The transcript from this week’s MiB: Jay Leno, Live Audrain Newport Concours & Motor Week, is below.
You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube, and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.
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Transcript:
This is Masters in Business with Barry Ritholtz on Bloomberg Radio.
Happy holidays, and We have an extra-special holiday podcast at the Newport Ordering Concourse, elegance. I sit down with Jay Leno talking about cars, comedy, watches, and pretty much everything else. Jay’s a fascinating guy who’s created an amazing career.
I thought this conversation was super interesting, and I think you will also, with no further adieu, my conversation with the former host of The Tonight Show, Jay Leno.
Barry Ritholtz: Jay, thank you so much for joining us.
Jay Leno: Thanks for having me. So let’s start out with a little bit talking about your background. Uh, born in New Rochelle, you grew up in, um, Andover, Massachusetts. Which interest came first? Cars or comedy?
Jay Leno: Well, when you grow up in a little rural town, you don’t think of comedy as a job, you know? And I was known to the neighbors as Kathy’s boy wants to be comedian. He’ll grow out of that. He’ll say, don’t worry, Kathy, you, that, that kind of, you know, that kind of mm-hmm. People just, it, it didn’t seem like a viable, you know, you go to Hollywood, you meet kids wanna be lighting directors or costumes or, ’cause they know people that did that. You know, but when you’re in Andover, it’s like, what?
Barry Ritholtz: What sparked your interest in comedy? How did you find the path.
Jay Leno: I had very good teachers when I was in high school. I had a English teacher, Mrs. Hawks, and being dyslexic, I was not the best student. And you know, she said, “Oh, I see making jokes in class and stuff. Do you ever think of writing comedy?” I said, well, I never, I never thought it’d be a job. Oh, you should take, oh yeah, that’s it. She said, “I’ll tell you what. Why don’t you, maybe you could, instead of writing a paper for the final, you give a talk, you know?”
And I said, okay. And I tried to. Put some kid style jokes in and that was the first time in my life I actually enjoyed doing homework and mm-hmm. Well, maybe I can make a living doing this. But as a kid, you know, I think people at a comedians, you tend to remember things that are funny, things that get a reaction, you know?, I was in the fourth grade and Mrs. Allen was my teacher. I always remember this. She was telling us about, Robin Hood. how cruel the Sheriff of Nottingham was, and he would boil Robin’s men in oil, and I’d put my hand up and I said, you, you know why he did that to Tuck? And she said, no. Why? Because he was a Friar. Okay. And then she does one of these. “that’s not funny. Just stop that.” I, oh, see. Oh, she’s kinda laughing, you know. But the real kicker was later in the day, I’m walking past the teacher’s lounge. No, no. Come here. Well, what did you say about Friar Tuck? I said, and I went, oh, she told my joke in the teacher’s lounge and I said, oh. I said, he is a Friar. Oh, that’s was a friar, that’s a very funny thing. I went, oh, that’s, that’s pretty good. And I thought, oh, and when you’re a kid, you, you know people that you tend to remember things that get a laugh.
You just sort of, a little bit of attention. Yeah. You put them in your mind, you try, it makes a little indentation, you know? So that was always something I enjoyed doing. Always remembered it. But again, I never thought. I could make a living doing it.
Barry Ritholtz: Who were your comedic influences when you were growing up?
Jay Leno: Oh, Robert Klein, George Carlin. Richard Pryor, primarily Klein. ’cause Klein was like me, middle class white kid. You know, most comedians at that time tend to be, uh, grew up during the depression. Mm-hmm. And Youngman, uh, all those kind of guys, you know, kids today with the long hair, you know, all that kind of stuff.
Then all along comes Robert Klein. And, and, uh, and, and once again, George Carlin. Richard Pryor, Bill Cosby before the recent turn of events. Uh, you know, so it, it was, yeah, those were my influences.
Barry Ritholtz: Since we’re at the ordering Concourse and Motor Week, let’s talk a little bit about cars. (Good transition, right?)
Your first, your first car was a 34 Ford stock. What’d you do to it?
