When Patton Oswalt, one of the top comedians over the past several decades, was going through the worst experiences of his life this past year, he wrote an entire post about one joke Gary Gulman made. ONE JOKE.

Oswalt starts off:

“This is…so perfect.”

I like the pause in there. LIke there are no words so he had to notch himself down even though it doesn’t express exactly what he wants to say: … “so perfect”.

He analyzes Gary’s joke and why it’s so difficult to do a joke like this (nobody sees how the sausage is made, they only see the final joke after years of perfecting).

Patton closes with: “Thank you Gary Gulman. I know a lot of my shit’s gonna get angry these next four years, but it’s stuff like what Gary’s doing that reminds me I gotta make sure it’s funny first. Angry doesn’t change shit. Funny disarms the horde.”


Gary is one of the best in the world. And no matter what area of life you want to improve in, studying in detail someone who is among the best, will up your game.

It ups my game. I am infinitely frail. I fall apart at the slightest resistance. I sometimes can’t handle it. I sometimes can’t handle failing. I don’t always believe you learn from failure.

But studying the best, makes my brain feel good. Like it’s being nourished. And that often gives me the strength to persist.

For the past five months I’ve been going up on a stage 2-3 times a week and performing standup comedy in front of an audience.

Often the other performers are people who were on the Colbert Show the night before. Or just released an hour-long Netflix special.

So I have to up my game all the time. I want to be “one of them”. And I don’t want people in the audience to be able to tell that I’m different.

Plus, I get scared to death. I am honestly so scared I am about to cry every time I am about to go on stage. Even if I’m going on stage to perform just five minutes of jokes. Five minutes is an eternity.

What I realized, and will save for a future post, is that there are at least 20 or 30 (and probably much more) “micro-skills” that I could not have possibly imagined when trying to get better at standup comedy.

I’ve been public speaking for 20 years. Is it that different?


Which is why I had to have Gary Gulman on the podcast. One of the best in the world.

I said above “five minutes is an eternity”.

Gary told one joke on Conan in 2016 that lasted six minutes. One joke where (and I measured it) he gets laughs every ten to fifteen seconds throughout.

He uses every skill in the comic’s toolbox. And probably many more that I haven’t been able to understand yet.

I printed up the joke. I gave it to Gary. I said, “I want to analyze this joke word by word.”

The first thing he said is, “This almost depresses me”.

“How come?”

“It took years to write this joke. And the others that I came out with around then. It’s so hard. Sometimes I can’t’ even get up because it’s so hard to do this.”

What follows is one of my favorite podcasts. We cover his career, the techniques he learned and how he learned them.

We cover the depression and anxiety and fear that goes into building any career out of excellence. We cover the micro-skills.

No matter what you do in life, the one who masters all the master skills of your field of endeavor will be the one who rises to the top. How do you identify those skills? How do you master them?

And we analyze this joke. To see the joke, Google: “Youtube Gary Gulman Conan States”. It’s his 7/13/16 performance. Watch it first.

Here are some things I learned:



The whole joke is about the states and how they were abbreviated. Gary walks out on stage, “I just wanted to recommend a documentary to everyone and then I’m going to go.” Everyone laughs.

No one believes him. But he’s totally COMMITTED to the joke.

In the podcast he says, “I’m bragging, really. Because I know I have something in my pocket that I’ve polished so frequently over the years. Years and years have gone into this one joke. And I know they haven’t seen it. It’s almost like I’m say, ‘Wait till you get a load of me.’”

A lot of comedians just pander for a laugh, especially in the beginning. Yes, fart jokes work. But GREAT comedy is art.

Gary’s worked hard and he’s know it. This transcends more than just jokes. People won’t always know that what you have to offer is valuable to them. Until you show it.

That’s how Gary builds rapport with the audience. They sense the commitment. They are in for the ride.


Audiences are terrifying. And often they don’t know you.

Might be a business audience in a meeting. Might be a reader. Might be a listener or a crowd. Or a comedy club audience.

They have to like you. Johnny Carson has said that this is the most important skill for a comedian.


Watch Gary’s clip and see how he becomes naturally likeable to the audience. These are techniques that can be used in every situation.

But it’s also how you build up capital so now you can take chances, propose ideas they have never heard of, build rapport with each person listening to you, and perform the magic trick of transmitting what you see in your head, into the heads of all the listeners.

I didn’t realize this was such an important skill at first.

Again, I have another post about this. But, for me, the results were disastrous when I didn’t realize how important this was.


Gary uses movement. It’s almost like he’s acting out the joke.

He points to the sky, everyone’s eyes move up. They’re with him. They’re in the story. “I need to keep their attention during that time because it’s a lull,” he said.

You can’t just tell your joke. Or tell your story. Or tell your idea. Ideas, jokes, stories are three dimensional.

Gary takes his joke and turns it from a premise into a three dimensional world we are suddenly all living in.



Throughout my entire life, I’ve been abbreviating states.  I’ve never thought, “Oh so many states start with the same two letters.”

Who thinks of that?

“What were you doing when you first thought of that?” I asked him.

“I think the first time was when I was in 2nd grade and I got the arrow book of the states. I got it in 2nd grade but it must’ve been printed several years prior because the abbreviations was a new concept in this particular version of the Arrow Book of States. For whatever reason, I wanted to memorize the abbreviations. That’s when I noticed how difficult it was.”

Thirty years later, he turned that difficulty into a joke.

I notice this with comedians. They observe everything out of the ordinary.

Seinfeld once said that a regular person goes into Bar Mitzvah and says, “nice buffett”. A comedian will go in and say, “why is there pork?”

