When Comedy and Industry Were Creative

This piece was written before my substack rebrand for my friend Jessica Pilot who worked on Stephen Colbert’s show. If you care about the behind the scenes for your favorite comedians and the inner workings of being an artist or book in 2026 you’ll still dig the piece. Rebrand piece coming later this week!

There have always been artists.

Brilliant, eccentric, iconoclasts, and oftentimes… troubled. We flounder in the real world, a step away from being imprisoned, then at the buzzer write a song that took the world by storm, and all was forgiven.

Artists are constantly walking a tightrope. Oscillating between creation and self destructive danger.

Then one day things changed.

God created agents! And managers! Publicists, and firms! There was marketing and consulting and some bullshit called branding! (Though that didn’t come till later.)

Essentially, there were people who did all the shit artists couldn’t! Which is pretty much everything besides making art.

We keep missing flights? They book the later one. We refuse to take money from fans? “Talk to my manager they handle money stuff.” Bit of a drug problem? Lisa in PR can spin it! Or better still, Lisa’s assistant can get you better untraceable drugs!

I, Jamie, can’t update my website, post on IG without somehow getting myself shadow banned, etc.

But Jamie, you can at least advertise yourself and your art right?!

Babe, I hate myself, of course I can’t advertise myself.

Having artists advertise themselves is like if Tropicana's spokesperson were allergic to oranges.

But then one day you have a team! And that team will do all that boring shit while you just create your little battered heart out.

Where did this odd breed of organized, seemingly normal, well raised group of people come from? We will never know. These are men and women who could have been lawyers or doctors but instead opted to sit backstage with a pacing clown who is wondering out loud why he can’t do his big fart closer on late night TV?

But here is what many of you may not know. Even the business side of art is creative.

Was creative.

They may dress better than us but these peoples jobs were to go to the dives and discover the undiscoverable. Take chances. Put all their chips on the reckless. They would hear a hook or a melody and go, “I don’t know why yet but that dude has something.”

One of my old managers discovered Ben Folds. He was on his way home and someone said there is some guy you should check out. It”s like, fun piano rock?

What the fuck is fun piano rock? Half way home he couldn’t get that stupid phrase out of his head, turned his MOTORCYCLE around, and found Ben Folds.

Someone booked Bill Hicks on David Letterman, Andy Kaufman in a wrestling ring, gave Joan Rivers a mic. Someone whose career depended on how much money Richard Pryor made sat on the side of the stage, probably chain smoking, as Pryor talked about freebasing crack.

THAT FUCKING RULES!

We know how artists have been stripped of their creativity and or livelihood. Slaves to the algorithm, monitored for clunky political statements that don’t align with the Trump administration. Audiences being trained to ADHD right by a video that doesn’t have a proper “hook.” in the first 2 seconds.

Art should never be on the fucking clock!!!! We became artists cause we have done enough drugs to not believe in clocks!

But what about the plight of bookers, producers, agents and managers?

It’s easy to make fun of the ones who take 10 percent.

We are the special ones! Jumping rail cars and journaling like Jack Kerouac. Doing acid in Vegas like Hunter. Doing anything like Patti Smith. Misunderstood vagabonds who were teleported to earth to create. To turn heartbreak into poetry, turn drunken emberessments into a 10 minute standup set, and take the worst thing that has ever fucking happened to us and make it into the most beautiful song you have ever heard.

The industry? Reductively….They are the suits. The ones who say, “don’t say that.” And “I’m on a zoom hit you back in 10.” right before you never hear from them again.

Smoke and money.

But gather round kids, there was a time when the industry were creative as well. Some (whispers) are still trying to be!

Those motherfuckers DISCOVERED US. Of course they were creative! Of course I’ll give you ten percent! You found me when I was living out of my car and snuck into a poetry night to do a standup rant against organized religion in New Mexico (true story!)

I am rambling and digressing all over the place because this shit breaks me.

Last week after Colbert’s last show my friend Jessica Pilot who booked the comedians for a long time on that show posted some pictures of comedians she found. They were playing random comedy clubs across the country. She helped them. Guided them to the perfect set like a sherpa. Then, she sat with. Sat with them moments before their lives changed forever. (TV credits used to matter more than TikTok dances btw). Specials used to matter. Storytelling used to matter. The industry used to matter.

The only thing going viral meant when I started comedy was, “don’t fuck that guy.”

Back in the day I was being considered for Letterman. The booker saw several shows of mine, and even brought me to the Ed Sullivan Theater to stand on the iconic stage.

That’s how it worked!

You would journey with these members of the industry. You prayed one would be walking by during one of your sets when you were crushing.

These bookers would spot us, monitor us, nurture us, and then eventually rescue us. That makes it sound like they were grooming us for trafficking or the CIA, but you get what I’m trying to say.

In fact! My current manager was the same guy who booked me for Conan over 10 years ago! Would anyone book me cause I am a safe bet? Have you ever looked at me and thought the word, profit?

FUCK NO. I did a rant about drone strikes on a show where the other guest was Kobe Bryant. We were both literally insane. But insane together. Two fucking artists swinging with everything we had. Just one of us happened to have good credit and health insurance.

When JP and I first met he didn’t have a job. It was at Edinburgh Fringe and he saw my weird show in a basement with 15 other people. After the show we drank pints and talked about our favorite Andy Kindler stories. This was a guy who just loved comedy. I was a guy who just loved comedy. And we just talked about fucking comedy. A year later he called me and he was booking my heroes show.

I’m not saying these bookers, managers, and agents don’t still love comedy. I’m saying this fucking monster tornado of content is swallowing their souls as much as it ours.

I have talked to bookers whose only job now is to look at how many followers someone has. No longer is it to take a chance on someone who is just fucking good but hasn’t been discovered yet.

Imagine discovering someone in a bar when they had nothing, putting your reputation on the line, and then being there with them when they headline Radio City? That’s not a suit, that is a badass artist mixed with a degenerate gambler. That’s rock and roll.

I don’t want to be another writer who just complains about things not being the way it used to be. So I’ll beg.

Artists - don’t cave. Keep making weird fucking art.

Industry - don’t cave. Keep taking weird fucking chances.

The only way we beat this is together. And if not, we always have crack. (I learned that from one of my heroes.)