Jay Leno: I saw my dad and I were driving past the tip top miniature golf in North Reding, Massachusetts. It was parked at the Shell Station with a sale sign. I went and I bought it. Um, what’d you pay for that? $350. Mm-hmm. Which was a lot of money in Yes, in 1965.
But I had been working at McDonald’s and I’d saved some money and, you know, so, and then we dragged it back to my house and I took a couple years to get it running, and then I got my license and I drove it every day to school.
Barry Ritholtz: Self-taught mechanic. What do you mean? You took a couple years to get it?
Jay Leno: Oh, self. Self. Well, yeah, I mean, just. You know, you’re a kid, you’re playing with it after school, you know, that kind of thing. Uh, yeah, it took me a couple of years to learn how to do. Yeah, I guess self-taught would be the fair way to say it. Yeah.
Barry Ritholtz: So 34 Ford is the gateway drug. At what point did you realize this is more than a hobby, something of a passion.
Jay Leno: Well, when I had a garage full of cars, I Perhaps this is, uh, more than a Yeah, yeah.
Barry Ritholtz: Well, how many cars is too many? At what point do you need help?
Jay Leno: Just maintain, well, I have 214 on the road now. Plus the motorcycles.
I watch the show hoarders, and go, the guy’s fine. It’s a problem, man. You can still get to the bathroom. Look, but that’s old newspapers. You have motorcycles and cars. Something a little more reasonable when your parent did the same thing.
Barry Ritholtz: How do you decide of the 214 cars, which one you gonna take that day?
Jay Leno: That’s the first world problem. Mm-hmm. That’s not very much. So people don’t want to hear a rich guy go, how do I decide? I just can’t decide which guy. No. I mean, whatever I’m working on. If I do one oil change a day, it takes 18 months. So, right. You have to look at it that way. Right.
Barry Ritholtz: Watever you’ve just worked on, you say, let me drive it home to see if it’s okay.
Jay Leno: So that’s what I enjoy.
Barry Ritholtz: You’re a little bicoastal, you’re in L A but you also have a place here in Newport?
Jay Leno: I do have a place, and I also have a house in Andover, Massachusetts, where I grew up here.
Barry Ritholtz: Do you, do you keep any cars out here as well?
Jay Leno: No, I don’t. Because of the weather and mm-hmm. You know,
Barry Ritholtz: What do you drive when you get here?
Jay Leno: I’m one of these people. Really my car, you know? If my car was on another coast, oh, that would be horrible. Like, we go out to eat if, if I can’t see the restaurant from my table, we’re not eating here, honey.
Barry Ritholtz: I’m curious how Leno’s Garage came about. I have this fantasy that your accountant says to you…
Jay Leno: No, no, no. I have a garage, I have friends with cameras, I’m on TV already. This seems like a fairly natural transition.
Barry Ritholtz: Why don’t you take the TV hobby and put it on tv and this way you try to mo, um, you know, monetize it as much as you can?
Jay Leno: I did it for nothing for the first, I guess, 15 years. Really? Yeah. You know, just because I enjoyed doing it. It was fun. Um, and it just opens up another, you know, you should have something. I’m not a particularly interesting person. Uh, you know, so if you have other things of interest that other people like, then you have something in common, you can talk about it. So, cars, motorcycles. Anything that rolls, explodes, makes noise is interesting.
Barry Ritholtz: Do you know what the cars, uh, that are top of the list here are gonna be?
Have you walked around, seen much so far? Oh yeah. This, you have some of the best cars in the world here. This is quite an event. You are. And inevitably you see something you’ve never seen before or, or never even heard of.
Jay Leno: You know, the, uh, all countries are working on automobiles. In different, you know, you had cars from Czechoslovakia, the people on the other side of the mountains never heard of. Mm-hmm. You know, like a Tatra, a very unusual car. Most Americas never seen one, but it’s very popular in Czechoslovakia or what was then Czechoslovakia at the time.
So, yeah, so it’s a fascinating hobby and the nice thing about it is it’s no more than really 150 years old. You know, if you, if you like Egyptology, well now you gotta go back 6,000 years and stand in hot sun and dig in the sand. And, uh, you know that with cars, I only have to go back a few years. We, we took a walk down, um, the Boulevard earlier, the two that kind leapt out to me, aside from the Gulling, I know you have one of those was the Talbot Lagos.
