gondelman
I also like that that's the specific misunderstanding with the witch that made you the witch.
JPC
She invited us here, Right? Like, I'm like, what? You? It's like, we don't want to be here for dinner.
Aaron
You didn't take off your shoes. Turn you into a fucking orange. Fuck you.
Casey
Big Twilight Z type cookbook that says how to cook for oranges.
Aaron
Oh, yeah. A classic.
JPC
A classic.
Aaron
We fly, feed our kids vomit and teach you how to fuck birds and bees. Yes. Adol, you're killing it. I'd actually like to see another scene. Adol, you are sort of a fun performer that has been brought into a middle school to teach kids about the birds and bees. And Josh and jbc, you'll be the students sort of asking him questions and poking holes in what he's doing.
Casey
And Aaron, maybe I'm drunk. Did you say middle school?
Aaron
Yeah, but high school, I guess. When do they bring in a sex ed person? We'll do high school. We'll do high school.
JPC
What is middle school? Well, it's like 6th, 7th, and 8th grade, right? I feel like that's right for sex.
Casey
We call that grade school. Okay, middle school.
Josh Gondelman
Really?
JPC
Okay, wait, you call middle school? Hold on now.
Casey
Elementary.
JPC
Okay, well, when I hear elementary, I think like one through five, right?
Casey
Okay.
JPC
Okay.
Josh Gondelman
Yeah. Maybe kindergarten tacked on.
Aaron
Yeah.
JPC
Can we be at kindergarten? No, no, you're right. Let's do seventh grade.
Aaron
You guys are like in eighth grade.
Josh Gondelman
It's funny that they had called that grade school because I've heard grade school as well. But all the school, they all have grades.
Casey
Yeah, that's fair. Wait a minute.
Aaron
This is the kind of stand up I want to see you be doing. Josh. This is the kind of observational comedy.
Casey
We're in a grade and we get grades. What's The. Okay.
Aaron
Okay. In action.
Casey
Hey, everybody. How's everyone doing? Give me a big old yay. Yay.
Aaron
Yay.
Casey
Okay, I heard some yays and some woos. We'll work on that. My name is Aspen and I'm here to teach you. Okay. Usually I get some giggles. No giggles from Aspen. Okay.
Adeline
Yes.
Josh Gondelman
Over there.
Casey
Aspen. Yeah.
Josh Gondelman
Why do kids sometimes giggle when you say Aspen?
Casey
Well, usually before I get to the pen part, they'll giggle at ass. Or sometimes people will whisper ass, penis to one another and sort of chuckle, but it's.
Aaron
We're really dropping the ball, guys. It sounds like other schools are funnier than us.
Casey
No, no, no, this is a good thing because you don't really know what asses and penises do.
JPC
No, no, no. We can do it. We can do ass, penis. Say your name again. Say your name again.
Casey
Don't go home and say that.
Josh Gondelman
It's not even time to go home for, like six hours.
JPC
Our teacher just told us to be respectful. But if that's not the vibe that you appreciate, we can do differently. We can do differently.
Aaron
We'll be like those other kids at the other schools.
JPC
Yeah. Say your name again. Say your name again.
Casey
My name. And I'm. And I want to make this clear. I'm definitely not Mr. Thompson in a hat and funny shoes. I'm Aspen the sex clown.
JPC
More like.
Aaron
Come on. You got it, stupid.
JPC
I just can't. It's just not who I am. I just don't like being this guy.
Casey
What the. Fuck me?
Aaron
No, no, the ass stick.
JPC
He told you that as. He told you that as a secret. You can't tell people his deepest, darkest fear, that he's dumb and unlovable.
Aaron
You didn't tell me that as a secret. I overheard him saying it backstage. It's different if I was.
Casey
And we need to get rid of our school backstage. If I was unlovable, then why does my wife have. Get the chalk out sex with me. Underline sex several times. What is. And what is sex?
Josh Gondelman
Hey, it makes me uncomfortable that the board just says sex with me on it.
Aaron
Yeah, yeah.
Casey
Let me get rid of that. Let me get rid of that.
Josh Gondelman
Okay, let's just write sex sounds like it's the assignment. You know what I'm talking about?
Casey
Yeah. Let me write sex. And then I'm going to write a bubble and it says learning about with an arrow circling back just so there's no.
Aaron
This seems a little complicated.
Casey
So no janitors call anyone. Okay, well, what do we know about. What do we know about sex? Parents have it. That sex is why you're here. Mr. Thompson has it. Your teacher, Mr. Thompson has a ton of sex.
Josh Gondelman
Why did you ask the question and then start giving all the answers?
Casey
Well, I just. I have my own little agenda. I want to work in Mr. Thompson. Absolutely. You know, cracks backs. Mr. Thompson is getting laid constantly.
Aaron
But I'm want us to tell people this.
Casey
You do what kids do if information gets disseminated. The semen. Let's talk about what do we know.
Josh Gondelman
I think he wants us to make fun of the word disseminated because it says semen in the middle.
Aaron
Anyone want to do that? Or.
Josh Gondelman
I don't want to take the bait. It feels too obvious.
JPC
Should we be making fun of just the word? Like what?
Josh Gondelman
I know.
Casey
What do we know? What are some. What are some? Genitals. We know. Let's just scream out. Genitals.
Aaron
Genitals.
JPC
Genitals.
Casey
Yeah. I walked into that one. Other teachers walking by the classroom. What the fuck?
JPC
Let's just scream that.
Aaron
Let's do one more. And then we'll come back to these after the break. We're fuzzy. Fall from the sky and assist those in physical or emotional need.
JPC
Acorn therapists.
Aaron
No, but write that down. That's something.
Casey
You mean squirrels.
Josh Gondelman
Jpc.
JPC
No. I don't go to a squirrel for therapy. No.
