"What’s the Most Gangster Thing You’ve Ever Done?!" - Jimmy Carr Responds - Chicago, Illinois

18 Sep 2026 · 13 min · 6 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Jimmy Carr performs Crowdwork in Chicago, taking audience questions and riffing on “the most gangster thing I’ve ever done,” plus internet trolls, city comparisons (Chicago vs New York/Detroit), and edgy hypotheticals.

Key claims

he says his “gangster” act is tax avoidance—“how they got Capone” and “how they got me.” He jokes his phone “turns off” when hearing something, and uses blunt insults while discussing trolls.

Notable examples

he debates ketchup on hot dogs and Chicago pizza vs New York pizza (marriage vs brief affair), references Malort and Ma O’Brien’s, and recalls a Rodney Dangerfield story about the Comedy Store.

Guests

no named guests; audience members include a 15-year-old girl named Nova and her stepdad/family, plus other crowd participants.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Gangster Talk and Food Preferences

0:30 to 1:41

Jimmy engages the audience with humorous banter about preferences in pizza and ketchup.

“Hello, I'm Jimmy Carr and this is Crowdwork.”

Chicago vs. New York Pizza Debate

1:41 to 3:06

A funny comparison between Chicago and New York pizza styles, using metaphors.

“I'll tell you what's better, your fucking pizza.”

Audience Interaction and Bragging Rights

3:06 to 4:25

Jimmy interacts with the audience, showcasing his local connections and humor.

“Very happy to pull up to your bumper, baby.”

Detroit's Revival and Personal Anecdotes

4:25 to 5:43

Discussion about Detroit's resurgence and funny anecdotes about past experiences.

“I'm going to a place called Ma O 'Brien's.”

Gangster Movies and British Crime Culture

5:43 to 8:06

Jimmy discusses gangster films and his perspective on British gangster culture.

“There's a certain satisfaction when you work with someone.”

Controversial Questions and Audience Humor

8:06 to 10:12

A series of humorous and provocative questions posed to the audience.

“Yeah, that and a bit of Peaky Blinders, that's kind of, that's Gangster.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00And we're back. Streaming on Peacock. May I present to you the award-winning staff of the Toledo Truth Teller. Slap me. Let's jar something loose. Ay, yes! I like that. The certified fresh series returns. Your boss. You always like this? Or is this just an act? Oh no, this is mad. Oysters, everybody! There is a certain satisfaction when you work with someone. Maybe we could be a family. You sadistic pig! The Paper. New season streaming September 9th, only on Peacock. This show gives me a reason to laugh. Hello, I'm Jimmy Carr and this is Crowdwork. This one is from Chicago, where I seem to remember having a pretty good gig.

0:36And appropriately enough, I talk about the most gangster thing I've ever done. How do you handle internet trolls? How do I handle internet trolls? Ah, I've got a thing. When you hear about this, you're going to feel like a fool. My phone turns off.

1:00It's almost like it didn't happen. Huh? You like ketchup on your hot dog! Do I? Do I what? Do I what? Do I what? Do I like ketchup on my hot dog? Oh, I'll fuck you on the rag, yeah. Yeah. Yeah.

1:21Yeah. Yeah. Yeah.

1:32You didn't mean that literally, did you? Like as a, yeah.

1:40Oh, no. There's mustard on this. Wow. No. Wow! You need to see someone. Your healthcare system's fucked. Huh? Chicago or New York, which is better? Which is better, Chicago or New York? I'll just hang on, I'll check. We're in Chicago, yeah? Chicago.

2:10I'll tell you what's better, your fucking pizza. Jesus wept.

2:17But, I would say, I would say like a New York pizza, delicious, delicious, but it's like having a brief affair with a lady. I'd say a Chicago pizza is like a marriage. That's going to be with you for a while.

2:34Driver or passenger. What's the word? Driver or passenger. Driver or passenger. I don't know what this relates to. Is this like the Roman... Because the Romans thought of sex very differently, didn't they? They didn't think of straight and gay. The Romans were sword and sheath. I'd be more of a sword than a sheath. So I'm going to go with driver.

3:06Very happy to pull up to your bumper, baby.

3:13Yeah, finally some Grace Jones references from the 80s. I would not normally say this, but fuck me what a beautiful theatre.

3:31I appreciate people buying a ticket to any show I do, but tonight I get to be in Frank Sinatra's dressing room. It's so fucking cool. The ghost is still there, yeah. Any teenage girls? There's one there. Hi, what's your name? Nova. What, sorry? Nova. Nova, hi Nova. How old are you Nova? Fifteen. Fifteen. Okay.

4:03You've done nothing wrong. Who's brought you here this evening? This guy? Is that your dad? Stepdad? Okay.

4:24Well, we've all seen it online but you never think you're gonna meet him.

4:34What's that mean? Have you tried Malort yet? What, sorry? Have you tried Malort yet? Have I tried what yet? Malort! Malort! Malort! Malort! Malort! It's a Chicago booze. I'll fucking try it later. Right. I'm going out to a bar later on. I'm going to a place called Ma O 'Brien's. Has anyone heard of this? Someone's heard of it. My cousin's got a pub in Chicago. Serves a very nice pint of Guinness. I'm going there. Am I buying drinks? Sir, I don't pay for drinks. Please.

5:19Do I know Anya O 'Brien? Yeah. She's my cousin. She's your friend! She's your friend? Yeah, but she's my fucking cousin.