Yeah. Spectacular. Yeah. Very interesting guy. They’re very art deco, you know? Yes. It’s only in recent years, cars are seen as kinetic artwork. Right. You know, it used to be just an old car. Mm-hmm. But now people are looking at them and I mean, it’s. You know, you can buy a painting that this for a hundred million dollars.
Right? You get something that rolls down the road, looks pretty, has a practical element to it. So, and only cost a 10th as much. Yeah. Only cost a 10 or sometimes, almost as much you Right. I mean, Ferrari go for the, I think the last Ferrari sold for $75 million. Yeah. I mean it’s pretty crazy. That’s a one of one though, right?
No, no, that’s one of 13. 13, wow. Yeah, I also saw, um, uh, and there wasn’t a sign on it, so I’m doing this. By sight, but a Mercedes SK 500, the giant front fenders has Yeah, yeah. Spectacular. Also, they are, they, I try to enjoy the, the, the, some suspicious things happen in Germany, even. Thirties to the mm-hmm.
Middle forties. I tend to avoid those for obvious reasons. Mm-hmm. But the early ones I love. Yeah. So let, let, let’s talk about some of these classic designs. What do you think has aged especially well? What looks good? Uh, perhaps that wasn’t thought of so well, when it first came out. Oh. Oh, what his age?
Well, I wasn’t thought when it first came. Well, two different court, I mean. Uh, shapes evolve. I mean, uh, cars used to change just for the sake of change. Mm-hmm. Now they change mostly because of aerodynamics and efficiency and, and things of that nature. You know, uh, I mean, a Prius is about an efficient shape as you can get, but it’s not, it’s attractive enough, but it’s not striking.
It doesn’t take your breath away the way. Mm-hmm. Some Ferraris by pin or whatever, you know, back in the, in, in the twenties, thirties, forties, fifties. Things are drawn by hand. So there’s a, there’s a, a flow. Yeah. Flow. Yeah. Like now everything is sort of computer design. You have all these sort of weird angles and things like that, but.
Uh, you know, the best looking cars are both masculine and feminine, like an XKE. Mm-hmm. I don’t know any women that don’t find Jaguars attractive. Even women that don’t know anything about cars, there’s something about, because it has a feminine element to it, but then it has the rear haunches and, and so it has a masculine, so it’s a little bit of both to it.
Mm-hmm. You know. A lot of cars look too brutal. You know, Lamber, goodie, Kosh? Mm-hmm. Those look like guy cars, right? You drive, one of the girls go, how old are you? Yeah, boy toy. You pull ’em a jag, you’re like, Ooh, I like that guy. Yeah. So sometimes the proportions, the shapes, the lines, they speak to everybody.
They’re universal. Yeah. I mean, it’s trick is. Well, if it speaks to everybody, then you have a Corolla. Mm-hmm. You know, the, the best. Cause people, some people love it, some people hate it. Anything that gets emotion going is probably gonna work on some level. You know, I remember talking to Bob Lutz about this when the Viper came out and said, A lot of people think it looks like a cartoon car.
It’s a bit over exaggerated because we’re not trying to sell it to them. We’re trying to sell it to the people who think it looks good and there’s enough of ’em out there, you know? For sure. So, so let’s talk about, um. People have to ask you questions about cars all the time, but they don’t have to.
Actually. Most of ’em just, people must assume. Lots of people do. Yeah. Yeah. When someone asks you for a recommendation, what, what, what do you recommend as a good, cheap set of wheels for a budding enthusiast? Well, you know, there are almost, or for an enthusiast mm-hmm. Or for transportation. Transportation is easy.
I mean, someone who wants something fun for the weekend, well, first they tell me what it is they’re looking for. You know, I, I, I mean obviously el cars, Mustangs, Camaros, things of this nature. Any sort of two seated sports car, uh, yeah, there’s plenty of choices out there. You don’t need me for that. Mm-hmm.
