Chitra Ragavan

Jon Macks

Ep 23 — A political strategist loses his mojo and becomes one of the greatest comedy writers of our time / Jon Macks, Comedy Writer, Democratic Political Consultant, Author.

Jon Macks thought he was in for a great ride to the top. Having quit law school for a career as a political strategist, Macks won two big state elections for his clients.

But the euphoria quickly wore off and shock set in when Macks then lost 23 straight races in a row.

“It’s almost self-fulfilling. What happens is that when you are on a losing streak, no one good will hire you,” says Macks, “And so they don’t have much money, they can’t win the campaign, they don’t have the skills, and so then you rack up another loss. So basically at that point you’re in a position where you have to somehow convince one person to take a chance on you.”

And that’s exactly what happened. Macks began his upward trajectory as a political strategist again, traveling tens of thousands of miles for many winning candidates.

To keep himself occupied on those flights, Macks wrote free-lance jokes and sent them in to the rising star stand-up comic, Jay Leno, who was about to become Johnny Carson’s successor on The Tonight Show.

One thing led to another and Leno offered Macks a full-time writer position on the show.

It was the beginning of an amazing career in stand-up comedy.

During his 22 years on The Tonight Show, Macks wrote an estimated 500,000 jokes, getting a record 18,000 on the air.

He’s also written for top comedians including Billy Crystal, Martin Short, Steve Martin, Chris Rock, and famous actors. And Macks has maintained a parallel career as a top strategist and writer for democratic political candidates and even some U.S. Presidents.

In this fascinating interview, Macks talks about how he surmounted his early obstacles in politics and went on to become one of the most prolific and successful comedy writers in history.

The author of five books, including his most recent, Monologue: What Makes America Laugh Before Bed, Macks dissects the anatomy of winning jokes and ruminates on what makes some work so well while others fall totally flat.

Macks shares what it’s like to write for the current slew of democratic political candidates.

And last but not least, he reveals some of his tradecraft on how he is able to write more than 100 jokes a day.

The quintessential Jon Macks, on this episode of When It mattered.


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Chitra Ragavan:   Jon Macks became a comedy writer in a roundabout way. He had quit law to become a political strategist. He won two huge campaigns, but then his luck turned on a dime. Macks started writing jokes when he was on flights, one thing led to another, and he became one of Jay Leno’s most successful writers on The Tonight Show for 22 years. Hello, everyone. I’m Chitra Ragavan and this is When It Mattered. This episode is brought to you by Goodstory, an advisory firm helping technology startups find their narrative.

Chitra Ragavan:   Joining me now is Jon Macks. He’s considered one of the greatest comedy writers of all time by the likes of Billy Crystal, Steve Martin, Chris Rock, and Martin Short just to name a few. Macks has written for 22 Academy Awards. He’s written material for high-profile clients including Helen Mirren, Michael Douglas, Hugh Jackman, Arnold Schwarzenegger and others. The author of five books, Macks also is a sought-after democratic political consultant and a speechwriter for political candidates, and even some US presidents. Jon, welcome to the podcast.

Jon Macks:   It’s great to be here.

Chitra Ragavan:   When you told me earlier that you had won two races followed by losing 23 races, my first thought was, “Wow, people really trust this guy. They keep hiring him even when he’s consistently losing campaigns.” How did you convince people to keep hiring you?

Jon Macks:   Well, it was actually a little bit less of convincing people that I was really good and getting people who were really at the bottom of the barrel. It’s almost self-fulfilling that what happens is that when you are on a losing streak, no one good will hire you and so they don’t have much money, they can’t win the campaign, they don’t have the skills, and so then you rack up another loss.

Jon Macks:   So basically at that point you’re in a position where you have to somehow convince one person to take a chance at you and generally, and at least for me that worked out the same way it worked for James Carville. We ended up working for a guy named Bob Casey. Bob Casey had run for governor three times and lost. So basically no one really wanted to work for him when he ran for a fourth time. No one would hire James Carville who had never won a race, and no one was really interested in hiring a guy who lost 23 straight, so we were a perfect combination.

Chitra Ragavan:   So you then ended up getting back on the horse and you started winning races?

Jon Macks:   Yeah. What happened was that after Governor Casey won, after Bob Casey at the time became Governor Casey in ’86, what happened was I started to get interest from media consulting firms as opposed to just being a one-off of running a race and going next race, one of the top two Democratic firms, a firm called Doak and Shrum gave me a call and said they wanted to hire me to be an associate. So I moved to Washington DC where I ended up doing TV ads, speeches, debate prep and strategic advice for a number of races. You’re a consultant, you’re actually working a number of races, signing a bunch, hoping most of the win in the primary, if not all, then you have them for the general election. So I went from state to state to state doing ads, advice, debate, preps, speeches for different races.

