Bob Dylan on Being Creative

If you sang “John Henry” as many times as me – “John Henry was a steel-driving man / Died with a hammer in his hand / John Henry said a man ain’t nothin’ but a man / Before I let that steam drill drive me down / I’ll die with that hammer in my hand.”

If you had sung that song as many times as I did, you’d have written “How many roads must a man walk down?” too.

Bob Dylan


Wow. What a great and rambly read.

John Roderick on Being Busy

“I spend hours everyday just trying to fill the increments of time between now and my inevitable death. It’s been 20 minutes since I had a cupcake. Propriety and dignity prohibit me from having another cupcake for 45 to 50 minutes. So I’ve got almost an hour here to kill.”

John Roderick

Last Word to Steven Colbert Every Night

“Squeeze out some sunshine.”

Steven Colbert’s Producer


His producer says it to him just before he goes through the curtain to start the show. It’s a good call to arms for me.

In listening to this chat, I couldn’t help but think about the writers’ job. I thought to myself: their job is not to make funny jokes about the news. It’s to write scripts.

Which made me wonder about if I’ve got my job right. Is my job to make podcast episodes and articles and courses? Is it up a level: to help people make progress on their business? Is it down a level: to write lede paragraphs and write anecdotes and find a quote and make a case and write a closing story and ask a final question and then to slam those all together into an article?

I have my hunches.


More from this interview

“The pitch is not just ‘this is the story, we think it’s interesting and here are the jokes,’ but also ‘what is your character’s take? What is his opinion of it?’ Because in this show feeling is first. When feeling is first whoever pays attention to the syntax of things will never fully kiss you. So my character has to kiss the news really hard, he’s very passionate. He’s not ironically detached, he’s passionately attached. It’s important if only because he’s talking about it.”

Mike Judge on Hunches

“I had a hunch that I could make something funny if I could just put it together.”

Mike Judge


This was his hunch before he knew how to animate, before the shorts he did that turned into Beavis & Butthead, before B&B saved MTV, before success of King of the Hill, before the uncanny Idiocracy or Office Space or…

It was a good hunch, Mike.

Patton Oswalt on Depression

“I want blues and pinks, I just want to avoid the blacks and reds. Because the red is when you’re manic and you’re burning everything up, the black is when you want to kill yourself. I don’t mind blues, I don’t mind pinks.”

Patton Oswalt


This episode went on the “listen to this yearly” list immediately. Excellent conversation. Some more quotes below.


“My depression and my ego are two things that I treat equally, just like this, where I go, ‘{gentle parent voice} Oh, here you go, what do you want now? Alright, ok, I’m not gonna give you that, but we’ll do this, how about that? Is that reasonable?” George Saunders said when you deny a fault in yourself you’ve made it ten times more powerful. AND now you have two faults: the fault you had and the lie you’re telling yourself about it.”


Advice for new comedians:

“I hope that you are given two gifts. First, I hope you have a few years of obscurity, where you get to go up and it doesn’t matter if you bomb or kill, cuz you get to develop a purely unique voice. And second, I hope you have one night of just absolute flame out disaster on stage so you can have that experience, wake up the next day and realize ‘Oh, the world didn’t end,’ and you lose that fear.

And there’s another piece of advice Andy Kindler gave me that I tell to every young comedian… Never ever ask another comedian to watch your act or give you advice because even if they give you great advice, and they have the best intentions, all it will do is make you more like them and make you less unique. Figure out on your own, even if you go down the worst side paths… you’re gonna feel like you’re wasting your time but you’re actually not. The wasted time doing something stupid is gonna pay off huge dividends later. ‘Holy shit, I went down some of the darkest fucking paths and I’m glad I did, cuz I know what it feels like to get easy, cheap laughs, and I know that that feeling is actually bad in the long run, so I go for the better stuff.'”


Patton’s advice to Joe Derosa:

“We were backstage at Caroline’s and it was at the time when all those celeb love shows were out. And I said, ‘Patton, i’m working on this bit: if you’re a person who wants to be on one of these celeb love shows, your heart’s gonna burst, yadda yadda,’ and it went on from there. And I said, ‘Patton, is this premise too much like a Bill Hicks joke?’ and he said, ‘I don’t think it’s too much like a Bill Hicks joke, but I don’t know why you’d want to do it. All you’re doing is going on stage and talking about something you already know you agree with. Where’s the exploration in that? What I try to do in every joke is I try to have the moment of discovery. So, how I would do that joke is I would say, I used to hate shows like Rock of Love and Flavor of Love because they just parade these whores around, THEN i realized, these shows are great because they teach us who we need to quarantine (or whatever).’ And I was, like, ‘Holy shit, that’s a hundred times better than the joke I was trying to write.’ Always look for the moment of discovery in the joke. Don’t just go linearly down the path, try to find the path where ‘well I thought this, but now I think this and then that led me to this, bla bla bla.'”


“You really can’t make fun of something unless you love it. Making fun of something you hate, it’s very limited, like, ‘I hate it, it’s stupid, here’s why.’ But you’re like, this thing… I kind of like it, and here’s why.”