So this event is sponsored in part by Alanga and Sauna. Mm-hmm. Um, we’re both wearing Longa watches. What drew you to watches? See, I paid for mine. So did I. Oh, you did? I paid for mine also. So, so, and you probably have access to more of these than I can get, so, well, it’s interesting, you know, I, I, watchmaking and automotive things have a lot in common ’cause they’re both extremely mechanical.
Mm-hmm. Most watch people don’t really like electric watches the same way they don’t like quartz watches. Mm-hmm. Quart watches are obviously the most accurate you can get, but there’s, don’t appear to have a soul to ’em, you know, with these kind of things, when you turn, you hear the, the, you know. Mm-hmm. It is, it’s a sort of a.
The car, the watch needs you. If you don’t wind it, it won’t run. So there’s a human element that needs to be attached to watch, to get it to the run, you know? And if you flip it over, you can see the absolute spectacular mechanicals on the other side. Yeah. They do a beautiful job. So, so very parallel the, the precision and intricacy of a mechanical watch and a classic automobile.
Yeah. Yeah. I, I, I seen them as somewhat similar. I mean, I like things that need me, you know, my, my cars need me because I need to do certain things to make sure they run correctly. Electric cars kind of run them out of who the master is. Mm-hmm. You know, it’s about like that screen door. After a while, you learn it has to be shut a certain way.
Normal people can’t do it, but you know that you lift it and turn it just a quarter of an inch, oh, it’ll click in. Coming up, we continue our conversation with Jay Leno, live from the Newport, a Drain concourse, the elegance, discussing how a career in comedy. And car collecting led to a fascination with mechanical time pieces.
I am Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Jay Leno, comedian, car collector, timepiece enthusiast. Let’s return to our conversation live at the Newport or drain concourse Gonz. What, what are your thoughts on, on the new EVs and hybrids that are coming out?
What, what does this do to the collectible market? I, I believe you have a Tesla plaid, is that right? A Tesla plaid’s a great look. I used my electric card during the week. I mean, sitting on the freeway in a 40, a 1966 Hemi, 4 26, it gets three miles per gallon. Doesn’t really make a lot of sense. You’re not going fast, you’re not, you’re just annoying people and, and poisoning the atmosphere.
So you take your electric car then on the weekends. If there’s a car rally, you drive your Mustang or whatever car you have to the rally, you sit around and you tell lies about it to other people and they tell you lies about their car and you know, it’s a sort of, a little bit of interaction, you know, so, so I mentioned the precision of automobiles and the precision of watches.
You have famously been touring for 40 years, 40 plus years. Um, when you put together a standup set, do you put the same sort of precision into structuring that set as you do? Well, I think, I like to think so. Mm-hmm. I mean, you, you, you, you want to have a joke every six to nine seconds. It’s a bit like spinning plates of the Sullivan show, and then, then you want to keep it going, you know?
So you wanna make sure that the people, you’re not wasting people’s time. I hate when people are, how y’all doing? Woo. Anybody from Boston? Woo. Boston? Yeah. Okay. That’s not comedy. You’ve wasted 40 seconds. You know, get right. Yeah. Keep it moving. You know, when you watch Rodney, Rodney was a, I was a big fan of Rodney Dangerfield, and it was, it was the economy of words.
It’s getting the funniest words you can in the shortest amount of time. You know, Rodney had jokes I loved, like, uh, I worked practice strip joint. It said topless and bottomless. I went in. There was nobody there. I mean, it’s, it’s a funny joke. I mean, ’cause I didn’t waste your time. It wasn’t a three minute setup.
You know, one of his favorite jokes, it’s so stupid. My doctor wanted a semen sample, a stool sample. And a urine sample. So I gave my underpants. I mean, okay. But it’s quick. Boom, boom, boom. You’re not, you’re not wasting people’s time. Really. Interesting. So you’ve been known as somebody who just has toured his whole career, even during, what was it, 22 years of the Tonight Show?
You still were doing standup on a regular basis? Well, when you’re on television, you rely on 175 other people. Mm-hmm. They really can’t do the show without all the elements to it. And when you go out on the road, you’re by yourself. You rise the fall strictly on your own ability. And I, I, I like that you get all the blame, but you also get all the glory.