Chitra Ragavan:   I just want to go back to when you were on your losing streak, what was that like to lose campaign after campaign in terms of your self-confidence and ego because those were high visibility losses, I’m sure. It’s not something you can hide when you’re losing a political campaign.

Jon Macks:   No. What you have to do is you still have to convince yourself to walk in the room like you’re worth a million dollars when you’re worth about 15 cents. Confidence to me is is something you project and that even in the worst of the races even when things were going bad, I would go in there and I would walk in and I’d say, “Listen, even though you have,” I wouldn’t say it, but even if a candidate had no money, little chance, I would say, “I know how to win this race. I’ve got the way to do it. Let me tell you and why you should trust me. It’s because the one thing to get you ready to win a big race is having lost a race. And I learned from losing,” is what I would tell them. So by the time I lost, I think, 23 straight, they must have thought I was the smartest consultant in political history.

Chitra Ragavan:   So how did you go from there to becoming a comedy writer and on Jay Leno’s Show?

Jon Macks:   When I was growing up I’d always been fascinated by two things. One was the Tonight Show and two was politics. And when I was in law school, I realized that you could basically go into the world of politics, which was a 300-night a year profession or you could go into stand-up comedy which is also about 300 nights a year. So I ended up basically choosing politics. The truth is I don’t think I’d have been a very good stand-up, but I ended up choosing politics. But I always had that bug to write comedy. And then one day I read in the Washington Post that was in the days when people actually read newspapers, I read in the post that Jay Leno was coming to a theater called Wolf Trap outside Washington DC. And I’m reading the article and it said that he book jokes from freelancers.

Jon Macks:   He had not yet been named to take over the Tonight Show. I ended up calling NBC, getting someone in Jay’s office who sent me a freelancer agreement. Now, what I didn’t know was there was 900 freelancers, and if I knew that I probably wouldn’t have sent in any jokes. But I thought, “Oh, they must think I’m really special.” And so I signed the agreement and sent in jokes and I started sending them in. Jay was guest-hosting one night a week and then later a whole week a month for Johnny Carson before they named him to take over. He started using jokes and then he called and said, “Hey, you want a job?” And I ended up thinking about it and there I was with three young kids and I was traveling.

Jon Macks:   I think that one year I think I had 270 flights. And I just made the decision we’ll let me try the comedy thing. But what I did is I told my partners in politics, I’ll be back in 13 weeks because it’s a 13-week contract, and there’s no guarantee that it would work. Well, I ended up staying with Jay for 22 years.

Chitra Ragavan:   So you weren’t very good at predicting things.

Jon Macks:   I’ve been completely wrong my entire life. Let me just tell you that. The line I always use is I’d rather be an effector than a predictor.

Chitra Ragavan:   Do you remember the first joke you sent to Jay Leno?

Jon Macks:   Oh, yeah. It was really stupid. When I say stupid, there’s two types of stupid jokes. Stupid as in stupid funny, that’s really a good joke or stupid as in it’s really not a very good joke. This was the latter. It was I think July of ’91 and there was a solar eclipse, total eclipse somewhere and the joke went something like: There was a total solar eclipse today that throws all the animals way off. The chicken stop clucking, the cow stop mooing, the hookers come in on Times Square. I was watching that night and watching TV, watching Jay and all of a sudden I heard the joke. I go, “Wow, he did a joke just like mine.” Then three days later that big check for $50 came which from where I’m sitting is still on the wall. Well, actually not the check. I actually wanted to frame the check until my wife told me, “That’s really stupid, cash the check, frame the second part to it,” which I did.

Chitra Ragavan:   What was it like to get that first check from from Leno for something that you just… It was like a throwaway thing for you at the time.

Jon Macks:   Yeah, it was a hobby. It was someone who is a great opera… Not a great… Someone who’s an opera singer who decides they want to go play baseball and end up getting hit. Oh, that’s really interesting. It’s a hobby. But as time went on, he used more and more and actually he called twice, he called first and I think January of ’92. It was right after we had our third kid, and he said, “I’m putting together my staff when I take over for Johnny, would you be interested?” And my belief is you always say yes. Yes, I’m all… Yes, you’re interested. You can always work out the details later. And then when he called back a month later and offered the job, it was like, “Okay, let me figure out how I can do both and from February…” Or actually from May ’92 until November until the election, I did both my political clients and Leno. I went back and forth, I was LA to Columbus, Ohio, to New York to South Carolina to South Dakota, all over doing both writing jokes on the way.

