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. Tanscript Download the PDF 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 g...