Casey
This guy's nuts.
Aaron
Jpc. It wouldn't. Nothing. And I'm saying this in a neutral way with no judgment, but I would be 0% surprised if I found out your therapist of the last decade was a squirrel. Everything would sort of lock into place for me. That you've been talking to a squirrel that sort of sits outside your window.
Adeline
This is.
JPC
I would also not find that because they have been acting so squirrely with me recently, to the point where I'm like something. It. Maybe it's not squirrel, but something is going on here. Someone call for a scene?
Aaron
No. We're fuzzy. Fall from the sky and assist those in a physical and emotional need.
Casey
Raining cats and dogs.
Aaron
Yes. Adel, you're on a roll here. Unbelievable.
Casey
I would like to see. Do we have time for it? A scene before break. Aaron or no?
Aaron
Yes. Let me ask the council. The council says yes.
Casey
Let's say Josh and Aaron, you two are dogs and you're trying to walk home in the rain. And jpc, you come in as a cat.
JPC
Okay.
Aaron
I think that you did really great today. Like, every time he threw the ball, you went. You grabbed it. You got it. I think that your confidence is just a little low. I don't know.
Josh Gondelman
I mean, I got it, but I brought it back and he threw it again, which probably means I didn't bring it back, right?
Aaron
No, no, I think he. If he. If he didn't bring it back, right, I don't think he would trust you enough to throw it again. You know what I mean?
Josh Gondelman
This is really helpful to hear because I was thinking that if you liked the way I brought it back, then he would have just kept it.
Aaron
Yes, he.
JPC
Pussy, please.
Aaron
What? Sorry. Hello?
JPC
Excuse me. Hello?
Aaron
Oh, it's a cat.
JPC
Did you say something to me? I'm sorry, did you say something to me?
Aaron
Stand behind me. Hey, can we help you with something? Oh, smells your butt.
JPC
Okay. Oh, okay. A little. A little personal, don't you think?
Aaron
I mean, it's how I say hello.
JPC
Okay. It's not how.
Aaron
Just making sure you're safe.
JPC
It's not how I say hello.
Josh Gondelman
So kind of feels like, oh, you do it.
Casey
You do it your way.
Josh Gondelman
You were just saying. Can you help you?
JPC
What's this guy. What's this guy's problem?
Aaron
He doesn't have.
JPC
Why is his face all flat like that?
Aaron
He's a pug.
Josh Gondelman
I'm a pug. This is how my face is that.
JPC
You say that like it means something to me. He's a pug. He's a pug. What could that possibly be?
Josh Gondelman
Also, I ran really fast into a wall, but that didn't make my face flat. My face was already flat, fortunately.
Aaron
Hey, man, you're the one who talked to us.
JPC
Yeah, I'm sorry. Wait, what do you. What? Why would you say that?
Aaron
Because you said. I think you called us pussies.
JPC
Excuse me? That's our word, which is a sort
Aaron
of takes one to no one situation.
JPC
I don't believe. I don't believe what I'm hearing right now. I don't believe what I'm hearing right now.
Aaron
No, I've met a cat before. You guys are dastardly and manipulative. You're all the same.
JPC
Oh, you know what you. You know what you are? A bigot.
Aaron
No, I'm a basset hound. Get it right.
JPC
Well, you. You know what? You look more like a bigot hound to me. And I said it. And I said it. I won't take it back.
Casey
Oh, my God.
Aaron
I can't believe I'm getting into a fight and I'm with my only pug friend.
Josh Gondelman
See, this is what I'm always saying about cancel culture running among. I'm sorry. Cancel culture running among.
JPC
You're that kind of culture. You're that kind of pug I see. What do you mean?
Aaron
Dark run upon catsel culture.
JPC
Catzel culture.
Aaron
Wow. And I think we should take a break. And I want everyone to really think about that. Okay.
JPC
This episode is sponsored by BetterHelp. All right, guys, it's JPC. And I want to tell you about BetterHelp's 2026 State of Stigma report, how we're really doing and why stigma still gets in the way of getting support. We all know that everybody has mental health to some degree. I certainly do. I've got actually a lot of it. And we're all talking about mental health more openly now. But asking for help can still be hard, and BetterHelp's latest research confirms it. BetterHelp's State of Sigma report surveyed 2,000Americans and revealed that 85% of Americans believe getting support is wise, yet 74% say society discourages people from doing so. I want to encourage you to get help and I love BetterHelp for that. With over 30,000 therapists, BetterHelp is the world's largest online therapy platform, having served over 6 million people globally. And it works with an average rating of 4.9 out of 5 stars for a live session based on over 1.7 million client reviews. Plus, BetterHelp therapists work according to a strict code of conduct and are fully licensed in the United States. And they have a therapist match commitment, which means they do the initial matching work for you so that you can focus on your therapy goals. And if you aren't happy with your match, you can switch to a different therapist at any time from their list of tailored wrecks. We simply have to eliminate the stigma that goes along with talking about mental health and doing something about it. Don't let stigma stand in the way of support. Start therapy with BetterHelp. Sign up and get 10% off@betterhelp.com Riddle that's BetterHelp. H-E-L-P.com Riddle hey everybody.
Casey
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 Camchata. 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 goop 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 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 Tempo meals.com riddle that's Tempo meals.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 no, that's a blackbird. Mmm, maybe Aaron. Oh it is Aaron. You're free. She just flew out the window. Classic Aaron.
