In 1998, I submitted for the
Late Show with David Letterman. My comedy packet caught the eye of an executive at Worldwide Pants named
Kate Adler. She invited me to CBS for a meeting — it remains the best meeting of my career. Adler was supportive, knowledgeable and funny.
Adler sent my submission to the head writer of the
Late Show,
Tim Long. He liked my stuff enough to want to do a phone interview. We spoke for a while, and he finished the call by saying "Your submission is really funny — all you'll have to do is meet [executive producer]
Rob Burnett and you're probably good to go." It looked like my lifelong dream of writing for David Letterman would be coming true.
Then Tim Long quit the
Late Show.
I believe Long went to
The Simpsons. A great career move for him, but it had a
butterfly effect on mine.
For a while, I ended up in
limbo. At some point, Adler from Worldwide Pants called and assured me that I'd be hearing from them again.
Months went by, and I didn't hear from anyone. It took so long, I forgot about the whole thing, drowning my sorrow in question writing for
Win Ben Stein's Money. But I finally got the call — the
Late Show's new head writer would like to interview me. In person. Shortly after, I received a plane ticket in the mail. I flew out to Manhattan where the show had booked me a room at
Le Parker Meridien. With a view of
Central Park.
The interview with the new head writer was the polar opposite of my meeting with Kate Adler. To say it went poorly is an understatement. I won't go into the details, but it wasn't really my fault. For years I considered calling Adler and letting her know what happened, but it seemed politically imprudent. It was over. The brass ring had slipped away.
Years later when I read that the head writer with whom I'd interviewed left the show, I called my then-agent at William Morris. "The people at Worldwide Pants liked me, Tim Long liked me... the only one who didn't like me is the guy who isn't there any more. Can I get another interview?" I asked him. My agent responded by saying, "I don't really know anyone over at the
Late Show." I blinked a few times and responded, "You should get an agent. I hear they're helpful at opening doors."
I'm not bitter that I missed my shot at writing for Dave. I think about it this way: When I was 12 or so and living in
Parsippany, New Jersey, I used to wait until my parents went to sleep and then sneak downstairs into the living room to watch
Late Night with David Letterman. I'd turn the volume way down so my parents wouldn't hear the TV. Consequently, in order to hear the jokes, I'd have to sit with my face right up against the television. Years of watching
Late Night centimeters away from the TV has probably made me sterile.
So the idea that someday I'd actually have a legitimate shot at that dream job is astounding. To be invited in to the upstairs offices of the Ed Sullivan Theater is enough.
Well, maybe
almost enough.
I still enter the Late Show's online Top Ten Contest from time to time. It's sort of like scratching my phantom comedy limb. Prior to this week, I'd made it on the list three times.
• I forget the first one.
• Top Ten Rejected Titles For "Brokeback Mountain." (#4)
• Top Ten Least Popular TV Shows (#7)
My rewards for winning were a
Late Show cap, a
Late Show t-shirt and a
Late Show mousepad.

This week I won a fourth time. For this most recent one, I was lucky enough to be picked for
#1.
The list was
Top Ten Punchlines to Dirty Pirate Jokes.
I wish I were being offered The Job instead of another t-shirt. But I'll settle for knowing that I can still make the list.