And, and I, I like that. Plus it’s piecemeal, right? Joke, tell joke, get checked, boom. Next show nobody says, you know the joke she told two months ago, they’re not working out. Come back. You gotta come back and do the show again. You don’t have to do that. You know? Mm-hmm. On tv you get, there’s so many irons in the fire and whatnot.
You’re dealing with. You know, and my, my favorite TV line of all time when NBC was letting me go, I said, you know, I’ve been number one for 23 years, well for 18, 18 of the 23 years. And they said, we want what’s above number one? I said, okay, what, uh, what is above? What is above number? I mean, just made me laugh.
And even they realize how stupid that song. I said, what do you mean? How can you have, what’s a above? Just tell me, somebody tell me what it, yeah. Just made me laugh. Sorry. So since this is Bloomberg, a financial network. Yeah, let’s, let’s talk a little bit about money. Alright. You are known as someone who is savvy with your money.
You only spent the money you earned doing standup. Well, I’m not savvy. I’m dyslexic. Yeah. Okay. So consequently I don’t really understand it. All I know is money. My I work and my money relaxes. That’s my, I don’t want my money out working for me. Because he’s gonna screw up somewhere. I don’t want that.
Right. Whenever I hear, and there’s minimal risk, and I hear the word risk. Mm-hmm. And minimal. So that means I’m gonna lose something, right? No, no. I, no, I don’t. I always had, even as a kid, I worked at Wilmington Ford, I worked in McDonald’s. Whichever job made the most I banked and the other money was my, you did the same with The Tonight Show.
You banked The Tonight Show. I never touched a check in 22 years from The Tonight Show. That’s amazing. I banked everything and I lived on the money I made as a comedian. Then when I, when I, uh, when the show ended it, oh, I opened this little pass book. Oh look, this. It’s quite a bit of money here, you know?
This is good. Yeah. So when you started collecting cars, did you ever envision this collection would get this large No. No. Or this valuable? No. I never thought that, no. When I, I remember I would sleep in the alleys in New York and it was the most depressing. I remember sleeping on the alley. It was one of those alleys where guys would come with hookers and I’d be in the back just hiding behind some trash cans and they were doing whatever.
Really, this is my life now. I mean, it was like. It’s the most horrible that really on the road you were that hard travel. I remember on 44th and ninth it was Dikes. Lumberyard, right across the way and from from the alley where I slept a couple of nights I could see dikes lumberyard. I always had that in my mind, and hookers would come in and they’d just, just horrible.
It’s a terrible, they just hear terrible sounds horrible. I said, really? This is my life. This is what it is now. You know? So everything better than that was gravy. Yeah. Well, it’s been a little bit of gravy. You recently had a, uh, gulling, you found in a barn you’ve had a number of barn. No, no. I, no, I didn’t.
I didn’t buy that. I didn’t buy, that car was found. It was sold for $10 million and we had the owner You had it on the show? We had it on the show, yes. I did not. I, I would like to have owned that car, but no, I didn’t buy it. Didn’t you find a number of barn fines, cars? Oh yeah. Sure, sure. What, what are some of the more memorable ones?
Um. Well, the most recent one was a 1963 Jaguar XKE. Uh, the guy bought it in 62, started drinking about 66, 67. He became a hoarder, just had trash piled on top of it. Uh, when he died, the family called me, they said, uh, cars right across the street. Uh, my uncles had some kind of car. We didn’t know what it was.
And it was a Jaguar. And I, I said, and, and this is really the best way. I said, look, Google it. Find out what’s it worth. Okay. Find out what they’re worth and let me know and I’ll pay you that. And that’s what I did. Seems fair. Yeah. I, I mean, I paid more than a fair price. Mm-hmm. Because I, I don’t flip cars.
I don’t sell cars. So to me, this way, nobody goes, you wanna rip me? I don’t, you don’t want any of that? Any cars on your list that you’re still, uh. Hunting for anything you’d like to have? No, you know, I buy, I buy the story as much as I buy the car. Really? Yeah. I mean, to me the fun, you know, I had a lady call me 94 years old, and she and her Hudson, her and her husband bought a 51 Hudson Hornet in New Jersey.