JPC
Hey everybody, JPC here. You know, one thing I love about summer is how easy everything feels. The days are a little more relaxed and I find myself reaching for the same comfortable go anywhere pieces again and again. That is why I Love Quince. Quince's 100% European linen pants and shirts are breathable, easy to throw on, and the summer upgrade your rotation needs starting at just $34. I absolutely love their linen shirts. I wear my Quince linen shirts all summer long. They're light, they're breezy. It's the best feeling in the summertime. Plus their tees are soft enough to live in all day and the lightweight cotton sweaters are exactly what you want when the summer nights cool down. Everything at quince is priced 50 to 80% less than similar brands and they work directly with ethical factories and cut out the middlemen. So you're paying for exceptional quality, not brand markup. And it's not just clothing. Quinte has home goods, they have sheets. They became a trusted favorite from everything from home to travel to everyday essentials. Plus, I played Peter Quince in Midsummer Night's Dream when I was in high school and maybe one time after that. I think I've been in it twice. So make your summer wardrobe easier. Go to Quince.com Riddle for free shipping on your order and 365 day returns. Now available in Canada too. That's Q-U-I-N-C-E.com Riddle for free shipping and 365 day returns. Quince.com Riddle actually, guys, I've said Quince so much I'm now remembering I played Bottom the Weaver. I did not play Peter Quince and Midsummer Night's Dream in high school. And one other time after that, played Bottom the Weaver twice.
Aaron
Hey everybody, we're back from a break. That's Josh over there, that's Adol, that's jpc. And we're really excited to be here with riddles from Alex, Dimitri Demetri,
JPC
Dr. Demetrilos.
Aaron
Here are more of those couple riddles which I'm loving. These are fun. I feel like they're not.
Josh Gondelman
Oh yeah.
Aaron
It's early in the morning. I guess it's not early in the morning for me. It's 9:45am but this is the first thing I've done today. And so I'm glad that we're doing something that's kind of easy breezy on the brain. Here we go. We're Russian, litigious and are unjust when separated.
Casey
Crime and Punishment adult.
Josh Gondelman
You're so good at these.
Casey
And these are all words that are married to each other. I guess I just love my married friends.
Aaron
Yeah. Crime and Punishment are married, but they're in sort of like an open thing.
Casey
Yes. With War and Peace.
Aaron
Yes, exactly.
Josh Gondelman
They swing. The lifestyle.
Aaron
They swing.
Casey
Yeah. Warren. Peace of billionaire.
Aaron
We're clumsy, thirsty and crowned.
Josh Gondelman
Wait, what's that? Sorry.
Aaron
We're clumsy, thirsty and crowned.
JPC
Snap, crackle and pop. The three dwarves.
Aaron
No. Are you ok?
JPC
What question is that, Aaron?
Casey
Isn't there a show? I've never seen it, but I've heard of it. It's a show on Apple TV where it's like Lee Pace is both king. He's like himself, current age king, but then his younger self is there and his older self is there.
JPC
The foundation shows.
Casey
Okay. Asimov. I feel like now I'm just picturing Snap, Crackle, Pop in that sort of situation where they're all king at once. But past future versions.
Josh Gondelman
Those are the Three Kings from We Three Kings, the Christmas Carol.
Casey
Snapcrack Frankincense, gold and Rice Krispies.
Aaron
We are clumsy, thirsty and crowned.
JPC
Clumsy, thirsty and crowned.
Casey
Okay, this is. Now I'm thinking teeth like crown. Is that anywhere close?
Aaron
No, but is a crown like what
JPC
a king wears or is that. That's not gonna help me. No.
Aaron
Well, I guess, Yeah, I think it's. They're talking more about head. I actually don't know if they mean a literal crown. I don't think they mean a literal,
Casey
oh, Jack and Jill type.
Aaron
Yes. Jack and Jill.
Casey
Oh, it is Jack and Jill. Okay.
JPC
Oh, Jack and Jill fell down the hill.
Aaron
Went up the hill to fetch a pail of wine.
Josh Gondelman
But then they fell down.
Aaron
Jack and Jill.
JPC
I'm sorry, I was skipping to the end of the story. Spoilers. Jp fucking I. Jill fucking died, man. I'm so sorry. Hey, man. She was in a coma for 11 years. But no, you tell your story, Mr. Jack.
Casey
We're gonna pull the plug. Is that okay?
Aaron
Jack fell down too and broke his crown. And Jill came tumbling after. Do you think they mean like falling or do you think she did like a gymnastics tumble down the hill to come back?
Josh Gondelman
That would be so disrespectful.
Casey
After Jack broke, I think it was like a princess bride like my sweet Wesley.
Josh Gondelman
Yes.
JPC
Jack's bleeding out down there. She's just doing like a double backflip down there.
Casey
Watch me do a round off medics, hold up, scores.
Aaron
How are Jack and Jill related?
Casey
Dating, I thought.
Aaron
No, they're a pair of siblings. How about that?
Adeline
What?
Casey
Ew. I do want to see a scene.
JPC
Yep.
Casey
Aaron and Josh, you are Jack and Jill. And Aaron, you are visiting Jack in the hospital after the whole situation.
Aaron
Hey, buddy. How you holding up?
JPC
Jill, is.
Josh Gondelman
Is that you?
Aaron
Yeah. I brought flowers and balloons and I'm just here to apologize.
Josh Gondelman
For what? The whole thing was so hazy to me.
Aaron
Right?
Josh Gondelman
I just don't. I just remember we were going up the hill to fetch a pail of water.
Aaron
Sure.
Josh Gondelman
Which they kept at the top of the hill.
Aaron
Uh huh.
Josh Gondelman
And then yada, yada, yada, bottom of the hill, broken crown.
Aaron
And that's exactly what happened. And that's exactly what happened. You were very thirsty and you insisted we. We climb up there. And I said, that seems pretty unsafe. And then when we got up to the top, we weren't in a fight and I wasn't irritated and I didn't push you down the hill. So you remember it exactly. Right.
Josh Gondelman
Okay, quick follow up question. Jill, my best friend and closest sibling and only confidant.
Aaron
Of course.