Chitra Ragavan:   Did you always know that you were destined to be a comedy writer? I mean, were you funny as a kid? Were your parents funny? What was your childhood like?

Jon Macks:   My parents were lovely and the least funny people that ever lived. There’s no other way about it. They were not funny. They were just normal parents. And I’ll never forget when I got the job with the Tonight Show and told my mom that I was going to go out with Jay Leno and worked there for 13 weeks, she said, “But you’re not funny.” I mean, my parents were inadvertently funny, especially my mom. And she would say things that were double entendres, but she thought it was a single non-sexual entendre and we all laughed hysterically. But with comedy and whatever, I just always loved comedy. I love comics. I love listening to them and that was I think the drive, in just listening to the greats is what made me want to try to be funny.

Chitra Ragavan:   Now, you had this very interesting nickname when you were young. You were called Icepick. What was that about?

Jon Macks:   Yeah. That was a little bit different. My dad was always perpetually either about to go bankrupt or losing a car. He had a business. He had a soda business, an ice business and a beer business. And what would happen is on the ice business, he had one of those ice machines which they don’t have anymore where he would put in 75 cents in change and it would spit out a ten-pound block of ice or ten pound bag of crushed ice.

Jon Macks:   And when I was eight years old, what would happen is it got very busy in the weekends especially in the summer. People buying ice for their picnics, whatever. This was in Philly. My parents would drop me off at 8:00 in the morning outside the ice machine. My dad would do deliveries. My mother would handle the business. And I would be sitting there from 8:00 a.m. until about 5:00 p.m., just me eight years old in a really rough neighborhood in Philly, to give change. So people would come up, they need change and I give it.

Jon Macks:   Well, one time I came up, robbed me, took the money. I was eight years old. So I came back and told my parents. And of course the first thing my dad did was get upset. “How’d you lose the money?” What was I supposed to do? So I said… I’m eight years old. Basically, what am I supposed to do? And their solutions were to give me an ice pick to stab whoever robbed me in the leg so that I can then run across, I can’t make this up, a four-lane highway to a car wash across the street where my dad would give them a case of beer once a week to look out for me on Sundays in case I was running wildly with a bleeding felon chasing me. After that I was Icepick Johnny for quite a while. Even at the age of eight, I never had to use it luckily, never had to use it.

Chitra Ragavan:   I guess that began your comedy career.

Jon Macks:   Yeah. Well, actually it’s interesting because what you do is when you’re a kid put in a situation where you have to deal with adults and a lot of them are drunk, and you’re eight and they’re 45-year old men generally in a rough neighborhood. You learn to use your wits. You learn to be able to talk your way into anything and out of it. And I think if there’s a way, that the genesis of where I learn to think funny or think fast came, it was probably in training that I don’t think my parents ever anticipated. They just wanted me to give change.

Chitra Ragavan:   So you were on Leno’s Show for 22 years and you were the only writer to stay with him for the entirety of his hosting career.

Jon Macks:   There was two. We started with eight writers, at times it went at 14, but for 22 years 4,610 shows there were two guys who made it the whole way. It’s a guy named John Romeo who’s from Chicago and me from Philly. I’m sure Romeo’s name was probably Icepick John back in Chicago too.

Chitra Ragavan:   And you came to be known as the joke machine, right? I mean, throw me some stats here. How many jokes did you write a day? Over 22 years, how many of them made it on the air? I think your set some major records.

Jon Macks:   Well, I mean here’s the thing. There’s some writers that will write 15 jokes in a day and 12 will be awesome. That’s not me. I deal in volume. And the only way I could really do it and that really did it, is maybe because I think fast whatever, maybe I don’t put enough time into each joke. So I ended up writing about a hundred jokes a day. Plus what I would write for bits and sketches. So we figured it out going back. I wrote about 500,000 jokes over the 22 years. And they did a count and I think there was 18,000 that got on, which somebody told me a couple people said that’s the all-time record. I guess if there’s someone that probably has some App that can figure it out.