They drove it to California with their two kids. He bought a gas station. He ran that for the next 30 years. He died sometime in the early nineties. She calls me about 2000, I guess. Three, four. Uh oh. My husband died like 20 years ago. We got this car. I say I already have a 5,300 will come look at it. Okay, so I gotta look at it.
She’s 94, no hearing air, no glasses, right? And she said, would you gimme $5,000 for her? Okay. So I bought it. I take it back to my garage. It takes about a year and a half. We get it off and let me see if she’s still alive. I call her up. Hello? Oh, it’s jaylenn off. I said, the car’s all finished. You want to go for a ride?
She goes, okay, now she’s 96. Okay. And she says, can I bring the kids? I said, yeah, bring the kids. So I get there and the kids have got a blindfold and the kids are 74 and 72 and they’re blindfolded or right. And she’s like touching the car. Oh, the paint feels so smooth. Oh, it used to be so rough. We’ll take the blind.
Oh, she starts crying. We wanna go for, let’s go for araj. So the kids get in the back. Right. So we’re driving along and we’re talking, and the two kids start doing this to each other, poking each other, right? And, and she turns around. I, I told you kids, and she’s whacking the crap out of me. Mr. Leno was nice enough to take us a ride in his car, and you kids can’t be here.
And the three of them are just laughing. I mean, they’re just falling down. And she, and she’s not holding back. I mean, she’s really hitting them, but she’s laughing while she’s hitting them, you know? And it was just so funny. It was just so funny. She lived to be 106. Wow. And every time I get in that car, it makes me laugh.
’cause it was just so fun to see these, these two old men and they all look the same age. You know, she’s 96, they’re 74, and, and she just whacking the crap out of hilarious. So more stories than there’s a hole in your collection or you’re enamored with this? No, don’t have a hole. I know. I have enamored with this.
No, it’s just about the stories. You know, my key to success is low self-esteem. I’ve heard you say that before. Yes. Yes. Because. If you have low cycle esteem, you never assume you’re the smartest person in the room. I assume one of the dumbest person in the room. So let me look around and see what the other people are doing here, and that’s what you do.
You know, I have so many friends that do TV shows and they really think, I don’t like, I wanna change these lights. And the lighting director who’s been in the business 40 years, I don’t think, no wait, I wanna change. Well, no. Why? Why don’t just let the lighting director do his job? You know, the fun thing about the Tonight Show was when I did it, anybody could pull, pull a cord and stop the train because I don’t like this.
I don’t think this is funny. Did it get to be annoying sometimes? But everybody felt they had a, a say in what was going on. It felt like they were part of the whole system. This idea that, you know, do not make eye contact with the star and just all that kind of nonsense, you know? So to me that was always the key to, to, to being successful.
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I am Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Jay Leno, comedian, car collector, timepiece enthusiast. Let’s return to our conversation live at the Newport or drain concourse Gonz. So, so let’s stay with, um, the Tonight Show and comedy.
All right. Um, you’ve interviewed a few presidents, right? Right. Um, you interviewed Barack Obama. Who, what other presidents did you interview? Uh, was Barack Obama. Was Reagan before you, uh, started on, no, I, I interviewed Reagan. They had dinner with Reagan at the White House a couple times, but he wasn’t ever on the show.
Barack Obama was the first sitting president ever to do the show. Mm-hmm. Um. Uh, Barack Obama, Hillary had the nomination locked up and then he announced he was running for president. So I called him up and said, wanna come on the show? Oh, we’ll call. Thank you so much. You know, he rented a car, drove himself to the show, you know, walks out.
I goes, Hey, my name’s Barack was saying Obama. I’m running the president of the United. I said, okay, black guy from Chicago named Hussein. I said, you know, you shouldn’t even have to campaign. I just think you, you’re shooing with that. And you know, he got the joke and he’d laugh and he was very funny. And we got to be friends.
And so next time he came on the show, I asked him, it was the first time a sitting president and the whole parking lot was tented. Mm-hmm. So a satellite could not see where, when it came in, where it came in, couldn’t tell. Yeah. And I mean, I’ve told this story, but this is. I have the same idiot friends I had in eighth grade, so I’m telling him I had Barack Obama on the show and he gave me this phone number.
