Late Show Vocab | Bootsie
23 min
•May 17, 202614 days agoSummary
Stephen Colbert and producer Becca discuss personal stories and vocabulary from the Late Show, including a mystery about a Colbert Report set piece found at a flea market and an investigation into whether sex parties actually exist, featuring an undercover visit to a New York establishment called Sanctum.
Insights
- Personal memorabilia from long-running shows can unexpectedly resurface in secondary markets, raising questions about how gifts and collectibles are valued and distributed after employment ends
- Humor and authenticity in late-night comedy comes from genuine relationships and unscripted moments between hosts and staff, not just polished on-air segments
- Investigative comedy segments work best when they involve real deception and genuine discovery rather than fully staged scenarios
Trends
Late-night shows increasingly blur the line between scripted content and documentary-style field investigationsNostalgia-driven content about behind-the-scenes show history resonates with audiencesAuthentic staff relationships and family involvement in comedy production creates compelling narrative arcs
Topics
Companies
United Healthcare
Mentioned in pre-roll ad for Case by Case podcast about CEO Brian Thompson's death
CBS
Implied parent company of The Late Show with Stephen Colbert
People
Stephen Colbert
Host of the Late Show Pod Show discussing show history and conducting investigations
Becca
Producer discussing show memorabilia and vocabulary segments with Colbert
Carol
Found Colbert Report set piece at Chelsea Flea Market and gifted it to Becca
Jake Plunkett
Producer who deceived his mother Bootsy to send her to a sex party for a segment
Bootsy Plunkett
Mother of Jake Plunkett sent undercover to investigate sex parties at Sanctum
Kara
Former writer assistant who explained slang terminology to Colbert
Paul Krugman
Nobel Prize-winning economist mentioned as cover story for Bootsy's sex party visit
Quotes
"You must betray me in the wrestling ring"
Stephen Colbert (as a sleeping teenager)•Early in episode
"Boots. And I said that is, I'm sorry. I know that's like an imperative or something like that."
Stephen Colbert•Mid-episode
"I'm not going to a sex party. I'm not going to a sex club. I still don't believe it."
Stephen Colbert•Late in episode
"This is real because I found out tonight firsthand this is real."
Bootsy Plunkett•End of episode
Full Transcript
From the trusted team behind 48 Hours, welcome to Case by Case, your weekly update on the biggest true crime stories unfolding right now. Nick Ryder remains in custody without bail. Luigi Mangione accused of stalking and gunning down United Healthcare CEO Brian Thompson. From high-profile trials and stunning evidence to major breaks in cold cases, we'll follow it all Case by Case. Follow and listen to 48 Hours, Case by Case, wherever you get your podcasts. Bekka, I think I'll start this one off. If you don't mind. I mean obviously you're the producer. Your call. Are you good with me, starting? For now, I wonder what we're going to do with the names. What do we do? What do you do with like a 10-story Colbert on the outside? I'll take the C. I'll take the C. C is that's the hot one. That's the big one. I'll take the B. I'll take the B. No, you can take it for Bekka. Yeah, for B for Bekka. Oh, that's really funny. I don't think it's going to be my choice, by the way. I think CPS is. I don't know what they're going to do with it. If Dave is any indication of what they did to Dave, because that was harrowing the day after day finish, they literally pulled up a giant dump trucks or what is it called? Dumpsters out front and just through this unbelievable, really truly a work of art set in the garbage. Yeah, insane. But you don't know this. I have a piece of the Cobraire Pour Set. You do? I do. You guys, when you guys chopped up the paintings and put them in little acetate blocks, when I started my internship here, when I first moved to New York, my very sweet Aunt Carol found it at a flea market. And then when I started my job, she gave it to me. Wait a second. She found a piece of the Cobraire Pour portrait that I had encased in Lucite as a gift to everybody as we left the Cobraire Pour. And she found, because there's literally, there's only a hundred of them or something, because there's only 90 of us. I think we cut it into like 10 by 10, something like that. She found it in a flea market at the Chelsea Flea. Chelsea Flea, it's one of the best markets in the world in the city. I love it so much here in New York. She did. And now it's