Josh Gondelman
Why did you bring apology for flowers if. If that didn't happen.
Aaron
That's a great question, Jack. I gave them.
Josh Gondelman
I brought are saying I'm asking great questions.
Aaron
Oh, good.
Josh Gondelman
It was the first thing that came back.
Aaron
Good. I brought them for you to give to yourself. Cuz I thought you would want to exercise some self forgiveness after this entire incident.
Josh Gondelman
Now again, my memory. Memory is very hazy. Is that something anyone's ever done before?
Aaron
Yes, It's a very common normal thing that people do.
Josh Gondelman
Okay, then this sounds good. I just want to get back to normal. And the doctor said I might never do that again. Get back to normal.
Aaron
Well, the detectives are going to be in here soon and just make sure you tell them how hazy it is how you did this to yourself. If they throw around words like attempted or murder or anything like that, I just need you to just take a
Josh Gondelman
deep breath and I forgive myself for attempting to murder me. Understood.
Casey
Knock, knock, knock. Hello, I'm Detective Farts McNamara. Don't laugh. Usually it gets a giggle. And this is my partner.
Josh Gondelman
I'm sorry, I just have this grievous head injury. What part of farts McNamara or detective could be Detective? What part of Detective Fart McNamara do people usually giggle at?
Casey
Oh, great question.
Josh Gondelman
Thank you. The doctors are saying I'm asking great questions.
Casey
It's the first thing that came back, usually McNamara. Because people think of Mack the Knife and then they go into. Is that Sinatra?
Aaron
I think it's from Three Penny Opera.
Josh Gondelman
Darren.
JPC
That's right.
Casey
Bobby Darren. Thank you so much. I think I blocked it out because of who played him in the movie. Speaking of, this is my part partner, Detective Spacey. Kevin. He's a bit loopy.
JPC
Nice for me. Oh, and I know what you're gonna say. I got a fucked up face.
Aaron
Well, you're a pug.
JPC
Oh, I thought it was because I looked like Kevin Spacey.
Aaron
Scene. Let's keep going. Cared for by farmers, we spend the day in fields. Squeeze some fuzzy flesh and you get juice. Now don't be weird. Cared for by farmers, we spend the day in fields. Squeeze some fuzzy flesh and you get juice.
Casey
I mean, my first thought is peaches and cream.
Josh Gondelman
You got it too.
Casey
Okay, okay. But I was like, I can't picture a. When I picture farmers, I think of like tractors and corn. But peaches would be on a tree. But I don't think a farmer said at a tree.
Josh Gondelman
I also don't picture cream in a field.
Casey
You've never driven by a field of cream. Field of creams.
Josh Gondelman
I loved that.
JPC
If you stumbled upon cream. They Will Come. They Will Come. They Will Come Actually just works
Casey
well.
Josh Gondelman
Shit.
Casey
We accidentally made the best porn title of all time. Field of Prince.
Josh Gondelman
He tries to conjure the ghosts of baseball players to jack them off.
Casey
Honey, you're spending so much time outside. What's going on? Baseball, baseball, baseball. Think about it.
Aaron
I love baseball.
Josh Gondelman
He's the only guy that thinks about baseball and comes faster.
Casey
Well, and also, you know all the women that Derek Jeter dates.
Aaron
I. Josh, you'll appreciate this.
Josh Gondelman
Please.
Aaron
I. You grew up a Red Sox fan, I assume. I loved the Red Sox growing up and fell off a little bit in my twenties just because I was trying to get on the Cubs train a to be in Chicago. I was trying to be festive.
JPC
Aaron, that's called the red line.
Aaron
Oh, yes, the red line that got off at Addison. Thank you, jpc, for keeping me honest.
JPC
Fun local Chicago.
Josh Gondelman
Yeah. If you say Cubs train, they're like, what are you, a tourist?
JPC
Aaron's like, wow, the Cubs trade is so crowded today.
Aaron
But we had a night off on the Comedy Bang Bang Tour, and we were in Boston, and Will Hines, great improviser, was reading what the Boston Globe had been saying about the Red Sox this year. And it was. They were just ripping them apart because the Red Sox were in last place. And I was like, oh, man, that's really bad. And he was like, I'm gonna go to the game tonight. Anyone who wants to go with me can go. And I was like, you know what? It could be funny. It might be funny to watch the Red Sox be bad. I love Fenway Park. I'll go and have a hot dog. And I went. And it was by far the most exciting Red Sox game I've ever seen in person. It was, like, electric. And they were playing the Yankees, and they did six innings of the Yankees not even getting a hit. And I went, shame on me to doubt Boston. I feel like I learned a valuable lesson. I cannot believe I doubted the Red Sox. And now they're on, like, kind of a winning streak.
Josh Gondelman
Yeah, they've been playing really well. It kind of started with them sweeping the Yankees, and while they were still in last place and the Yankees, it took the Yankees from first place to second place. And as someone who's lived in New York for a long time, it still brought me great joy to see.
Aaron
Yes. And I was at that first game, their first Yankees game, and I went, wow, this is like good old Boston taught me a lesson.
JPC
Oh, so, Aaron, you did this?
Josh Gondelman
I would credit Aaron as Well, I
Casey
think Will Hines, you're a lucky talisman.
JPC
Well, I mean, yes, Will Hines did it in the way that he invited you to the game, but the actual, I mean, have you seen another, have you watched another of their games since then?
Aaron
No, but I did buy tickets for when they're playing in la.
JPC
Oh, Aaron, no. Oh, it's going to break their streak
Aaron
or they're still winning.
Josh Gondelman
Yeah, they could.
JPC
I know, but they could win harder, I guess. Yeah, I guess we, we. We'll have to, we'll have to follow through on that, Aaron, when, when they come to LA and see if, if it happens that you going to another game alters it in some way. Because all that we know right now, the empirical data has said that you have changed the trajectory for the better.