Jon Macks:   But that means an optimist says, “Oh my god you got 18,000 jokes.” A pessimist would say, “That means 482,000 jokes got thrown away.” And that’s probably what drives you as a comedy writer. It’s how do I get on? And every night, if I had four jokes on a night it was a great night. Jay would do a monologue 23 to 32 jokes. So I’ve had four jokes on a great night. Three, Good night. Two, fair night. One, very depressed. None, I’d be suicidal. It’d be like hide the dog when I get home. And it averaged out because I remember one Monday I got 12 jokes on in a 22-joke monologue, and I think over 13, and that I think where they told was the record. And I thought I am pretty good. And the next three nights I didn’t get any on. So just it averages out.

Chitra Ragavan:   And what people may not know is that there’s a lot of competition to get your jokes on. I think I read in your book that Leno read at least a thousand jokes a day and so yours had to be good enough. And there were a bunch of writers, so yours had to be good enough to make it through that pile, through the day and on the air.

Jon Macks:   Right. And the one thing about Jay is there’s some shows where it gets cutthroat. Saturday Night Live has a reputation for people fighting. Jay cultivated an atmosphere that was just creative. You just turn in the jokes and let him pick. No one ever fought for their jokes. No one ever went in and said, “You didn’t do my joke.” And he never said… He is by the way the nicest guy in the world. He never said to anyone, “You got to do better.” It was, “Just keep them coming. Keep them coming, I’ll figure it out.” In fact the only thing he ever said that even was remotely, step it up, put it himself. One morning I came in and he said, “I’m a little light today,” as if it’s his fault that the jokes that we’ve sent aren’t good enough. And it made you want to…No one ever had to be told to write more in that show. Again, people wrote different amounts. Some wrote 20 or 30 a day. Some were like me, wrote a lot more. Like I said when I started, we had eight writers. At one point we had as many as 18.

Chitra Ragavan:  So it was pretty remarkable when you had one of those runs where you had three, four, or five jokes or even that day when you had 12 or 13.

Jon Macks:  Yeah. Like I said, you feel like you’re on top of the world and then you realize that the show is a monster that eats up material, that as good as it was on a Monday night, you still have to do your 100 jokes Tuesday. You still have to write sketches. And you know as soon as it’s done whether that Tuesday night show is good or bad, you come back Wednesday. And it’s five nights a week and it was 47 weeks a year.

Chitra Ragavan:   That’s pretty insane, and you make it seem so easy. What was your workflow, like your formula? I guess you start with newspapers first thing in the morning and reading all the stuff.

Jon Macks:   I would start with a bottle of gin. I would drain it then I would go to the edibles. But on day one I didn’t do that. There wasn’t edibles back then, it was old-fashioned. It was old-school. It was roll it up. But what I would do is this, on the way, I would get up, lay in bed for just 10 minutes or so and just think, okay, what are the stories from yesterday that can hold? Okay, then I get in the car, I listen to the radio, get into the office and then I would… And it was completely arbitrary, but it was just my system, layout nine different topics. Topics of the day.

Jon Macks:   And I’d look through the newspapers. So if it were today for example, we would say okay, impeachment is a topic and Thanksgiving is a topic, and the fact that the Cleveland Browns are good or bad as a topic, and the fact that Frozen 2 opened. So I write these topics down. Then I always try to write jokes connecting the topics, seeing if they worked, see if there was an association you could make. And you get 20 or 30 jokes out of that, then I’d really start going into the newspapers. This was again the Internet was when we started was obviously just starting, and I’d go to the newspapers. I’d read four or five.

Jon Macks:   And again, I’m not reading for depth, I’m reading for what’s the stupid story, what’s an interesting story. What’s something that people will get that we can make fun of.And then later on there was great websites like FARC and things like that. And there were the site aggregators where you can go and you can just look at the story quickly, see the headline and say, That’s something that I can make fun of. All of a sudden you’ve done 100 jokes.

Chitra Ragavan:   And what’s interesting is how you connect two seemingly, totally under a lot seemingly just totally unrelated topics, and then you give it a twist and that turns into a joke.

Jon Macks:   Yeah. I mean, right now if you were to do something like that because let’s assume it’s very cold, it’s an LA show, it actually is very cold today here in LA. You’d start out by, saying amazing day, freezing cold this morning, down to 32. It was so cold that Rudy Giuliani and the special prosecutor huddled for warmth. They’re called formula jokes, those, but they get you started so you can get to the smart jokes, the bigger jokes. Things like that.

Chitra Ragavan:   And in addition to writing for the Jay Leno Show you’ve written for 22 Academy Awards, you’ve written for the Golden Globes. You’ve written for the American Music Awards and you’ve written for comedy specials for Roasts, Presidential debates, and you’ve got different kind of frameworks, but different genre of each of those things?

