At first glance, Neal Brennan seems like the kind of guy who has his shit together. He’s funny, charming, and has enjoyed a 30-year career as a successful stand-up comedian, writer, and producer, working on everything from SNL to Netflix specials. But his journey through comedy hasn’t always been easy – and his confidence took a few hits along the way.

“The biggest lie I’ve ever told myself is that I wasn’t capable of existing or thriving on my own,” Neal reveals when we sit down with him in L.A. He shifts in his seat as he prepares to pull back the curtain. “Okay, back story…”

The 49-year-old comedian candidly explains how he found himself working on the door of a comedy club as a teenager, where he struck up a friendship with the one and only Dave Chappelle. They went on to collaborate on a handful of small comedy projects together that gained some traction (e.g. the 1998 stoner movie Half-Baked), but in 2003 came what would be the opportunity of a lifetime: co-writing Chappelle’s Show. It was an instant classic that blended cultural commentary with a comedy style that made you wheeze and wince, but it all fell apart when Chapelle retreated to South Africa for almost a decade to hide from the pressures of press coverage. As the brain can so cruelly do, Brennan told himself his success was only thanks to Chappelle and that he wouldn’t be able to cut it alone – a perception that nearly destroyed him.

To help battle the self-doubt, Neal says he kept a physical reminder of his talents and success.

“I had an index card in my pocket of funny things that I’d written or done, whether they were sketches on the show or lines or whatever – things that I’d done as a reminder that I had some worth. If I felt like I was drowning or sinking, I could look at this and call off the dogs in my mind.”

Thankfully, he powered through that low point and found continued success in the comedy world – including hosting multiple podcasts and creating a hit Netflix special, 3 Mics. He’s developed relationships with some of the most well-known faces in comedy along the way – but he’s still navigating what role they play in his life.

“Right now, I’m a bit on the fence about how much of life is a solo endeavor and how much is healthy to invest in people. I was spending a lot of time and energy on people who weren’t reciprocating. So now I’ve withdrawn from a bunch of them. I thought there’d be this hole where they were and there isn’t,” he says.

“You’ve got to tell on yourself.”

Neal Brennan

“There’s not a lot I can’t share. I knew from therapy, and I knew from 12-step groups, you’ve got to tell on yourself. So I didn’t mind saying in 3 Mics that I’m a star fucker because it’s probably the biggest character flaw I have. And I wanted to say it, so I’d stopped doing it.”

By the end of our interview, Neal has explored all angles of his past, generously reflecting on both success and trauma. He’s put his life experiences under a microscope for the world to see.

Seems like a daunting task for some – but Neal handles it like a pro: “I think questioning our perceptions and the stories we tell ourselves and each other makes it more bearable to be in your human experience.”

We interviewed Neal Brennan for Question Your Perception Box, a Big Think interview series created in partnership with Unlikely Collaborators. As a creative non-profit organization, they’re on a mission to help people challenge their perceptions and expand their thinking. Often that growth can start with just a single unlikely question that makes you rethink your convictions and adjust your vantage point. Watch Neal’s full interview above, and visit Perception Box to see more in this series. 

Words: Jamie Carson

NEAL BRENNAN: Challenge me. What's the biggest lie you've ever told yourself? How spicy do you want it?

Hi, I'm Neal Brennan, and I'm a comedian and I've worked in comedy for the last three decades. Seems like a lot, but it's true. Biggest lie I’ve ever told myself. That I wasn't capable of existing or thriving on my own. So back story.

Going to film school. Working in a comedy club. Only other guy my age is Dave Chappelle. He's 18. I'm 18. He's already a great comedian. I'm working at the comedy club just at the door. And I start kind of giving people what we call tags in comedy, like, “Hey, maybe say this, add this line, add that line,” whatever.

I did it with a lot of people, the ones with Dave worked. We write a couple things together, then me and Dave do The Chappelle show. Spectacularly successful and then implodes. I'm now 30. For lack of a better word like on the street. I had severe doubts about whether I could do it alone. I had an index card in my pocket of funny things that I'd written or done, whether they were sketches on the show or lines or whatever.

Of things that I'd done as a reminder that I had some worth. If I felt like I was drowning or sinking, I could look at this and call off the dogs in my mind.

Please send me another one. God. Thank you, God. Well, pretty powerful. Is there a voice in your head that tells you how bad you are? That says you're selfish, you're spoiled, you're stupid. Whose voice is that?

There is. It's Burgess Meredith, the guy who played Mickey in Rocky. Rocky Clip. I'm kidding. The negative self-talk was probably my father. My dad was an alcoholic and violent. So if you have a potent enough negative figure in your life, they can just plant a seed and the thing is self-sustaining. You end up believing that you don't deserve a decent inner monologue.

I've done a lot of stuff to deal with the inner voice, to deal with just not feeling good in my consciousness. In 1999, I started going to a 12 step program based around codependency. I started taking Zoloft. I was like, I don't want to dance, but I understand why someone would.

I tried transcranial magnetic stimulation. Ketamine, that was not helpful. And then ring the bell. Ayahuasca. I went from being an atheist to I believe I have a connection to a central creation force. And then 5-MeO-DMT. Bufo alvarius. It is widely considered the most potent psychedelic you can do. It lived up to the hype. I was so disoriented I thought I might have to kill myself.

But not from depression. It was from disorientation. Straight up, I had thoughts like, “Am I in God's imagination?” Too far out. Let's put it that way. What I endured was almost unbearable. But I was better in my body, felt better, funnier, kinder, more loving, more apt to fall in love than I'd ever been.

Neal, when have you let go of a deeply held conviction?

Right now, I'm. I'm a bit on the fence about how much of life is a solo endeavor and how much is healthy to invest in people. I was spending a lot of time and friends and energy on people who weren't reciprocating. So now I've withdrawn from a bunch of them. I thought there'd be this hole where they were and there isn't.

What do you feel like you're not allowed to share? There's not a lot at this point. There's not a lot I can't share. I knew from therapy and I knew from 12 step groups, you got to tell on yourself. So I didn't mind saying in Three Mics that I'm a star fucker because it's probably the biggest character flaw I have because I was obviously using that as like, well, how bad can I be if I just… give me some. And I wanted to say it so I'd stopped doing it.

I think the benefit of questioning our perceptions and the stories we tell ourselves and each other makes it more bearable to be in your human experience. I've heard quotes. My problem was I believed my own thoughts. If you just say maybe more often instead of like fuckin definitely, you might be a little better off.

Neal, what is your most consistent and greatest hope? You know the end of a movie, they don't really do that much anymore, but when the whole cast is hanging out at a party. I'm still hoping that there's some coronation. Where all my friends from forever are there and like, “Oh my God, it's so-and-so. We never expected him. And the dead dog. What are you doing here?”

I want my dad to be there. I want everyone to be better. Including me. Especially me. I want harmony, you know? I want, like, an old 1970s Coca-Cola commercial. I want all of humanity experiencing effortless kindness, righteousness, love, beauty, joy.