Nah, Uhuh Uhhuh. Uhuh Uhhuh. You don’t get it. You said you now, alright, let’s call him up. I go, I’m, it’s surprising the United States, I’m not gonna call him up. No, you don’t have it now. Uhuh Uhhuh now Uhuh Uhhuh. So I, I take out my phone book and I cover the phone and they go, see what it says there. Barack Obama president, the United States, his phone number is right under here.
You you? I said alright. Alright. I’ll call him. You want me to call him? Ill call. It’s like three o’clock, I figure. Okay, what can go wrong? Yeah. Hello, Brock Here. Mr. President. Yeah. Jay Leno. We’re gonna do vj. I’m just here with some of my friends. Lose this number. Jay, click. So your reputation has never been, uh, a very political.
Uh, comedian, you play it straight down the middle. Well, I used to get, we used to get quoted every day in the New York Times. We, we, we tried to make fun of both sides. Yeah. Mm-hmm. But yeah, that’s the way we did it. That’s not the way everybody else does it, but that’s okay. So, so recently Jimmy Kimmel mentioned on the air that you called to check in on him when, when he was temporarily suspended.
Uh, is what do you think the future of late night looks like? And and what does that say about the comedians have to watch what they say. Well, apparently they don’t have to watch what they say ’cause he’s back on tv. Mm-hmm. Okay. I mean, you either believe in free speech or you don’t, you know, free speech.
It only becomes annoying when it says something you don’t like. Mm-hmm. Other than that, it’s fine. And that that’s really the only, the only problem. And there’s always something somebody doesn’t like, whether it’s banning books or Huck Finn or whatever it might be. Uh, so to me, I, I always support street. I mean, I support Jimmy as a comedian, but also just the whole premise.
You don’t have to agree with him to realize. I mean, I, I, I had people that tore me apart every day. But they had the right to do it. I, I, I didn’t like what they said, but I agree with their right to say it if they chose. Yeah. You, you have Dave Chappelle speaking at the comedy festival in Saudi Arabia.
Mm-hmm. Saying he feels like, uh, free speech is under assault in the us. Uh, not that Saudi Arabia is a hotbed of free speech. Well, yeah, yeah. Again, I, I don’t like this new thing of comics criticizing other comics. We’re comedians. Okay. Just, you know, I believe in free speech. I, I shouldn’t have to say any more than that and I will defend it.
To the end, but, you know, and how about when he said this again, whatever, I don’t have to agree with it. Mm-hmm. You know, it’s like the Nazis marching in Skokie. Okay. They, they have the right to do that. I don’t agree with it. Well, I He like to see someone punch them in the face. Yes. But I don’t want that to be police doing it.
If some angry Jewish guy was about, well, okay, it’s fine with me, you know, I might even cheer him on, but I’m, no, I, I, I, again, I think you hit. It’s America. You have the right. And what about the, in the era of streaming, what about the future of late night? We heard Colbert is supposedly not profitable. I don’t know how true that is.
We heard similar threats about Jimmy’s show. How do you look at, you were a steward of the Tonight Show for 22 years. What do you think the future of this looks like? Well, I, I, I mean, when you could turn on streaming. And see Harrison Ford talk for half an hour saying whatever you want unscripted. Or you could watch him do a seven minute segment on a talk show, which you gonna do?
Or Jay Leno for 45 minutes unscripted. Yeah. But yeah. Well, I mean, to me, I think it just, the nature of television, it, it changes. It goes from one thing to another. I mean, it’s like going from CD players to cas cassettes, to CDs to it is just another. It’s another format that, that you can, that you can use.
So, uh, the thing that really kills late night is the incessant number of commercials. Mm-hmm. After 1130, you can run like nine minutes at 12 o’clock where some crazy. Yeah. It’s crazy. It’s wild. Yeah. So, and when you realize you’ve just watched all three Godfather movies in a row without one commercial, suddenly seeing Jake from State Farm again.