mine and I have it and it's great. All right, we're going to talk about this at rehearsal today. And I want to find out like, there's a lot of people wanted those. Yeah. And a lot of people wanted those. It ended up in great hands. I know, I know, I know, I'm glad you got it. But let me ask you this, what is the image of? It's just a little shard of red. It's like not. Oh, it's one of the edges. Yeah, yeah, yeah. It's one of the edges. Yeah. Yeah. My God. It might have been, it might have been like commiescentral exec, you know, you never know who it could have been. It doesn't, doesn't matter who it is. Those were, those were like cutting up a piece of me and giving it to someone. Oh, I'm so sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. God, why would, why would you tell me something like that? I thought it was a sweet. This thing that you gave away at the end of a 10 year show, we found one in the garbage. It wasn't, no, the flea market is very nice. It's pretty overpriced. But that meant, that meant that somebody, I mean, it's not like it's an antique, it's a vintage. It wasn't mean there was being sold on consignment. They found it in a, they found it in a throwaway pile. That's what those things are. I'm now hearing how this sounds, but it's a valuable piece of history. How much did, is your aunt, you said? Yes. How much did she pay for it? I don't know. Find out. Okay. Call her right now. Call her. Call her right now. Okay. Okay. We have a minute. We have a minute. Call her right now. Okay, great. Put her on speaker. Let's see. Let's see if she picks up. Put her on speaker. The tension is killing me. I know. Okay. Hello there. Hi, Carol. It's Becca. I have a quick question for you. I'm here with Steven. I'm here with Steven Colbert. We're recording some podcasts together. Hi, Carol. Hi. Hello. I told him the story about how you got me that piece of the Colbert report set from the flea market. Do you remember that? Yes. Wait, wait, which piece? The piece we're exploring is so far? No, no, no, no. It's, it's a little piece of loose site. It's like a bookend that you gave me that has a piece of the Colbert report set that you gave me in 2018 when I first moved to New York. And as part of the portrait that used to be on the set, in case in loose site. Do you remember that? No. Oh. Do, do give me a better description. It's, it's probably about the size of a pack of playing cards. It stands upright. There's a little scrap of like claw painted cloth in it, which was part of a portrait that used to hang on the set. And it's just perfectly clear with a piece of like red cloth in the center of it. And Becca claims that you got that at a flea market here at Chelsea Flea. And, and is that true? If she says so, then it's true. Okay. I was just wondering what you paid for it. Is it, did you pay paid cash for something like that, I assume? Yes, absolutely. Okay. Well, if you wouldn't mind just giving it some thought, if they, maybe you should send a photo of it to her. So she should recognize it. Yeah, tell me a photo and I will tell you because I, I imagine if it's that kind of collectible, I, I am pretty sure which dealer I bought it from, one of my regulars who has cool stuff. Oh, very cool. Okay. So if you can, if you do that, and then I wouldn't mind finding out, like that, I'd like to chase this down because those were, those were very like precious things that I gave to people with a lot of feeling behind them. And to find out that one of them ended up in a flea market has, has really just shook me to my core. And so I wanted, this is now a detective mystery. Yes. And I want to find out like how much it costs, where'd you buy it? Then I want to talk to that person and say, do you remember having this, where, where we've gotten from? And then where he got it. And then I want to confront that person with how it ended up in the flea market. I actually do have the magnifying glass and I'll put on my Sherlock hat. Okay, great. Fantastic. Great. And do my best. Okay. Great. All right. Somebody's, somebody's in, in big trouble or deceased. Okay. Because that's the only, that's the only possible answer is that, you know, you know, we haven't been doing it for 20 years. And there are people who have worked with me who I love very much, we're in longer with this. Yes. That is the only obviating factor that could possibly, you know, account for this ending up in a flea market. And if that is the case, I accept that entirely. I will not apologize for being upset, but I will accept that. Well, it was a really, it was a really beautiful thoughtful