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The restaurant was closing up. I was sitting with Jackie “The Jokeman” Martling. Doing a live interview.

He’s been joke-writing for 40 years. 18 were for “The Howard Stern Show.”

“Could you be any louder!” he yelled at the wait staff.

Then he told the crowd to f*** off.

He told me about the early days of comedy. With Eddie Murphy, Rodney Dangerfield, Jerry Seinfeld. “They all got big,” he said. “I’m sitting here talking to you.”

It was his 3rd insult.

In one hour.

“That’s not insulting you!” he said. “That’s insulting me.”

“Ok, we’re even.”

Jackie has a new documentary coming out. It’s in production. And he also wrote the book, “The Joke Man: Bow to Stern”

“What’s the title of the documentary?” I asked.

“I don’t know yet,” he said.

It’s a work in progress.

Like everything he’s done.

“What’s really wacky is if you look at my life and connect the dots backwards, it makes perfect sense. It looks like I had a plan. And knew exactly what I was doing. And where I was going.”

But it wasn’t that way.

“It was absolutely haphazard,” he said. “The best description of my life’s pattern is a pinball. Bing bing bing. I just did the next thing I had to do because I had to do it. And the main thing you find out in life is that luck is a huge part of it, but really favors the prepared.”
I wanted to know more about how Jackie became one of “the prepared.” And how you can too.

You’ll hear how he quit his job at 30. Changed lives. Found his way in to one of the most competitive and brutal industries.
And still, at age 71, battles insecurity, imposter syndrome and the fear of losing what he’s built. Just like the everyman.

  • Special announcement: I’m giving my latest book away to my podcast listers. It’s totally free. Go listen at [0:00]
  • Episode preview [2:55]
  • I invite Jackie Martling onto the stage and talk to the audience – [4:20]
  • Jackie announces his upcoming documentary – [6:11]
  • Jackie and I talk about how to find your own path in life – [7:17]
  • Battling insecurity (how comedy’s great’s do it)- [8:50]
  • Why Jackie quit music at age 30 to become a joke writer and comedian – [10:00]
  • The story of how Jackie met Eddie Murphy when he was just getting started – [12:02]
  • The importance of doing what comes natural to you – [13:04]
  • I ask Jackie about writing for Rodney Dangerfield and what made his persona popular – [14:13]
  • The power of awareness… find out what really made Rodney Dangerfield explode – [16:22]
  • How fame today has changed drastically – [18:19]
  • Get ready to laugh… Jackie says “the worst Rodney Dangerfield story I ever heard.” – [19:45]
  • About the time I interview Rodney Dangerfield – [21:41]
  • Hear Jackie’s “best Rodney story” – [22:33]
  • I ask Jackie to tell us a joke he sold Rodney – [25:54]
  • Behind the scenes & the ugliness of Hollywood – [27:27]
  • Be yourself… proof that there’s no standard personality for success – [28:28]
  • Find where you belong… Jackie says why he can’t envision himself in any other industry – [30:30]
  • How Jackie realized he had to give up music to become successful – [31:14]
  • The power of free: Jackie worked for Howard Stern once a week for three years – [32:13]
  • What makes Howard Stern amazing at interviewing – [33:50]
  • What collaboration looks like – [34:15]
  • How to build better teams (spoiler: be abundant in the value you give) – [36:16]
  • The real reason why Jackie left The Howard Stern Show – [38:00]
  • Jackie The Jokeman Martling on “the essence of a joke” and the individuality of humor – [41:15]
  • What nuns think of Jackie’s dirty jokes – [41:44]
  • “If you’re not nervous before you do your show, you’re in the wrong business.” – [42:08]
  • Paul McCartney’s run-in with Jackie Martling – [43:21]
  • Jackie’s memories on “The Aristocrats” – [47:30]
  • I describe the premise of “The Aristocrats” movie and joke – [50:25]
  • The funny story of why Mark Cuban owe Jackie a favor (and how he’s repaying him) – [51:17]
  • The early days of comedy… working with Eddie Murphy, Gilbert Gottfried and Jerry Seinfeld – [55:07]
  • Hear Jackie insult me for the 3rd time in one hour – [58:19]
  • Comedians and sex changes – [58:41]
  • Jackie shares another nostalgic story – [59:21]
  • Wrap. I thank Jackie for coming on and he tells me why this was bull**** in true Jackie Martling fashion – [1:00:35]

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