There are things that are so hard to talk about, like the dubious proposition of becoming a parent; deep, immovable depression; the tenuous relationship between the races; and then you think about comedy and somebody like Neal Brennan, who, as many people know, co-created what is considered to be the best sketch comedy show in the history of television-- "Chappelle's Show."

But he's also directed and produced Amy Schumer and Chris Rock.

And for at least 10 years now, he's been taking the stage himself with standup specials like "3 Mics" and "Blocks," in which he talks about the very things that make the rest of us so uncomfortable.

I'm Kelly Corrigan, this is "Tell Me More," and today, I'm having tea with writer and director and groundbreaking standup Neal Brennan.

♪ Kelly: Hi.

Neal: Kelly, Please.

My car is broken down.

I--I-- Come here.

Do you have a gas tank?

Yeah.

I--I--please.

One step at a-- Kelly, shut the door.

[Laughs] [Door closes] ♪ So, we have something small but important and somewhat telling in common.

You ready?

[Laughs] We're both public figures who occasionally cut our own hair.

First of all, I'm a public figure?

You are.

Great.

You do things on stage.

I cut these.

How do they look?

I know.

A little bit of a mistake, right?

And now it's like I'm trying to be young.

Just give in to it.

Bangs are kind of a big thing.

What happened?

[Laughs] You wrote a ton and you co-created and co-wrote and co-produced what people who know think is the best sketch comedy show of all time.

Boy, do those people know.

Ha ha ha!

Man, oh, man, are they right.

What made that partnership with Dave Chappelle work?

Why was it so productive?

I think it was like a shared ethos of, first of all, like, what's quality, what's funny, and a shared-- a sense of injustice that we thought we could overturn via sketches and be like, people will see this and then the world will change.

He's actually said he's never met someone more obsessed with fairness than me.

Interesting.

Like, I'm obsessed with fairness.

Dave gave me a career.

We met in 1992 at a comedy club in New York City.

We wrote a few jokes together over the years, but I'd always hoped we could do something bigger.

Then in 1997, Dave calls me and goes, "Hey, if Universal reaches out to you, tell them we're writing a weed movie together."

[Laughter] And I was like, "What weed movie?"

And Dave said, "Don't worry about it."

[Laughter] Next thing I know, someone from Universal calls me and asks, "Are you writing a weed movie with Dave Chappelle?"

And I was like, "Yes."

[Laughter] And they go, "When can you pitch it to us?"

And I was like, "In 30 days' time."

[Laughter] So, we had a month to figure the pitch out, and finally on day 29, I called Dave and I'm like, "Dude, we got to work this weed movie out."

[Laughter] And he goes, "What weed movie?"

[Laughter] What's your favorite skit from "Chappelle's Show"?

It's a sketch called "Jury Selection," where Dave has to--it's like why he couldn't have been on juries like O.J.

and R. Kelly and Michael Jackson.

And it's funny--it's like when we were doing it, we were both like, "Oh, that's a good sketch."

And then as time has gone on, we've both been like-- independently been like, "That was the one."

The way it came about was, like, we needed a sketch badly.

Like, we--it was hand to mouth.

We had to do 13 shows in a row, 13 weeks in a row, so, there was no hiatus.

There was no, like, once we started.

So, that was like-- we were-- our backs were against the wall.

And there was a Michael Jackson article in "Vanity Fair," like the first really damning one, and I was like, "Here, I think it's-- That your wheels turn.

And then he started going, like, "No, no, no, no, no."

And I was like, we both like, "Ahh, let's go."

Like we--yeah.

So, that was-- it's rare that there's, like, a "Eureka!"

moment and--but that was kind of a "Eureka."

You're one of 10 kids.

You're the youngest of 10 kids.

Yes.

Who in that melee of people was, like, your person?

Like, who looked out for you?

I had a lot of them, actually.

I'll tell you who wasn't.

I'm kidding.

Let's start with who wasn't.

I'm gonna grade them.

Ha!

I think they'll love that.

Because, you know, 10 kids is too many kids.

My older brothers and sisters had to--not had to intervene, but they were all very generous with their time.

My brother Kevin, my brother Tommy were very big.

My sisters Mary and Anne were very, uh, you know, sweet and generous with their time as well.

Tommy worked in Chicago at the Chicago Stadium and Wrigley Field, so, I would go to, like, I probably went to 100 Cubs games without a ticket.

Just would walk in and I knew all the ushers.

And so, that was great.

And then Kevin's a comedian, so, I--in high school, I used to come to New York and be around comedy and comedians.

Yeah.