Jon Macks:   Sure. First of all, I start with this. No climb too small, no feat too large. So if you start with that premise and you just say yes to everything, it makes it easy. I would say like a hooker or a taxi driver, everyone gets to ride. If you’re writing for example for an award show at the Academy Awards, whereas Jay is a topical monologue, and you’re reacting off the news, with the Oscars you’re… In other words, you’re going to be writing material about the movies of the year, about the show itself, about the nominees, it’s self-contained. If you’re writing for a comic, if you’re writing for their stand-up act, again, that’s then getting their voice. What is in their life? What is it their communicating?

Jon Macks:   And I call those you do jokes but you also have to think more thematically. If a comic is just going through a divorce, let’s talk about the divorce. What does it mean? How does it change? How does it change his or her life? So you really get the three different things. A topical monologue is one thing. An award show monologue is another. And then there is the writing for a stand-up comic which a lot of times don’t come obviously many of them with I want to talk about X. And then you can feed jokes that fit that thematic they’re already thinking about.

Chitra Ragavan:   You said in your book, Monologue there’s this big difference between like a late night show and the Oscars where with the late night show you’re trying out jokes on an untested audience before a few million people sitting on their couch, but with the Oscars you’ve got tens of millions of people and you’re trying out untested jokes on them. What kind of pressure does it put on you as the writer?

Jon Macks:   Well, me I just blame the other person who wrote it. There’s no pressure at all. But assuming that I have some kind of a little bit of pride left, the advantage of the Tonight Show and that is that even if a joke again on… Again, if you’re a stand-up, you’re taking your jokes out and testing them in the clubs twice a night, four nights a week, maybe more. Over the course it’s months in a year. So you’re testing. You know what’s working. If you’re a late-night host, again, you’re doing it for the first time, but you have that great advantages if it doesn’t work, you got to do it again, tomorrow night. The stress with the Oscars or any major award show is, it’s one shot. You don’t get to the next night, do the Academy Awards again.

Jon Macks:   You do it and it’s one shot. You’re hired for that year. You don’t have a long-term contract, so you really… I mean, the stress and the pressure is on the host, but for a little bit, for me as a writer, it’s you want to… You always want to bring your A-game, but I’ll call it the difference between a marathon and a sprint. The Tonight Show is a marathon, the Academy Awards are a sprint.

Chitra Ragavan:   And you’ve also learned to structure monologues differently based on a US versus international audience like the time you went to Israel to help Jay Leno do his act over there.

Jon Macks:   Yeah. Again, that goes to the larger thing of, “know your audience.” And this goes for whenever someone is in public, whenever someone is speaking. Whether you are a comic, whether you are a CEO, whether you’re giving a toast at a wedding. I always say for a bachelor party, I always tell the best man and said, whatever you think is funny is not. That private story of you and the bachelor about to get married in Vegas, not only does no one know, whenever a story somebody goes, “Well, you had to be there,” well, no, we’re not there. You have to know your audience. And so that’s the first thing.

Jon Macks:   When we got to Israel the jokes that Jay did had to be tailored to an audience that was probably 40% Israeli, probably 25% European and Russian, and part-American. So what’s the universal? What are the things that everyone can get? You have to make sure that everyone knows the topic because if you’re in Israel and you do a joke about Lindsay Lohan getting drunk the night before, they have no idea who Lindsay Lohan is half the audience. But if you do a joke about a politician in Israel who got arrested and the joke is universal, and there’s a great joke Jay did because there’s been I think four or five Israeli politicians that have been arrested recently, wrote for the show and he said, “When you ask an Israeli politician his cell number, it has a totally different new meaning.” And that applied everywhere. People in Israel knew it meant a particular person, but the Americans knew it meant just corrupt politician. So that’s the advantage there. So know your audience is my number one bit of advice for something.

Chitra Ragavan:   And you also learned something interesting about audience feedback and the applause on these live shows and sort of the feedback that you get, and how that relates to being able to predict the direction of polls during a political campaign for instance.

Jon Macks:   Yeah, it was interesting because I always said The Tonight Show audience was a nightly focus group of 400. This is the audience in the studio of 400, I’ll call real people. Do you know what I mean? In the sense of they weren’t show business professionals, they weren’t rich, it was a diverse crowd, but they were all middle-income people who work for a living and here was their trip to LA, and they’re getting to see a TV show.