You know, okay, enough with this guy, you know, to me that’s the thing that’s really hurt. Late night. It’s not necessarily what people say. It’s the fact that people, oh God, another commercial, you just, you know, reading through. All right. So we don’t want to keep you all day ’cause we know you have a lot of places to go, cars to see.
Alright, I wanna, I wanna do a speed round, uh, a speed round, right. A dozen questions in under a minute. I’m just gonna throw these at you and, and gimme your answers. Alright. Starting with, what’s your favorite car to drive a dusenberg, what’s your favorite motorcycle in your garage? Uh, brush superior. What car offers the best bang for the buck?
Corvette, what’s your favorite car in your collection? Not necessarily a driver, but just the favorite car. Uh, McLarin one. That’s, that’s tough one to argue with. What’s been the biggest maintenance annoyance in your collection? Uh, my 1925 Doble Steam car. The one that kind of blew up. Is that the one we’re talking about?
That blew up, but that wasn’t the one that actually blew up in my face. No. Any cars you have any regrets passing on? Oh yeah. Was all. What modern car features do you find most annoying? Uh, probably the infotainment system. Uh, you know, I have my 51 Hudson. I reach out, I press a button, I get a station. I don’t have to stop and look at it.
Are you happy this thing? Yes. Would you make this election again? Yes. Others have made this election. Would you continue? Yes, I would. You know, would you pick your language? English is good. Thank you. You know, I it annoying. Um, what car do you drive the most often from your collection? Oh, I don’t know. Uh, well, hmm.
I drive a lot of them. Cardo. Uh, that’s what they were made for. A model t’s kind of fun, I guess I don’t drive it that much. Uh, probably the Mustang. That’s pretty good. Well, actually the Tesla won’t have to go to the airport and all those kind of things. What, what’s the rarest car in your collection? Not necessarily the most valuable, but one of very few.
Well, that would be the double steam car. Yeah. Mm-hmm. Um, is there any one brand you would never buy that you stay away from? No, no, not everyone breaks you. You don’t have a lot of Ferrari, right? No, I don’t have any Ferrari. But it has nothing to do with the cars. The cars are excellent. You know, for the longest time you had to buy two Manial before you’re allowed to buy the car.
You, you know, so I just never took part in that. What car surprises people the most, whether driving it or just the way it’s put together? Well, I have the kind of cars people. Not surprised that I got there earlier, late. They’re surprised I got there at all. When you show up in a 1906 Stanley Steamer and it’s on fire, people like, oh my God, your car’s on fire.
Yeah, I know. It’s supposed to. It’s supposed to be. You carry open flame in. Um, what’s the most recent addition to the collection? A Mustang, GTD. What’s the best sounding engine you own? Uh uh, um, Porsche GT V 10. And final question. Oh, is, is there one dream car you’re still hunting for? No. No. I’m, I’m, I’m.
Quite happy with what I have. Like I said, be happy what you have. Just make sure you have enough. There you go. Thank you Jay, for being so generous time. Alright, well thank, thank you. Thank you.
That was my live interview with Jay Leno at the Newport Audrey Concourse Elegance. If you enjoyed that conversation, check out any of the 592 we’ve done over the past 12 years. You can find those at iTunes, Spotify, Bloomberg, YouTube, wherever you get your favorite podcasts. And be sure to check out my new book, how Not to Invest the ideas, numbers, and Behavior that Destroys Wealth and how to avoid them at your favorite bookstore or book seller.
I would be remiss if I did not thank the correct team that puts these conversations together each week. My videographer at the live event was Sebastian Escobar. Alexis Noriega is my video producer, Anna Luke is my podcast producer. Sean Russo is my researcher. Sage Bauman is the head of podcast here at Bloomberg.
I’m Barry Ritholtz. You’ve been listening to Masters in Business on Bloomberg Radio.
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Audrey Strauss, acting U.S. attorney for the Southern District of New York, points to a photo of Jeffrey Epstein and Ghislaine Maxwell, during a news conference in New York. / PHOTO: Associated Press
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The U.S. Food and Drug Administration in White Oak, Md., on June 5, 2023. Madalina Vasiliu/The Epoch Times
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