gift that you gave me, Carol. And thank you so much. And I'll send you the picture when I get home tonight. Excellent. Thank you. We're going to follow up on this. This is not the end of the story. Okay, great. Carol, your, your, your niece, Becca, is a delight to work with. And I am not the only one who thinks so. Oh, yeah. I have, she, she's an amazing, unique woman. And I've had the pleasure of knowing her for longer than you have. So we can share stories sometime. So I mean, no doubt you have known her longer than I have, but I bet I've spent more time in a tiny room. Yes. With her than you have. That is very true. All right. Love you, Carol. We'll talk soon. Love you, Carol. Have a great day. Okay, bye. Nice to meet you. She says, okay. Nice to meet you. Okay, bye. Carol, Carol's the best. Wow. Carol's the best. We love Carol. We love Aunt Carol. She's great. All right. Great name for an aunt. I know, right? It just flows. It's an Aunt Carol. Aunt Carol. All right. Well, I just thought it was a beautiful thing you guys did at the end of the show. It was. It was a beautiful thing. Yeah. I thought it was a very beautiful thing. Okay. All right. Well, you want to play? I mean, whoever, somebody might hear this and might know that I'm coming for them. Yeah. Yeah. Yeah. Yeah. Yeah. Quick, quick flash round. Maybe it was stolen. Keep going. It could have been stolen. Exactly. Heist. The quick round of Lachovokab. Okay, hit it. See in the wrestling ring. That means down in the theater or wherever that thing we need to do later. Okay, cool. I'll see you in the wrestling ring. It's related to something I said to my mother in my sleep when I was young. Oh. I was in high school. My mom came, got it, came into the room in the morning to wake me up for school and I sat bolt upright. As she describes it, still clearly asleep. And I believe her because I don't remember this. I sat bolt upright in bed. I looked her and I said, you must betray me in the wrestling ring. And I lay back down. And so that over the years has become to me that whatever the thing you have to do later that's going to be hard or you're nervous about is the wrestling ring. So I would say I'll see you in the wrestling ring. Oh, wow. That's really great. I never knew that story. And you say that to us almost all the time. See in the wrestling ring. Yeah. In other words, like that, good. We're almost there. And I'll see the final product later. I'll perform it later or you'll show me the thing later or we'll do the thing. You and I right now, we're in the wrestling ring. Yeah. We're in our casual pants upstairs in the writers meeting, but soon we will be in the rewrite basement. In our singlets. Yeah, yeah, yeah. In our singlets with a mouthpiece in and those things that keep for your ears from being torn off. Yeah, exactly. Okay, next one. This is the last one we'll do for today. Bootsy. Boots. Well, that's another one. Boots. Tell the Boots story. Well, one of our writers assistants, Kara, who is no longer with us. I mean, she's so live, but she's no longer with us. She's lovely, lovely person and did a lot of singing on the show, actually. Lovely singing voice. And she's young. She's young. She's my kid's age. And like you, she's young like you. But she's also very, as we say, with it. She's down with all the lingo. So I'd say, well, what does this mean? Like Boots King or whatever like that? And I'm like, what's Boots? Because it's just a saying. And I said, use that in a sentence. And she held her hands out and went, Boots. And I said that is, I'm sorry. I know that's like an imperative or something like that. Boots with an exclamation mark. Technically, that might be, no. So that's how I always, when I'm an old man and one of the young people tries to describe something to me, I'll often think to myself, Boots, you have done nothing to clarify what this means to me. Yeah, exactly. So Bootsy. Bootsy is a nickname of one of our staff members, mothers. Oh, oh, yeah, yeah, yeah, yeah, yeah. So it's Jake. It's Jake's mom. It's Jake's mom. Yeah. I want to play the podcast bit where we sent her to a sex party. Oh, that's what this is going to be. So on what happened was on air, I complained that I did not believe that sex parties were a real thing because I think it was Madison Cawthorne was briefly a congressman from North Carolina, a young man. And he said that he had been offered like cocaine and sex parties, like sex, sexual get togethers. I forgot he used a very awkward term for it. And I think I called into question whether those ever actually happened because I've been in show