I’ve been working on a joke lately. The premise is that OJ Simpson made $2.7 million while he was in prison. The premise doesn’t have to be funny. Just quirky. The punchline can come after years of work. Not in my case but in the case of the best comedians, jokes, speakers, inventors.


This is unique to Gary. He’s able to draw out jokes for 6 minutes. I asked how he’s going to get down to writing the next 6 minute bit.

“It’s daunting,” he said.

“How do you deal with the anxiety?”

“I’ll say this, but it’s something that’s very personal to me. Hopefully it will help people. But I was in the hospital for a few nights because of my depression and anxiety. I was overwhelmed. It was a couple of months ago. I wasn’t suicidal. I just went to the emergency room and they admitted me and changed some medicines up, but it’s literally crippling.”

“Did that help? The combination of medicine and them talking?”

“Yeah…I’m in a better position now then I was then. I can function a little bit better and I’ve been able to get back on stage.”

He said he had a fear of performing. Which was amazing to me because he’s so good at it.

But I get it. I can’t go on stage without having a panic attack. And I know he’s been on stage 1000s of times.

It’s hard. But once you say, “This is too hard”, that’s when you have to do it to get better. And improvement never ends.

That’s why I wanted to learn from him.

It’s easy for a comedian to tell crude jokes. Gary brings you into new territory.

He told me that once he got a hold of the abbreviations joke, he held on. “I tried to strengthen it and lengthen it.”

We kept dissecting. I wanted to get deeper into the toolkit. How did he make the joke stronger?


He’s a few minutes into the joke. They’re talking about abbreviating the first state (Alabama). Alaska is next. But he had to take the audience away from the story.

Or they’d lose interest.

He sets the scene. The whole team of abbreviators is eating breakfast. And Gary says, “The omelette station had just been invented and was sweeping the nation.”

“I’ve always felt uncomfortable with the omelette station,” he told me. I never thought about it before.

Hidden truths surround us. Ghosts in a conversation. But saying them brings the discomfort into comfort. Makes the scary…funny. Or possible. Or gives us a new way of looking at things.

“The omelette chef must hate us,” he said.

And in the joke Gary says they wanted to be a “chef chef.” Not an omelette chef.

The tangent diverts your attention away from the main plot. He adds another about the people who call Hollandaise sauce “holiday sauce.” This has nothing to do with the joke. But it’s funny and adds depth to the story. And does it have to do with the joke..? Maybe!

And then brings it back to abbreviations. Alaska is right after Alabama.

Both are AL. That’s when the “crack team of abbreviators” realize they’re in trouble. “Did we already use AL?”


In one of his first lines, Gary tells you the documentary is 98 minutes. Not 90, not an hour. It’s 98 minutes.

“Why 98?” I said.

It had to do with the number of syllables. And the exactness. Words don’t tell a story. Details tell a story.

And it ends on a “t”. Gary knows from 20 years experience what consonants will elicit a bigger laugh.



The crack squad of abbreviations is made up of “nayer do wells.”

I didn’t even know what that meant. “I like to use language that you forgot you knew,” he said.


Gary quoted the late Richard Jeni, who said, “What you’re trying to do is put together as many laugh lines as close together as possible.”

You don’t have to wait long to laugh again when you watch his act. Gary does this too. He makes a small reference.

“I want to say it was 1973… So I will.”

And the whole crowd laughs. At first, I couldn’t figure out why I was laughing. “It’s a cliche,” Gary said. He uses a cliche to make fun of cliches.

He makes you take a second look at some statement everyone says, but no one realizes they’re saying.


The joke gets more and more ridiculous with each line. But Gary looks almost clueless. He’s going on and on about this documentary, their struggles and challenges.

It’s almost like he crosses this invisible line where he’s no longer aware. He becomes part of the story.

And his comedy turns from joke to performance.

Everyone in the audience begins to see there’s no real documentary. Except Gary.

He subtracts self-knowledge which adds to the laughter. Because now people not only can’t believe how ridiculous this documentary’s premise is, but they can’t believe how ridiculous Gary is.

Adding knowledge makes a hero. Subtracting knowledge makes comedy.

James Bond can get shot in the heart, perform surgery on himself, and then get the bad guy. He’s a hero.

If Woody Allen is shot in the heart then….even picturing it makes me laugh.


Gary makes jokes out of difficulties, adds specificity, tangents, cliches and so on.

He has his tool kit. Each element has a purpose. And they all take him to the edge.

“That’s one of the reasons I’m moving to Boston,” he said. “I can take more risks.”

“What does it mean to take more risks?” I said.

“Just to go on stage with material that is not as worked out as the one we went over today.”

He wants to test his joke in front of audiences, then record it and tweak it.

If you can’t take risks, you won’t hit the edge. You won’t go beyond it.

Beyond the edge is peak performance. The area few, if any, hit.
Beyond the edge is success. Because people reward the ones who have mastered the risks beyond the edge.

I always say I don’t like to hit “publish” on an article until I’m afraid of what people will think.

That’s not quite true for this article. I’m proud to say Gary is one of the best there is. I’m happy I got a chance to take my absolute favorite joke and get the guy who told it to answer all my questions for an hour.

I felt bad when Gary expressed his depression. His desire to continually improve and his fear of where that next improvement might come from.

We’re all afraid.

I wanted to tell him…sometimes when I feel that way, and I feel that way almost every day, I often know that something new is going to happen. Something that will push me forward.

Afterwards, I felt bad I didn’t say that. I wanted to tell him how skilled he is. That he will push forward.

But I didn’t say that either. I’m hitting publish here not because I’m afraid. But because I want everyone else to experience the pure joy I felt when I listened to this joke, listened to how he crafted it, and learned a bit more about how in any area of life I can strive to improve and be the best I can be.