Announcing my directorial debut "The Comedy Hour"

Who the heck am I to make a movie?

Oct 24, 2025

Avid readers may recall a few weeks ago me coyly writing that someone had proposed an exciting idea to me but I wasn’t allowed to talk about it. Well, announcing the movie was that exciting idea.

Cat’s out of the bag. We’re making a movie!

This week we announced my directorial debut entitled “The Comedy Hour.”

We have attached Tim Heidecker, a brilliant actor, comedian, and all around artist. We have attached Tatiana Maslany, a generational talent, and also She-Hulk. And I have a team of incredible producers helping to shepherd along this insane endeavor. Hi guys!

Who the heck am I to make a movie?

I don’t think this is one of those self-doubt, imposter syndrome questions. It is a very valid question! It’s one that frequently comes up for artists, especially when they are making a first project or a bigger project than they’ve made before. And it is absolutely what your investors are going to be asking, every single time

So it is very worth asking yourself the question, and knowing the answer.

I don’t usually start with “why,” even though I recommend it (do as I say, not as I do).

I usually start with a crazy idea, and then spend a lot of time thinking about it, shading it in, and then eventually I’ll sit back and wonder… “Why this movie?” “Why now?” And in this particular instance — in which I’m directing the movie — “Why me?”

But what I have come to learn over the past decade (!) in Hollywood is that “Why me” is actually THE MOST IMPORTANT part of pitching a project to people. While everyone wants to make smart investments, and while we may like to imagine “it’s all about the story,” it’s not. Not really.

At the end of the day people want to invest in one thing: You.

If you can make them see you as a good investment, by having a compelling answer to “Why me?” you will get people excited and on board. It will happen.

As The Comedy Hour team and I have talked about “Why this movie?” “Why now?” “Why me?” it has become eminently clear that even though I started writing it thinking “well this is just a fun idea…” I was writing it from a deeply personal place.

Somehow I always trick myself into thinking “this is just fun!” only to discover after a year of pouring myself into something “oh this is actually about a deeply emotional issue of mine specifically…” How this somehow surprises me over and over again is something for me to talk about in therapy, not here!

I don’t want to say too much about the movie itself, because… why spoil it? But what I do think we can and should talk about is…

WHY THIS MOVIE? WHY ME? WHY NOW?

Let’s talk about MY JOURNEY TO THIS MOVIE.

*Here I am standing in on the set of Late Night, circa 2010.*

I grew up adoring late night television. As soon as I knew that there were people who wrote anything, I wanted to write and make late night TV. Any chance I got I’d stay up late enough to watch Conan or Letterman. Making something silly felt like a very important calling.

While I was in college in New York, I wanted to intern at one of these late night TV places. In New York at the time that meant: SNL or The Daily Show or The Colbert Report. I was lucky enough to land an internship at The Daily Show with Jon Stewart. This is back in the Jon 1.0 days, when it felt like the show had somehow cracked the formula for “comedy with purpose.”

[My opinion about whether this kind of topical humor is politically meaningful anymore has changed, but at the time it weirdly felt like what we were doing was… important?]

It was an incredible gig, that taught me so much, introduced me to some lifelong friends, and ultimately got me my first PAID JOB in entertainment. Working overnight by myself at the Comedy Central HQ. Weird gig!

But before I got that paid job, I landed another internship. This time for NBC, for the brand new Late Night with Jimmy Fallon. This production office was located in the hallowed halls of 30 Rockefeller Plaza, which, at the time, were also the hallowed halls of General Electric, a very boring electricity company. GE no longer owns NBC but during my tenure there I remember a lot of corporate GE training being required… Fun!

This show felt less… “important.” Jimmy has established himself now as being all about fun! And not about… politics. No comment!

I quit this internship. To go produce a micro budget feature film. And when I told my supervisor I was going to leave, I was told “you’re making a huge mistake.” Only time will tell if this decision in 2010 was in fact a huge mistake. Jury is still out!

Yes, I am now a working TV writer — hello from my office — but I did not return to television for a very long time after late night. I made non-profit theater with friends, and wrote films.

I was exclusively writing for other people, despite knowing that ultimately I wanted to do was go direct my own movie. I just didn’t feel ready.

The longer I worked, the more people I worked with, the more confident I felt that I knew enough to be able to pull it off. I just had to write something that made sense for me (and only me) to direct.

As I worked to figure out what a good first feature film would be for me as a writer/director… I thought about late night television. I thought about how much I love it and how pointless the format feels in our current world. It feels almost criminal to sit around and make up stories every day (and yet it’s what I do!) and it feels even more insane to do that with the express purpose of having celebrities on to talk about their upcoming projects and new business ventures.

So I wrote a movie about all that. And how that feeling seems to have seeped into every single aspect of our lives and work and culture.

We haven’t made the movie yet but we’re getting ready. I am so beyond excited.

And I cannot wait to share the journey of making the film with all of you as we continue to do it. The entire point of this newsletter is to get to show you how it all works (and doesn’t work!) as it happens. So here we are!

It’s silly but to be in Deadline as a writer/director is exciting. It’s a lifelong dream!

And it’s cool that a lot of other outlets picked it up from there.

It seems like there is definitely an appetite for this deranged film we’re going to make, and I look forward to willing it into existence, certain that I am the only person in the world who could make this stupid stupid stupid movie.

If you are into seeing this film, please, like this post! Share this post! And follow me on either Instagram or TikTok.

All of these metrics, as stupid as they are, do help get things made, and released. And they definitely help promote the film, later.

Which I am sure I will be writing all about here, when the time comes. But first, we have a lot of other work to do.

And with that, I should go do it!

Talk soon,

Colby

PS: Also yes this movie is a dystopian parable that features a singing robot. I should’ve mentioned that sooner.

PPS: We have a Hollyweird Hang (available for PAID HOLLYWEIRD SUBSCRIBERS) coming up next weekend, Saturday November 1st at 1PM PT. If you want to hang with us digitally, I’d love to hear what you’re up to, and talk about Why You. I’ll send out a zoom link to paid subscribers closer to the date.

If you aren’t a paid Hollyweird subscriber but want to be here’s the link to subscribe.

If you are a student / someone who can’t afford a paid newsletter right now, message me and I will comp you a paid subscription, no questions asked.

As always — comments and questions encouraged!