business since, like professionally, since I was like 24. And I mean, the comedians aren't big on the sexy end of the scale in terms of like, what's associated with them is not sexiness or romance or something like that. But I mean, I've worked at a mildly high level for decades now and no one's ever offered. And we're supposed to be, we're supposed to be the decadent ones. No one's ever offered me a bump of coke. No one's ever offered me, Hey, we're going to get together and just some super, super like, you know, cool people. And we thought maybe you'd want to come by and just be cool with us. You know, like, I've never got, we really liked your vibe. We noticed you across the party. And we just thought maybe let's all get together and celebrate, you know, the Emmys in our own way this weekend. No one's ever said that. They're just throwing go-go squeezes at our heads, you know? Exactly. We get nothing. We eat applesauce and we do another show. Apple talk about applesauce another time. But applesauce is a big thing with us. And so I called into question whether sex parties were real. And I got invited to, they called it a sex party, but it's really like a sex club. And it's in New York. And you have to have a membership. And so she went, we sent her, I'm like, I'm not going to a sex party. I'm not going to a sex club. I still don't believe it. Because that was in a professional endeavor. A sex party is, hey, we just love to get together and have sex with each other. And it's all kind of like, you know, we get naked in puppy pile, whatever. That's what, that's, that's a sex party. As I understand them. Again, never having been invited to a sex party. So I call, I mean, I think it's a really good piece. I'm glad we're gonna listen to it. But I call into question whether this is quote unquote a sex party. It's like going to a bar and going, Oh, I went to a great party last night where, Oh, at O'Shaughnessy's down in the corner, buddy, you didn't go to a, you didn't go to a party. You went to a bar. There was a, there was a, there was a, you know, there might even been a cover charge. Yeah. If there was a band, like you paid the gate. That's not a, that's not a party. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. No, I see what you're saying. You know what I'm saying? I know what you're saying. But yeah. So this is Bootsy. We call her the late shows uninformed correspondent, because she doesn't know what we're sending her into when we send her on a mission. She's fantastic. She's wonderful. And she's, the fights she has with Jake are my favorite part of it. And they're, I want you to know they're 100% sincere. They're yelling at each other is with love and none of it's made up. Yeah. And it's, I just wanted to be that. I just wanted to be Bootsy and Jake yelling each other for the entire time. Yeah. Wonderful. Yes. All right. And then because it always used to end with like, with, you know, I love you. Yes. Yeah. Yeah. Yeah. Okay. Great. Well, this is, this is Bootsy. Boots. All right. Thanks, Stephen. Have a great week. You too. Bye. Have a great weekend. Bye guys. Bye, Carol. Folks, if you watch the show, and I hope you do, you know that I, Stephen Colbert, have a few core beliefs. And one of the things that I believe is that there is no such thing as sex parties. I was a young man, a young teenager. I heard stories and rumors in the adult sex world that there were sex parties and orgies and flesh pits. Then I grew up and found out there's none of that. I've said this before, I just don't buy that sex parties are actually a thing. I'm in show business, supposedly the height of decadence. And I've never once been asked to a sex party. Well, folks, since I took that brave stance, I have been invited to multiple sex parties. That's how it happens. One of them was hosted by a group of folks called Sanctum. Evidently, it's one of those parties where you bring your own vowels. They have the T. You bring your A. Now, obviously, I wasn't going to accept the offer. I'm a happily married man who just won't shut up about sex parties. But it got me thinking, could I be wrong here? Have these sex parties been real all along? It was all so hard to understand. Well, thankfully, we here at the Late Show have an expert in not understanding things. Her name is Bootsy Plunkett, and she's the mother of my field producer, Jake Plunkett. She is also the Late Show's official uninformed correspondent. In the past, Bootsy has used her unique information light perspective to help us understand difficult issues, even sitting down to talk about trade tariffs with