Aaron
I'm going to send you guys a text of a funny thing I saw at the game.
Josh Gondelman
I'm excited.
Aaron
Whenever I think of Fenway Park, I feel like the accent explodes out from there. Yeah, you're just bound to see the most Boston Y things ever. And there was a Yankees fan there and these guys in front of him every time.
JPC
Wow, that's you love. You love to see people being that aggro to a stranger.
Aaron
I love it.
JPC
Just the middle fingers in the face of a guy who appears to just be sitting there. Now, Aaron, was he antagonizing them in any way or was he in fact just sitting there?
Aaron
He was antagonizing them a little bit.
JPC
Okay, okay.
Aaron
He came in hot, being like, this is about to be just a humiliation ritual for the Red Sox. And then he left like an inning early and we all went, boo.
Casey
Now, to be fair, it is a Allen Houston, former Knicks player, Knicks jersey.
Aaron
Oh, it's a Knicks jersey.
Casey
And the Knicks won the championship most recently.
Aaron
So we all forget about that. That's ancient history.
Casey
I do feel like he's in the right New Yorker.
Aaron
Losers go Boston.
Josh Gondelman
It is funny though. Like, that kind of hubris isn't transferable when the Yankees lose. You can't then double back and be like, but the Knicks still won. Like, you kind of called your shot and you whiffed.
JPC
I do like the idea of wearing a basketball, like a winning basketball team to a different sports game because you're like, I want to get in a fight today, but I don't have the requisite jersey to get in a fight in the right way. But I still want to get in the fight. The fight needs to happen. Like, that's non negotiable.
Josh Gondelman
I let my kid take my Alex Rodriguez jersey back to his mom's house
Casey
and wearing a player's name. One of the only players whose last name is the city a different city?
Josh Gondelman
Yeah, third city entirely. I real quick if this is okay. I was walking down the street the day of Game 5 of the NBA Finals, and, like, all of New York City to this point had just been in a great mood for, like, a week, and since. Since they turned it around after Trump made them lose that one game. But, yeah, I was feeling great. I was, like, walking to meet my friend for lunch, and I saw an old lady with two little dogs, and I was crossing the street towards her and the dogs and just went, good morning. And she goes, who the fuck are you?
Aaron
And you're like, new York. So back.
Casey
All right, good morning. Good morning. That's your fucking step.
Josh Gondelman
It made me laugh so much, and when I told my wife about it, when I got up, she was like, how are you? Like, how are you laughing about this? That would have ruined my day if an old lady just screamed that in my face.
Aaron
That's so funny.
Josh Gondelman
It was awesome.
Aaron
It's like you were living in a musical for a week. Like, everybody's so sunshiny, and then she brought you right back to earth.
Josh Gondelman
Oh, it was great. It was, like, such a perfect experience. Lesson learned.
Aaron
I was gonna ask what it was like to be in New York when they won, but I feel like you
Josh Gondelman
just told us that was it. That was my dominant feeling, too, because I was, like, everywhere around me, people were so happy. Like, I felt like that lady for the whole week. Sure. Everywhere, people were happy. And friends would be like, are you going out after the game? Like, out in the streets? And I'm like, no, this isn't. Like, I'm. I guess I'm happy for you, but, like, I just live here. You know what I mean? I was like, this is. I would feel like a betrayal. Like, my sister was telling. She was like, my friends are asking if Josh is, like, cheering for the Knicks because he's lived there for so long. And she's like, I know, right? That's like a betrayal. And I'm like, yeah, of course it's a betrayal.
Aaron
Yeah. I would never.
Josh Gondelman
Disease. It's a disease to think that way, but I do have that disease, Josh.
Casey
I looked it up, and I'm sorry to say you ran into San Antonio spurs owner Samantha Texas, and so the one person who's going to be miserable.
JPC
Josh, is there any way that this old woman just couldn't maybe, like, modulate her voice? And what she said was like, who the fuck are you? Cause she's like, I know. I've seen this guy on YouTube. I know. I've been to one of his shows before, but it's like, I want to say Don Jondelman. And then she's like, no, don't say, who the fuck are you? And then she's like. And then you just walk past me, and she's like, don Jondelman is one of the rudest comics working.
Josh Gondelman
Wait. So I watched and I turned around to, like. To be like, is that what. And then she turned. Like we were past each other. We both turned around to look at each other again, and she went, who the fuck are you?
JPC
Oh, that's almost the Meet Joe Black stuff.
Josh Gondelman
You know, I did get hit by a bus after.
Casey
And now do your Jamaican patois.
JPC
The thing that people don't talk about enough is that he's killing it. He's doing the Jamaican patois. He's doing it exactly right.
Josh Gondelman
Brad Pitt. I don't. I think that's where my knowledge of Meat Joe Black ends.
JPC
I don't want to commit. It goes around every once in a while on the Internet. But there is a scene in Meat Joe Black where. Because he's like a. He's like an angel in someone else's body where he does like.
Casey
He's death, right?
JPC
Yeah, he's maybe death. Is death an angel. Who knows? But, yes, he's death. But he does. Is it, like, Jamaican? I can't remember, but it's some accent that is culturally, in the modern parlance, you probably wouldn't want to put yourself on screen doing.
Josh Gondelman
Sure, that's so. And. But that wasn't Brad Pitt.
JPC
It was Brad Pitt.
Josh Gondelman
Oh, it was Brad Pitt doing a Jamaican patois.
JPC
Yes.
Aaron
Yeah.
Josh Gondelman
It's also like a con that. It's the context, too, where you're like. I could see a context in which someone could do that in a movie, and you'd be like, oh, that's like, all right, whatever. But, like, in this case of like, no, no, no. This is drama. It's actually worse.