Jon Macks:   So I would find they were ahead of the polls. So I’ll never forget it was probably… Geez, where was it? It was probably most July, August of 2008 and I’ve been helping out Barack Obama’s campaign through my friend David Axelrod. And I remember calling David one day and say, “When Jay starts to joke and he says Barack Obama, community organizer, people start to laugh before he gets to the actual joke,” that’s in the setup. So if they’re laughing at you before the joke, there’s a problem. And we started to see that over the next few weeks, Obama started to dip, not horrifically but two down, three down, four down.

Jon Macks:   And then I’ll never forget John McCain I think, it was September 15th, 2008, he made that comment about how the economy… Just when the economy was in horrible shape. He said, “Economy is in fundamentally good shape,” and people laughed out loud. And the next second you said John McCain’s name, before you even got… They would just start and go, “Well, Senator John McCain,” and people would start laughing. And I called Axe and I said, “It’s over. We’ve won. Don’t worry, we’re good.”

Jon Macks:   But the polls didn’t reflecte it for about a week. It takes a little time. People get it, audiences get it. And I say you can never convince an audience of something that they cannot believe. We cannot convince people right now that Prince Andrew is a good husband and a good father and a good person. We cannot do that. No matter what you say, I don’t care what he does for the rest of his life, we cannot convince them. He has become the joke and that’s the one thing about comedy. You want to be the set up in the joke, you don’t want to be the punchline.

Chitra Ragavan:   And you said so really interesting in your book which is that the recent stand-up comedy works and people trust what they hear when somebody like Jay Leno says something is that there is this… It’s true. There’s a there’s a truth behind it, and the audience may not loudly say it, but they are thinking it and when Jay Leno says it, it becomes something that they trust because they’ve already been thinking about it.

Jon Macks:   Yeah. There’s a couple of things. The premise in the monologues in late night are always true. In other words, we’re not making up the story. In other words, when we say that Donald Trump said X, we’re not making it up. So the premise is true. So right there, they’re actually getting a little bit of factual news. But also the idea, and especially when you build up trust like Jay did over the years, people understand that it’s there. There’s an old saying that “Country music is three chords and the truth.” Well, to me jokes, a good late night monologue joke is a true set up, a premise, a twist that’s believable and then the truth. One of my friends on The Tonight Show for years Wayne Kline once said, “All we ever do is rewrite the news.” And that’s a pretty good way of looking at it. Not the premise but the twist on it, the way to look at it.

Chitra Ragavan:   And you have this interesting way of describing it which is the comma. If you hear somebody’s name, comma and that defines them, then they’re in real trouble.

Jon Macks:   Yeah. Again, let’s go back. This is years before you were born, Chitra. You’re such a young person. But Dan Quayle, we think of as Dan Quayle, comma, stupid because he misspelled potato. When you think of Bill Clinton, unfortunately for many people they don’t think of best economy and peacetime, what did you hate more? The peace and the prosperity. You don’t think of a president who did all he said in a good way. Unfortunately you think, comma, affair. When you think of Donald Trump, let’s say that you’re a Trump supporter, which clearly I am not, but you’re not going to think Dow Jones 28,000, you’re going to think Donald Trump, impeachment query. You get that comment and it’s very hard to erase. So like I said if you go to Prince Andrew now, it’s not Prince Andrew, comma, member of Royal Family, it’s Prince Andrew, Jeffrey Epstein.

Chitra Ragavan:   How do you know what topics to stay away from or how not to go too far and even defining that like the Jeffrey Epstein story, there’s a lot of tragic consequences for women with these MeToo stories, but the Harvey Weinstein’s and Jeffrey Epstein’s of these world deserve to be skewered.

Jon Macks:   Right. Ricky Gervais who’s brilliant, and I’m a huge fan says, “The problem today is that people confuse the subject of the joke with the target of the joke.” If I’m doing a joke that has the words… With modern audiences, if I do a joke about Jeffrey Epstein or Prince Andrew or whatever, you automatically go, “Ooh, he’s talking about…” No, we’re about to hit the target of the joke, the target of the joke is the bad guy. Harvey Weinstein, Jeffrey Epstein, Prince Andrew. They’re the bad guys and people confuse it, so which is, my rule is, first of all, my rule used to be if the joke’s good, say it.

Jon Macks:   Now in a day of cancel culture, and people who looking to be outraged, sometimes I will tell a comic, “Look, this is a great joke. You laugh, I laugh. We know that five years ago, 10 years ago, this joke would not get to work, but someone’s going to be offended by it. Incorrectly offended by it. So is it worth it? And to be honest, that’s a problem because comedy is supposed to push boundaries. Comedies is supposed to break down barriers. Comedy is supposed to make you think.