Nobel Prize winning economist Paul Krugman. So what occurred to me? I should send Bootsy to investigate what's really going on at Sanctum. Of course, Jake knew his mom would never agree to go to a sex party, so he did the right thing. He lied to her. He is a terrible son, but a great producer. Jake told Bootsy she was meeting Paul Krugman on a ferris wheel to talk about the debt ceiling, and then instead he brought her to the sex party. Jim? So yeah, we're going to have you have a little bit of a dinner with Paul Krugman. The he's an economist. Wait, Jake, what is he again? Economist. Economist. World renowned. Renowned economist. And what are you talking about today? Ceiling debt. Debt ceiling. Debt ceiling. Do you want to tell everyone how much you've mentioned Paul Krugman to me in the last two years since you had that dinner with him? Yes, I said that at all the things I've done. I like to pull up the best. He's very cute and quirky. You have a little bit of a crush on Paul Krugman. Oh, come on. That's in your words. You talk about him constantly. I do not. Yes, you do. Every time I see you on your iPad and you're watching one of your pieces. I never watch a piece. Yes, you do. That is bull. No, you're making it sound like I'm a Norsacist. For my mom and I, it was the moment of truth as we headed into the sex party known as Sanctum. I'm going to hell for this. Hello and welcome. Hi. May I offer you some champagne? Okay, thank you. Oh my god, she doesn't have a shirt on. Just a quick note if you see anyone or anything you like, please ask Consensus Key for touching your play. So would you like to see please ask with hands? Yes, why? Would you like to join us down in the van here? I guess. Is Paul here? Jake. So what's the- What? Paul's not here. You're actually at a sex party. Just go with him. I owed my mom some answers. So it was time to come clean. So you're not going on a Ferris wheel. Okay. There's no Paul. Oh, that's sad. So the story is, is that like Stephen has been denying the existence of sex parties in his monologues. And so there have been some invites to sex parties and the thought was that maybe you would be a good correspondent to go out and see if they exist. Oh, they exist. Unless this is a trick. So how are you feeling? I'm shocked. I mean, I'm handling it okay, but I'm not dressing up or nothing. Why? You know, I don't know what we're gonna see up there, but- What should I ask these people? Ask them about the debt ceiling. They don't seem like to give a s*** about my s*** debt ceiling. Now that my mom had her real assignment, she set out to discover if Sanctum was a real sex party. Oh, hi. Oh, Jesus. Oh my God. So you have these sex parties all the time? Yes, we do. We have them very frequently. This isn't like a joke? No, all the time. Do yous actually have sex? Yes, yes, we do. Oh, what? Oh, would you like a mask? Oh, no. No. Should I wear a mask? If you'd like, we have a whole bunch you can choose from. Oh my God. Oh. Is it good? Is it fit well? Yeah, it's just nice. It's nice. Oh, dear God, I'm gonna heart death. Is Stephen coming tonight? Does anybody know? Not that I was notified, so. No, huh? You're gonna have to bring the invite this time. You're like, I got it in. Come on, we're going. We're going? Scroogems, right? Wait. Scroogems. Scroogems. Sanctum. Sanctum. Oh my God. I get everything wrong. I'm sorry. Did you hear about the debt ceiling? Yeah, the debt ceiling. They're voting on it to hire it. I guess you don't know stuff either. So, is the room where you go up at night? After everything gets hot and heavy? Yeah, all the rooms are welcome for a play whenever you'd like during your event or whatever you call it. Me and the vigilante. I'm just interested. Wow. Wow. Very interesting. I learned a lot. We can ask the tub girls or the shower guests some of them or... Do you enjoy this coming here, obviously, right? Definitely. Yeah. So, this is the... This is more of our dorm room. The dorm room? Yeah. Do you like to give her a little tickle? Oh, no, no, no. I love tickle. You want a tickle with the pickle? Is it now going to be the case that whenever you hear the name Paul Krugman, you think of this? Yes. Yes. I wish I could talk to Paul. You could have never shocked me more than you did tonight. Hi, this is Bootsy. I'm here with the late show with Stephen Colbert. And guess what, Stephen? This is real because I found out tonight firsthand this is real. This is real. This is real. Okay, so that was bad because you didn't name what's real and where you are. I'm at the Spotums. Thank you, Bootsy. Thank you, Jake.