JPC
This is actually important. Hey, guys, can we have quiet on set? Brad Pitt's about to do his big scene.
Josh Gondelman
He's like. And this pronounced bumba clot. You know, we'll do some rewrites.
Aaron
Let's just make another movie.
Casey
I think my favorite Transformer, Bumbleclot.
Aaron
Awesome. All right, here's another one. This one I had a hard time with when I was playing along with myself to it earlier. So we'll see if you can do it.
Josh Gondelman
Okay.
JPC
Casey, go ahead and clip that for me.
Aaron
No. Come on. And I knew and I was trying to go under the radar. I can't say anything on the show without getting clipped.
JPC
No, I know.
Josh Gondelman
Yeah.
JPC
It's not fair.
Aaron
Builders of rainbows. Oath of the post. When contrasted, we are inevitable.
Casey
What was the first line?
Aaron
Builders of rainbows.
Casey
Leprechaun. Is this like, the lucky terms? Marshmallows. Like hearts and moons and clovers.
Josh Gondelman
Sunshine and rain.
Aaron
Yes. Rain and shine.
Casey
Good one, Josh.
Josh Gondelman
Amazing.
Aaron
The motion of boats found in garages. Together we are rebels.
Josh Gondelman
Rock and roll.
Aaron
Rock and roll.
JPC
Rock and roll. Rock and roll.
Josh Gondelman
Ebb and Flow is my favorite Pearl Jam song.
Casey
Ebb and flow. The dark and the moon
Aaron
Comparable to gold. Both grains of sand. We tend to push it. I really like this one.
JPC
Salt and pepper.
Aaron
Yeah.
Josh Gondelman
Ooh, that's really good.
JPC
God. The first one that I got. And not only the first one that I got, but the first one that, like, I understood.
Casey
Like, now say it like Patrick Stewart.
JPC
Excelsior.
Josh Gondelman
Ladies and gentlemen. Salt and Stanley.
Casey
Thank you.
Josh Gondelman
So good. A classic.
Casey
A classic.
Aaron
Aged French and pungent.
Casey
Wine and cheese.
Aaron
Yes.
Casey
It could also be Gerard Depardieu.
Josh Gondelman
Gerardo Depardieu.
Casey
Yeah.
JPC
If we're feeling particularly mean, it could be Gerard Depardu.
Aaron
French. An insult to children. We both have been around the world.
Casey
French. An insult to children. Jules Burner. Jules Hot Air Zeppelin. We've both been around the world. Amelia. Charles Lynn Burger Cheese.
Josh Gondelman
That's kind of a.
Aaron
Around the world is a reference to a song.
Casey
Oh, Daft Punk.
Aaron
Yes. Daft and punk. Yeah.
Casey
Very good.
Aaron
Favored in the morning, though often secretly craved for the evening. For a price, we will let you stay the night.
Casey
Bed and breakfast.
Aaron
Yes.
JPC
Oh, okay. Bed and breakfast. I fuck with that.
Aaron
Fried British bits.
Casey
Fish and chips.
Josh Gondelman
Pork and beans.
JPC
Fish and chips, of course.
Casey
And we blazed past it. But just know that I was gonna set up a Daft Punk bed and breakfast. But of course, we don't have the sun board for.
Aaron
We don't have anything for that. The fun for breakfast.
Casey
Fruit, cereal, milk and juice. Can you repeat that?
JPC
Adult pressing button. I'm. See, I'm envisioning you talking to a French robot person. And he's just like, apples, granola, milk and juice.
Casey
Wait, can you do that a little bit faster?
Aaron
That's so funny. The wolf's weapon. We are but wind splattered impotently against brick.
Casey
Whoa. Wind and bite.
JPC
The wolf's weapon is claw. Bite.
Casey
He blows down that tooth.
JPC
Tooth.
Aaron
But what is he actually? What are the words, the real words
Casey
for Huff and puff?
Aaron
He huffs and puffs.
JPC
Huffs and puffs.
Aaron
I'd like to see a scene. Adol, we're going to have you be a wolf that is sort of getting up there in age and is not as good at huffing and puffing anymore. And Josh, we're going to have you play a little pig whose house Adol is trying to blow down.
Casey
Ding dong.
Josh Gondelman
Oh, hey man, what's up? Sorry to.
JPC
Give me a sec.
Casey
Sorry, sorry, sorry, sorry.
Josh Gondelman
Can I get you a glass of water? I can't have you dying on this property. It's gonna raise a lot of questions. I'm so sorry.
Casey
Do you have a chair? Do you have a chair?
Josh Gondelman
Do I have a chair?
JPC
Do you have a chair?
Josh Gondelman
Yes, I have a chair. Do you want to sit in it?
Casey
Huff it up? Huff and I'll blow your house down.
Josh Gondelman
Okay. You sit in the chair for a minute. Okay.
Casey
Oh boy.
Josh Gondelman
I can't have detective farts MacArthur coming around here again. Ask if I killed another wolf.
JPC
Oh, you got kind of a flat
Josh Gondelman
face for a wolf.
Casey
You kind of live on a big mountaintop.
Josh Gondelman
Yeah, for privacy.
Casey
Oh. Back. Oh, if I was a teen wolf, I'd. What do you call me?
Aaron
What?
Josh Gondelman
You play basketball with me.
Casey
Yeah. Go for a layup and then you'd see me dunking on your ass.
Josh Gondelman
What? Let's cut to the chase. What are you doing here, old man?
Casey
I came here, but I came here. I bought the land that your home is on. We're going to demolish it. You have 30 days to vacate the premise. Back in the day, of course, I would huff and puff and blow your shit away. But now I'm older and I have saved and I have a 401k. So now I just buy the property and then sort of undercut the owner and knock down the place and build condos. So. You have 30 days to vacate the premise. You have been served.