Chitra Ragavan:   Although and we’re in this age of political correctness where it’s very, very easy to offend someone very quickly and to have it go viral on social media, and to even have yourself canceled so to speak in the halls of public opinion, and I think it was Chris Rock, you mentioned in your book has said, he doesn’t want to speak on college campuses because young people are so sensitive and politically correct today. And you’ve had a lot of comedians get in trouble over recent years. How do you-

Jon Macks:   Yeah. I mean, to me what I say is we’re not offending them, they’re being offended. The audiences today for many people are looking for the outrage. They’re looking for the… Wait, he said the word “race.” Sarah Silverman did a joke, a famous joke about rape years ago. Obviously, she’s a feminist and a strong woman. It was a joke. Do you know what I mean? Gilbert Gottfried is perhaps most famous because at the Roast with Hugh Hefner in 2001 in November he did a joke about a plane flying into the Empire State Building, and there was dead silence. And he rescued it by telling you a joke called the Aristocrats, which is they even made a movie about the event and whatever.

Jon Macks:   But today, unfortunately you have to know your audiences which is why if you’re a brilliant comic like a Chris Rock or maybe a Jerry Seinfeld, you don’t play to certain audiences because they’re not going to get the jokes and they’re going to be offended, and it’s not worth it. To me, honestly I say let the marketplace dictate. If you’re funny and you’re telling good jokes people will see you, and if your jokes are not funny and you’re not making people laugh and people are not seeing you, then you’re going to have to change your act.

Chitra Ragavan:   In addition to writing comedy, you’re also working as a political consultant advising even some on the current slate of Democratic presidential candidates. How do you prepare for something like that?

Jon Macks:   I’ve always been a political junkie. And so I’ve always followed the news. I actually think in a way that being a comedy writer has made me a better analyst of the political situation and better able to give advice because I’m not locked in that Beltway mentality. I’m not locked in the echo chamber of Washington DC, in the Beltway. As a comedy writer, you’re always looking at something with the question of what’s odd about this? What’s wrong about this? How can we poke fun of this? How can we poke a hole in it? And so I think it’s actually made it better. There’s actually one point I wanted to go back to about… And we’ll get back in a second about what we talked about was in terms of the jokes, and what can offend, I just always tell people who are listening and whatever is that if you think it’s a problem don’t say it.

Jon Macks:   And always remember that we don’t want to make fun of victims. You would never have… You always want to make it clear that we’re making fun not of Richard Jewell which is what everyone did in the Atlanta bombing in 1996, but we’re making fun of the bungling of the FBI. If this were happening today, you wouldn’t be making fun of Monica Lewinsky. You would have all your jokes trained on Bill Clinton and the establishment, and whatever. So again, the standards have changed in a good way for the better. I just wish the pendulum would swing a little bit back so people to understand that the target of the joke is who we’re really after, not the subject.

Chitra Ragavan:   And what’s it like working on current Democratic debates given this huge slate of candidates up on stage and you’ve just got another one added to it. I mean, how do you even convey any kind of lasting punch in our message with that massive presence on stage, different people?

Jon Macks:   It’s tough. I mean, the process they designed is silly. This is just me, but instead of having a three-hour debate with 12 candidates, how about two hour and a half debates with six. That’s just me. I don’t know if the math works, but it seems to me that everyone would then get their chance to shine in the sun more than the ridiculousness of seeing 12 people on stage. I mean it looks like… Now, I was going to use the word clown car, but my Democratic friends would be upset. But it’s ridiculous. This process could have been fixed very easily right up front, but they bought into it and I think it makes it very hard for some of the outstanding candidates out there to be heard. I’m always one for new voices, diverse voices, voices that have not been heard before, and I think that they have been stifled by the debate process. And that’s my 30-second political commercial right there.

Chitra Ragavan:   You’re looking at this Golden Age for political satire especially with President Donald Trump and impeachment, and all this stuff, and you’ve got this new generation of late night hosts. Can you evaluate how they are each approaching political satire, and their monologues, and their interviews?

Jon Macks:   It’s a lot different because when Johnny… We’d go back to Johnny Carson. Again, way before your time, but when Johnny Carson was there he really didn’t do political jokes. If he did, it was just an aside. Jay, he came up or he took over in the day of the 24-hour news cycle, and cable news so there’s a lot more stories, people are a lot more aware. But Democrats used to think Jay was Republican and Republicans think he was a Democrat because he would poke fun at both sides.

