Drinks With ‘Crazy Good’ Comedian Neal Brennan

Neal Brennan has been a force in comedy for over three decades with both his own standup performances as well as working behind the scenes as co-creator of Chappelle's Show and writing, producing and directing with other comedians like Chris Rock, Amy Schumer and Seth Meyers. I spoke with Brennan about his new Netflix special ‘Crazy Good,’ his ‘Blocks’ podcast, the place of AI in comedy and whether billionaires can still be funny.

You used AI to generate some opening lines for your new special. What are your hopes, dreams and fears about AI and comedy?

I would like to be able to load all my material into an AI and have things generated passively for me that I can use (laughs). But I don't think you're going be able to replicate it completely. Human beings like human beings. I'm hoping it'll be incredible for medicine, scientific breakthroughs and automation. But in terms of an AI comedian — you're not going to root for the person. I don't think you want to see a new hour from me made in conjunction with a robot (laughs).

But you think it can be a tool?

If I can take what I've made and have AI farm material for me, yeah. I think Drake should be able to load in all his vocals and then if he likes something he can redo it. That is a fair usage artistically. But as someone who's written jokes for other people — I can get into the psychology of another person. I've written material for Dave Chappelle. What it took for me to be able to do that I don't think would be easy for a computer to do.

(Laughs) Does doing this interview entitle me to four more free articles at Forbes for the month?

Do you read publications like Forbes? They say athletes should take financial classes so they don’t get taken advantage of. Do comedians need that as well?

I don't know if you've looked it up but the top comedians make as much as the top athletes. I think Kevin Hart told me when he is going be a billionaire. I don't remember when it is but I know it's happening.

Does he have the date in his calendar? Like on April 6^th come to my ‘I’m a Billionaire’ party?

I think he does. I was talking about this the other day. I don't need to have more money than everyone, I just want to have enough money for me. You can only eat three meals a day. You can only wear two pairs of pants a week tops. It just seems silly. Also everyone hates rich people.

Would it alienate comedy audiences if they realized how much money some performers were making?

It's a weird thing. There’s a lot of big earners. I don't think people really associate it with comedy. But it doesn't really matter how much money you have if you can still bomb (laughs) — and the audience is aware of that. I also think charisma can make them forget.

What’s your drink of choice?

It's embarrassing. I drink Corona, okay? And a Corona and a half per month is about my drinking cadence.

The half is how it averages out or you just don’t finish a bottle?

Yeah, I just don't finish. I was lucky enough to direct a round of commercials for Corona with Andy Sandberg and Snoop. I got to scout the beaches for that. That was a weird dream come true.

Are you a beach person?

I am kind of a beach person. Like on your birthday you get a birthday cake and when you do good you go to the beach (laughs). I'm fair skinned and I have my skin cancer joke in my new Netflix special. But I don't really know what to do there. I just read, I guess. But the beach we scouted that I ended up using is the nicest place I've ever been on Earth.

Where was it?

It's on the island of Vieques, off of Puerto Rico. Looking out at the water, it's perfectly blue. The sand is very white. And it was 85 degrees, which is great for me. There was a nice breeze. It was just so perfect. The water is warm. And there were rocks on either end.(Laughs) It was like a bit of a cove, but not like too much of a cove.

It had that perfect balance of cove.

There's nothing more boring than nature description (laughs). Whenever there's a nature description in a book I'm just like oh God, plot point please. Somebody make this interesting.

Do you enjoy traveling?

I do like traveling. I like walking around big cities. Putting my bag down, putting on shoes and then walking for 10 miles. Tokyo is a great walking city. Singapore. London. Paris. Now I'm just naming cities.

On your ‘Blocks’ podcast you get comedians to open up about some of their deeper problems. Which guests have surprised you with what they’ve shared?

David Letterman was probably more revealing than he normally is. He's from a generation that doesn't really talk about things like that. All of their fathers were in World War II. I think the world is getting a little more open to mental health.

The most recent one that sticks with me is Bill Burr. He grew up in a pretty rough situation and we were talking about what it does to you. And Burr said ‘yeah, I often think who was I supposed to be?’ Which for a hilariously contrarian comedian, that's really kind of beautiful thing to say.

You have your own stand up, but also do a lot of writing and directing for others. Is there one side you prefer?

I got into comedy for the group dynamic, you know?The camaraderie. I always say I was hoping we'd all sleep in bunk beds.

There’s been a trend in comedy specials of adding things in with editing — words, photos, video — that aren’t truly part of the performance. What are your feelings about it?

I've been complimented for it and I've been told it takes people out of it. If I can do it in a way that adds a layer to the joke, like when I say like “why pray to a Jew when you can be one” and then we added Jesus popping out of the water. It's timed funny. So I understand some people don’t like it but the thing I always say is I'm competing with every single thing that's ever been filmed on Earth. I'm competing with ‘The Godfather,’ and the Olympics. and the Kennedy assassination and porn (laughs)! So forgive me if I try to do a little something with the video.