To be perfectly clear: I worked on “The Jon Stewart Show.” The one featured in the sizzle reel above. (Made in order to convince publicists and managers that it was “safe” for their talent to appear on the show.) I did not work on the Daily Show. For reasons that will probably be clear to you after you read this.

The lessons I learned about creativity and leadership on that show revolve around humility,  openness to new ideas, and understanding the mission and task at hand. I was guilty of some major arrogance and hubris when I joined. It kept me from appreciating the new generation of writers, producers and performers there. It made me difficult to work with. 

Mostly, I learned that leadership is a privilege. By the time you get to a position of authority, you tend to think you’re special. You tend to think there’s some quality that got you to where you are. Yes, there is. But what got you to where you’re going will NOT keep you there or help you get further. Your team will do that. Start being grateful to them now, because if you do your job right, they’ll do theirs and all of you will move forward. They’re working for you, you are privileged to lead them.

Now, not only was I the wrong person for the job, the show was the wrong show for Jon. Paramount TV had just merged with Viacom and MTV Networks. The Paramount syndication people wanted a quick “win” to demonstrate Corporate Synergy. They chose MTV’s most engaging personality at the time, Jon Stewart, to host a late night TV show. 

I was coming off of Cheers, and knew the executive producers of Jon’s show from Late Night. At the time, Jon wanted to bring in a different head writer — Steve Higgins. He really should have been allowed to bring Steve in. Steve has been head writer for SNL for years and is well known to you as Jimmy Fallon’s announcer. 

But no! Paramount wanted a “grown-up” to help run what they saw as a team of “kids” from MTV. I knew MTV culture, knew Late Night, had just worked on In Living Color and Cheers. I looked like a good choice. (And in fairness to my agent at the time, he told me not to take the gig. What, me listen?!?!)

The world of syndicated television is REALLY hard. You’re essentially Willy Loman, selling your wares from small local station to small local station. You’re trying to thread the needle for a very specific audience. You have NO control over when the show runs or how the local station is promoting it. And you’re always trying to prove the ROI on your show versus a re-run of M*A*S*H. 

There’s not a lot of appetite for innovation, creativity, and risk in the world of syndicated TV. To be fair to the syndicated execs, they’re not exactly reaching an audience with a high tolerance for innovation and creativity. 

I came in as a barn-burning “let’s tear the place up” writer/producer. I wasn’t listening to anyone — I KNEW what Late Night TV needed! 

Here’s where I owe Jon and everyone a huge apology: I wasn’t listening to him, or to the writers, or to my fellow producers. I moved in, quickly filled a wall up with ideas, jammed scripts through. I hired friends that I felt could deliver.

In the process, I ignored some of the amazing talent that had been brought in around me: Higgins, Andrew Steele (executive at Funny or Die), Dave Attell. I turned down Brian Posehn! I thought twice before calling Louis C.K. (He stayed on Conan, btw.)  I rejected a list of writers I’m too ashamed to list here.

What a fool! 

And when things started to go south — and trust me, they went south quickly — I was temperamental and “artistic.”

Workplaces are like organisms. When a foreign body lodges in an organism, the cells work around it until they can expel it. First sign you’re in trouble in a workplace is that people are working around you. Meetings were held and they “forgot” to put me on the invite. There were “secret” meetings and meetings where the topic was “how can we work better together.” 

The walls in the office were insanely thin. On one side of my office were the executive producers. On the other side, the director. I could hear them talking about when they would fire me. One day I heard “We’ll just invite him in this afternoon, before rehearsal.” I went to the movies for three hours that afternoon. They were looking all over for me. I was a real asshole. 

Here are the lessons I learned:

  • LEADERSHIP IS A PRIVILEGE. I know, I said it already. It’s really worth repeating. My great regret is that I didn’t show the new writers the respect I now realize they deserved. I should have walked into that office every day humbly thanking everyone for allowing me to work with them.
  • LISTEN. SHUT UP. ( I KNOW! I KNOW! I was supposed to learn that with Norman Lear!) You have to listen to really find the mission and job at hand.  I don’t think any of us on the show ever found what the show was really meant to be, and I was no help. At least once a day, Jon would say “Why don’t I just stand up and do the monologue and talk about what’s going on in the news, and then bring on some guests?” Smart man, Jon Stewart.
  • BE OPEN TO NEW PERSPECTIVES. Bring in smart, competent people who understand the world differently. If you don’t understand their work, ask around. See what you’re not getting. 
  • RELATIONSHIPS ARE EVERYTHING. Okay — if you work as a creative there’s no better example of the old adage of “What goes around, comes around.” Let’s look at Jon’s circuitous route to the Daily Show. 
    • Jon’s syndicated show gets canceled. 
    • Letterman signs him to Worldwide Pants. Jon guests hosts the Tom Snyder show (after Late Night) from time to time and is rumored to be Dave’s replacement on Late Night. (Lorne takes over Late Night and puts Conan in that job.) 
    • Jon is offered the slot AFTER Late Night, which he turns down. 
    • Jon does a show for the BBC called “Where’s Elvis This Week?”
    • Madeleine Smithberg, the Exec Producer on the Jon Stewart show, creates a show for Comedy Central with Liz Winstead. It’s called “The Daily Show.” Craig Kilborne is the host. Kilborne replaces Tom Snyder. Madeleine Smithberg brings in Jon to host The Daily Show.

So there! Treat people well, be humble. Suit up, show up, and show ‘em what you got! 

And Leadership is a Privilege.


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