5:33So fuck you, lady. Of course I know one of you, yeah. Least favourite city? Least favourite city? Well, why, I didn't come here to shit on Detroit. Why, why, why?

5:52actually that's fucking unfair i had a fucking great gig there and that new shinola that guy who's the guy that's put all the money back into it there's one guy that's and we're back streaming on peacock may i present to you the award-winning staff of the toledo truth teller slap me let's draw something loose ah yes i like that the certified fresh series returns Your boss, you always like this or is this just an act? Oh no, this is mad. Oysters, everybody! There's a certain satisfaction when you work with someone. Maybe we could be a family. You sadistic pig! The Paper. New season streaming September 9th, only on Peacock.

6:29This show gives me a reason to laugh. Put billions back into Detroit and it is popping at the moment. It's fucking great on a Saturday night. It's a bit unfair. That's a reference from 15 years ago. Double day with Rodney Jangerfield. So where would you go? A double date with Rodney Dangerfield. I ditched the women and go to the comedy store.

6:51Apparently Rodney Dangerfield, on his third marriage, he went to the comedy store on the way home from the ceremony and did a 10-minute set. And his wife was at the back of the room in a wedding dress.

7:08Wow. Wow. I, uh... What did you think of the rapture? What did you think of the rapture? The rapture? Yeah, they took away all the good people. I don't think anyone in Chicago was affected.

7:26What's your favorite drug? What's my favorite drug? To use on yourself. To use on myself. Thank you.

7:40That's very good.

7:45Jimmy, you're in Chicago. What's the most gangster thing you've ever done? Ahhhh. Tax avoidance. Tax avoidance is how they got Capone. It's also how they got me.

8:05there was that remember the time I smashed someone's head on the table with a baseball bat because he was disloyal

8:18it was one of those two I don't really know how gangster a British man can be huh huh Snatch, that's a fucking great movie, isn't it? Yeah, that and a bit of Peaky Blinders, that's kind of, that's Gangster. Yeah, The Gentleman, Mobland. I mean, we make an effort, The Craze, pretty good, but eh. Lock, stock, lock, stock. It's cool. I like Guy a lot, he's a good guy. Yeah. I remember, you know Snatch, I don't know if it was the same here, but Snatch came out the same week as Shaft.

9:01And we only had two screens in the town I grew up in, and it just said snatch and shaft. And I thought, well, they go together. That's a double bill. If you went back in time ten years, ran into your past self, and for some reason you started fucking yourself, would that be considered gay or masturbation?

9:35I have to ask, who's asking this question? Just maybe raise your hand if you are a closeted homosexual man.

9:51It's not just gay, it's fucking incest.

9:58Let's go live to our incest experts.

10:08I'm so sorry. LAUGHTER APPLAUSE Thank you very much for coming out. I very much appreciate it. We did it, we had fun, right? We had fun. Thank you very much for coming out, everybody. Thank you, I very much appreciate that. I'll see you next time. Take care. Good night. APPLAUSE The best day of my life was the birth of my first child. And that's because that was the day someone told me you don't pay capital gains tax on selling gold coins. That's why I partnered up with a pure gold company. I buy gold with them as a store of wealth and to protect against inflation. And, well, you can do that too.

10:56This is an advert. I'm suggesting you do that. But I'm not a financial advisor. Don't take my advice. Go and, you know, seek a professional financial advisor and then do what I tell you. Go and buy gold at the pure gold company. They'll tell you it's a good idea. I am not a grifter. I wouldn't sell you something that I don't use myself. So I use the Pure Gold Company. If you'd like to invest in physical gold as well, just click the link in the description or head to the pure-gold.co slash jimmy to get your free copy of their investor guide. That's pure-gold.co slash jimmy. Mention my name when you speak to them and you'll get six months of storage secure for your bullion absolutely free.

11:34My God, I'm good to you. I hope you enjoy the clip. I just want to say this. The best presents are never things, they're experiences. So if you're having difficulty in your relationship, if the passion is fading, then don't get her flowers or chocolates or jewellery. Buy her tickets, take her out, come and see me live. Give her the best gift you can give anyone. No, not the gift of laughter. A night with a real man. Click below for tickets, you cuck.

12:07I present to you the award-winning staff of the Toledo Truth Teller. Slap me. Let's jar something loose. Ay, yes! I like that. The certified fresh series returns. Your boss. You always like this? Or is this just an act? Oh, no. This is mad. Oysters, everybody! There's a certain satisfaction when you work with someone. Maybe we could be a family. You sadistic pig! The Paper. New season streaming September 9th, only on Peacock. This show gives me a reason to laugh.

From the publisher

While performing in Chicago, Jimmy Carr is asked, “What’s the most gangster thing you’ve ever done?” His answer? Not quite what the crowd might have expected!

To see Jimmy on tour go to http://jimmycarr.com for tickets.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
If you are looking to protect your wealth with physical gold, then I highly recommend The Pure Gold Company:
⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://pure-gold.co/jimmy⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Just click the link in the description to get your free copy of their investor guide.

Mention my name when you speak to them and you’ll get 6 months of secure storage for your bullion absolutely free.

Learn more about your ad choices. Visit megaphone.fm/adchoices

More from Jimmy Carr: Crowd Work

All 71 episodes
"What’s the Most Gangster Thing You’ve Ever Done?!" - Jimmy Carr Responds - Chicago, IllinoisJimmy Carr: Crowd Work · 13 min
Listen in VO