Josh Gondelman
How about I knock you down this old hill and break your crown? How about that, huh? I live here. You. This is someone's life that you're talking about. This is a pig's life.
Casey
Yeah, that. Do you have that water?
Josh Gondelman
Do I. Do I have water for the guy that bought my house and is going to knock it down with the construction crew?
Casey
Hey, I'm not a bad guy, okay? I'm not a bad guy. I'm. I'm a businessman. I'm smart, okay?
Josh Gondelman
Oh, the big business wolf. No, Idiot. I don't buy it.
Casey
Yeah. Bbw. When you get older. What's your name?
Josh Gondelman
Pickleton.
Casey
Pickleton. When you get to be 45, 50, you're gonna realize that business is actually good. That. That.
Josh Gondelman
Don't condescend to me. This is actually good. You're gonna get more conservative as you get older, Wolf.
Casey
You live in your little pig bubble, and everyone says, oink, oink, and you say, all the way home. And you all just. It's just an echo chamber. You're gonna realize one day you have nothing. Okay. And then you're gonna realize you should have invested. You should have been a little more conservative.
Aaron
Hey, guys. Sorry to bother you.
Josh Gondelman
Yeah. What's up?
Aaron
Did you just see a really annoying brother fall down the hill just now or.
Josh Gondelman
Oh, I don't know if you're supposed to say that.
Aaron
Oh, well, ladies from Boston, have a good one.
JPC
Sing it up.
Casey
Oh.
Aaron
Oh, man.
Casey
Well, do we know if canonically, if this is, like, a brother's Grimm crossover, Do we know canonically, if the wolf from the Three Little Pigs is the same wolf from Little Red Riding Hood?
Josh Gondelman
I picture it as the same wolf.
Casey
Yeah.
Aaron
Yeah.
Casey
Is it written by the same. No. Jack and Jill would be like a Mother Goose. Right.
Josh Gondelman
But I don't think. Was that a real person?
Casey
I'm just thinking, like, I didn't know if there was, like, carryover. If it's like the wolf pops up again. I didn't know if the Brothers Grimm had, like, you know. Yeah, it's like CSI or something.
Josh Gondelman
Sure. Who wrote Brothers Grimm Hill?
Casey
Dick Wolf.
Aaron
Who wrote the Three Little Pigs? English. Fairy tale.
Casey
English. Interesting.
Aaron
In 1846, it first appeared.
Josh Gondelman
They were still doing that in 1846. They were still making up, like. And the pigs lived in a house.
Aaron
Yeah.
Josh Gondelman
Entertainment sucked back then.
Aaron
Oh, it's the worst. Oh, and then Little Red Riding Hood is way earlier.
Josh Gondelman
Okay, okay, that makes sense.
Aaron
Charles Perrault. It is French.
Casey
Whoa.
Aaron
Oui, oui, oui.
Casey
Erin, can we see one more very quick scene?
Aaron
Okay. Yes. Only because you've been good today.
Casey
JPC is a French big bad wolf airing your French little. Little. La petite. Thank you. La petite rouge. Hood.
Aaron
Yes. I love it.
JPC
Bother me, ma', am, but are you lost in the woods?
Aaron
Do you have a light for smoke?
JPC
Oh, holy shit. You're a child. Even better.
Aaron
No, see, see, see, see?
JPC
And that's a joke about how the. The French are all pedophiles.
Josh Gondelman
Why does your blackboard just say sex with me?
Aaron
Well, this has been fun. What a note to End it on Josh. Do you have anything to plug or promote or anything you want to talk about?
Josh Gondelman
Oh, my gosh. I have a comedy special that's out now on YouTube. It's called Positive Reinforcement. I put it out with Blonde Medicine Records. I have a newsletter called that's Marvelous. It's free or you can pay me money for it Every Monday. That's Marvelousnewsletter.com and then I'm on the road a ton this fall. I'm going. It's like ramping up now, but I'm doing Cambridge, Massachusetts, and gosh, I'm blanking right away. Oh, Dallas and Houston and San Diego and Phoenix and Cleveland and Pittsburgh already. And some more to come. Raleigh are on New Year's. Yeah, I'm really excited. Sorry, that's too many plugs. That's fantastic. No, but thank you for having me.
Casey
Thank you for having me.
Josh Gondelman
This is always so much fun.
Casey
One of our favorites.
Aaron
Anything to plug or promote. Anything you want to talk about.
Casey
Check out hello from the Magic Tavern. We're going to start our new season soon. We recently had Josh Gonelman on at the end of our last season, I believe. No, you were on Offices and Bosses.
Josh Gondelman
I was on Offices and Bosses and I think I might have done the last season of Magic Tavern.
Casey
Yes, yes. So check out Magic Tavern and also our Patreon, where you can find Offices and Bosses with Josh Gonelman. Aaron, do you have anything to plug or promote?
Aaron
Check out Quality Time if you're in Los Angeles or going to be in Los Angeles. It's a monthly variety show that I do. We're about to do July and the theme is rats, and we have an environmentalist doing a presentation on that. And I'm really excited. But we have a lot of really fun themes in the fall, so come check us out if you haven't yet. Gbc a review to read or anything to plug.
JPC
I'll just say if you liked Josh Gondolman on this show. Josh Goneman is also going to be guesting on an upcoming episode of our other show, Gum, Shoes and Dragons. So you can check him out there next month, which. Or maybe like in a couple of weeks, I think we haven't recorded it yet. So if something goes terribly wrong, then you might not. You'll never see Josh Goneman on that show.
Casey
Like the big bad wolf of the podcast universe, popping up everywhere.
JPC
Just popping up everywhere. Hot dogs.
Aaron
Oh, no, baby, baby, baby, touch me like this.