Jon Macks:   Somebody did a study and said he did 22,000 political jokes, 13,000 about Democrats and 9,000 about Republicans. And the reason, when you think about it for his 22 years a Democrat was president for 13 years and a Republican was president for nine. So it’s almost like he did a thousand jokes a year based on the party. It was mixed up all the time. And what you had then is I think people were more likely to watch the news and it was more you would have, I’d rather watch a show and people would watch it because you wanted to see what the comedy was not for their point of view politically.

Jon Macks:   We know what Stephen Colbert’s politics are. We know what Jimmy Kimmel’s are. We know what Bill Maher’s are. Now, Bill is of course interesting because he’s a libertarian contrarian. I’m a huge fan of Kimmel and I’m a huge fan of Bill, but you if you’re watching Samantha Bee, you’re watching Stephen Colbert, they’re really good at what they do, but why would you watch it if you were an independent or Republican? You’re not watching late night show, you’re watching a political thing. So it’s just totally different.

Chitra Ragavan:   One of the biggest game changers in this post 24-hour news cycle world is of late night shows with Jon Stewart, and you talked in your book about how polls showed that people trusted Stewart even more than network news anchors and that in general people trust the take of a Jay Leno or a Jon Stewart on the news more than the real news anchors. And that seems like such an indictment of the news business, but also a compliment to comedy writers like yourself. Why do you think there’s been this shift towards mistrust and cynicism of the news.

Jon Macks:   Yeah, it’s interesting. Again, the news was of course… There was three networks and it was you watched your news at night and you watched the anchor and that was that. And we would find sometimes they would make mistakes. What I think found is with the cynicism that came after September 11th for whatever reason, the nutty conspiracy theories that came out above that, Jon Stewart and Jay Leno were voices of, quote, “reason”. You turn to them… Especially Leno and Letterman after September 11, people turned to them. When there’s an earthquake, our ratings would go up in LA because people would want to see is it okay, what’s going on?

Jon Macks:   And I think however now, I would love to see a poll, well maybe there is one, I suspect that is before people didn’t trust the news, but they trusted their late night hosts, I suspect they don’t trust anybody now, which is why it would be so great to have someone who was a bit more independent there, more of Stewart. Again, Jon got more political as the day went on, but in the early years or the early years of the first half, he would pretty much just poke fun at whoever’s in charge, and that became a little more political as time went on.

Chitra Ragavan:  Looking back on your career, do you have any closing thoughts on this world that you’ve been in for the past 22 years and the role that monologue has played in your life and stand-up comedy?

Jon Macks:   Yeah. I wish I charged more. But my other closing thought, the true closing thought would be this, that all my life I wanted to, in a small way affect change, and originally I thought I could do that through politics. One enters politics very idealistically, one always does, no matter what side you’re on, you want to change the world for the better, you want to change it for your generation. And then at some point in my life I realized I was getting a little bit cynical, that maybe it was more of a business as much as I believe in certain candidates. So I thought it was time to make a move.

Jon Macks:   And maybe the way that I can affect change is in a world where we hear so many so much bad news where there’s so much tension, maybe… And again, I’m not elevating me, I’m talking about comedy, that the ability or the willingness to try and make people laugh and knowing that maybe in my case that maybe I gave someone in those 18,000 jokes at least eight laughs, if I could have done that then I’ve affected change in that person’s life for one day rather than perhaps changing the world like I’d originally hoped. And that’s not a bad way to go out, if that comes to that. That’s my thing, my closing thought.

Chitra Ragavan:   Well, thank you so much for joining me, Jon.

Jon Macks:   It was my pleasure. Loved it. You’re fantastic, and I’d love to do it again.

Chitra Ragavan:   Jon Macks is one of the greatest comedy writers of our time. Over 22 years as a writer on The Tonight Show with Jay Leno, Macks wrote 500,000 jokes, getting a record 18,000 on the air. He’s also a political consultant, awards show writer and has served on every Democratic presidential nominee prep team since 1996. Macks has written five books including his most recent, Monologue: What Makes America Laugh Before Bed.

Chitra Ragavan:   Thank you for listening to When It Mattered. Don’t forget to subscribe on Apple podcasts or your preferred podcast platform. And if you like the show, please rate it five stars, leave a review and do recommend it to your friends, family, and colleagues. When It Mattered is a weekly leadership podcast produced by Goodstory, an advisory firm helping technology startups find their narrative.

Chitra Ragavan:   For questions, comments, and transcripts, please visit our website at or send us an email at Our producer is Jeremy Corr, founder and CEO of Executive Podcasting Solutions. Our theme song is composed by Jack Yagerline. Join us next week for another edition of When It Mattered. I’ll see you then.