Casey
Granola milk and juice and salad, salad, breakfast salad.
Josh Gondelman
Casey.
JPC
Tony did the editing and Marty Paris in the music logo created by Emily Cardamus and Emily Naporus.
Aaron
And I think we should take a break. And I want everyone to really think about that. Okay?
Josh Gondelman
I'm gonna reset my recording. I apologize.
JPC
Oh, okay. No worries.
Josh Gondelman
Yep, I'm back up.
JPC
Perfect.
Casey
Thank you very much. I love you guys. Love you. He said it back.
Josh Gondelman
I'm gonna tell the rest of the gals and they are gonna be so excited for me when you go to
Aaron
lunch with them in the middle of the day. What are their names? Miranda, Samantha. Samantha.
Josh Gondelman
Charlotte.
Aaron
Sorry. I do listen when you talk about your friends, Josh. I just want you to know I am listening.
Josh Gondelman
That's okay. You're also one of my friends. Do you think you're not one of my friends, Josh?
Casey
I do listen to you. You have sex in the city or you have sex and the city?
Aaron
I think it's all in the city.
JPC
Oh, my God.
Casey
I'm so sorry.
Josh Gondelman
I actually do Saxon the city. Saxon.
Casey
Right on Fifth Avenue.
JPC
Hey there. Counts and quotes. If you like that, you are going to love this week's Patreon. It's another edition of our new games workshop. You can listen to that plus our entire back catalog@patreon.com heyrettlertle by joining the clue crew for $5 a month or start your 7 day free trial or the review crew for $8 a month. Plus you get those ad free episodes. See you there.
Aaron
That was a hitgam podcast. Hi, I am Mandy Moore.
Josh Gondelman
Sterling K. Brown.
Casey
And I'm Chris Sullivan. And we host the podcast that was us now on Headgum.
Aaron
Each episode we're gonna go into a deep dive from our show. This is us.
Adeline
That's right.
Aaron
We're gonna go episode by episode. We're also gonna pepper in episodes with different guest stars and writers and casting directors.
Casey
Are we gonna cry?
JPC
Yes, a little bit.
Josh Gondelman
Are we gonna laugh a lot?
JPC
A whole lot.
Josh Gondelman
That's what I'm hoping, man.
Adeline
Listen to.
Josh Gondelman
That was us on your favorite podcast app. Or watch full video episodes on YouTube or Spotify. New episodes every Tuesday.
Date: July 22, 2026
Guests: Josh Gondelman
Hosts: Adal Rifai, Erin Keif, John Patrick Coan (JPC)
This lively episode welcomes comedian and writer Josh Gondelman back for a riddle-packed improv spectacle. The core trio and Josh dive into inventive wordplay, classic improv scenes, offbeat personal stories (from karaoke adventures to Boston sports fandom), and a slew of whimsical “couple” riddles submitted by a listener. True to form, the episode’s actual riddles are only a springboard for tangents about childhood memories, pop culture references, and comic banter about everything from raccoon obstacle courses to the darkness of old children’s tales.
Notable Quote (12:15, Josh Gondelman):
“My friend Jaya Saxena innovated this: closing the night with a full room performance of ‘It’s All Coming Back to Me Now’ by Celine Dion. It’s such a long song and it’s so dynamic...you end up just like grabbing your chest and going ‘baby, baby, baby’.”
Sample Pairing Riddle Round:
(22:05, Aaron): “That’s a great—this is a good example actually...I’d like to see a scene...Josh, you be an apple, and JPC, you be an orange.”
(53:11, Josh): “I was crossing the street towards her and just went, ‘Good morning,’ and she goes, ‘Who the fuck are you?’... It made me laugh so much...it was great. It was like, such a perfect experience. Lesson learned."
On karaoke habits: (09:39, Josh)
“I've really settled into a groove lately with songs that nobody wants to hear... I'll do Dr. Worm by They Might Be Giants...it is a song that if you are not in the right room, people are like, that's not a song.”
On sibling dynamics and fairy tales: (43:46, Josh as Jack)
“Why did you bring apology flowers if—if that didn't happen?”
On Boston/New York rivalry: (49:40, Josh Gondelman)
“It kind of started with them sweeping the Yankees, and while they were still in last place...it still brought me great joy to see.”
On NYC street encounter: (53:11, Josh Gondelman)
“Good morning.’ And she goes, ‘Who the fuck are you?’”
Josh Gondelman:
Hosts:
| Clues | Answer | Timestamp | |-------------------------------------------------------------------------------|-----------------------|-----------| | Citrus, covered in skin, cannot be compared | Apples and Oranges | 22:02 | | Fuzzy, fall from sky, help those in need | Raining Cats and Dogs | 31:48 | | Russian, litigious, unjust when separate | Crime and Punishment | 40:46 | | Clumsy, thirsty, crowned | Jack and Jill | 41:15 | | Builders of rainbows, oath of the post, inevitable when contrasted | Rain and Shine | 57:22 | | Motion of boats, found in garages, together we are rebels | Rock and Roll | 57:44 | | Comparable to gold, both grains of sand, tend to push it | Salt and Pepper | 58:03 | | Aged, French, pungent | Wine and Cheese | 58:31 | | French, insult to children, both have been around the world | Daft and Punk | 58:52 | | Favored in the morning, often craved in evening, pay to stay the night | Bed and Breakfast | 59:18 | | Fried, British, bits | Fish and Chips | 59:33 | | Wolf's weapon, winds splattered, impotently against brick | Huff and Puff | 60:08 |
Casual, playful, improv-heavy, riffing between sharp wordplay and loving mockery. The podcast feels like hanging out with witty comedians who can’t resist a tangent or a callback (and rarely resist making a silly voice).
If you want riddles, you’ll get them, but you’ll love the ride!