And you were working at a comedy club?

I ended up, yeah, kind of via Kevin and this guy Jason Steinberg and Barry Katz.

I worked the door at a comedy club.

Because you're imposing.

You're an imposing figure.

So, you were working security at the door?

I'm pretty-- yeah, I was even-- I think I might have been lighter than I am now.

So, yeah, it was-- I was a barker trying to get people in, and they used to call me "No-show Neal," [Laughs] Because I wasn't--people-- people were not buying it.

What were you saying to them?

You would just go, like, "Live comedy" as people were walking past over and over and over and over and over, yeah.

But you got on stage, like, as an 18-year-old?

You went on stage.

And how was it?

I mean-- 18 was bad.

I mean, it couldn't have been too good because you didn't do it again for 5 years.

I learned my lesson.

18 was bad, 23 was good.

And then like, once I started in earnest around 32, 33, I knew how to write jokes.

So, it was a matter of figuring out how to perform them.

Is your life going smoothly?

Are you just floating from event to event, feeling good about yourself?

'Cause I'm not.

[Laughter] These are technically the areas of my life that make me feel like something's wrong with me.

[Laughter] So, I get a pit bull named Keith, and everybody told me, "Keith's gonna be your best friend."

And I gotta say, maybe my ninth best friend.

[Laughter] Most interactions I have feel like when you go to throw something away and it's in one of those garbage cans, it's got, like, a garbage hole, a recycling hole, and a compost hole, and you do your best but afterward you're like, "I don't think I did that right."

[Laughter] I've never been married.

I don't think I can guarantee a woman's emotional safety.

Pretty accessible comedy show, huh, folks?

What service does a stand-up comedian offer society?

Ah, the role is a clearinghouse for-- the culture and the world tells us one thing.

And then--and we're all going, like, "This isn't true."

So, as a comedian, you get to go point those things out.

Like, "Hey, here's a thing that "they say is supposed to be this.

"Relationships are supposed to be incredibly harmonious, et cetera, et cetera."

We're sold this narrative and then we get to go and be like, "Actual relationships are like this."

Also, you ever ask married people how it is?

[Laughter] The answers may shock you.

[Laughter] By the way, it's not just men, either.

You ask a woman how marriage is.

Women sound like a politician ducking a hot-button issue.

[Laughter] We'll be like, "Hey, Lisa, how are things with you and Mike?"

And she's like, "Kids are great."

[Laughter] And you ask guys how the marriage is, guys sound like they're reading a hostage letter.

[Laughter] We're like, "Hey, Mike, how are things with you and Lisa?"

And he's like, "Hello."

[Laughter] "I am happy."

[Laughter] "Do not worry about me."

[Laughter] "Worry about yourself..." [Laughter] "and your heathen lifestyle."

[Laughter] "She has taught me so much..." [Laughter] "and made me a better man."

[Laughter] And then she's in the corner like ISIS, like, "Tell him about the duvet cover."

[Laughter] How did it feel switching from being behind the scenes to being Neal Brennan?

Awful.

No.

Mm.

Well, how did it feel being behind the scenes at all?

Like, I mean, was it a party...

I went to NYU Film School, so, I wasn't like-- I was never-- I wasn't working on "Chappelle's Show" going, like, "That should be me.

I should be Rick James."

[Laughs] I--you know, the thing about-- Dave's so talented that it's easy not to compete.

Becoming a performer, there's a--with me, like, being--acknowledging my kind of inner ham is a bit thorny in that, like, the-- my Netflix special just came out and it's really hard for me not to just look at social media and, like, "What else did you think?"

I mean, many people on the show have said, like, you can't believe the bad stuff and you can't believe the good stuff.

Yeah, you can't--no, it's nice to be encouraged, but after a point, it's--you just--it's not human.

It's not like--that level of approval is like, "Ehh."

Well, that brings me to this thing that one comedian said that stand-up is like going on a date, on first dates.

Another guy said it's like driving 150 miles an hour.

Sarah Silverman said it's a [beep]-up need for approval from strangers.

Yeah.

What is it for you?

Like, acceptance?

Is it validation of your worldview?

Is it sublimating the audience?

Yeah, it's validation.

It is satisfying a angry mob.

I will say the thing I like about stand-up and comedy in general is, like, it's pretty fair.

Meaning you can't get fake laughs more than a few times.

Like, they'll--"Ha ha ha."

But, like, you're trying to inspire an involuntary reaction from people.

Yeah.

And over and over and over and over and over.

So, it has to be structurally good, you know?

If you're under 25, you probably are in school or just got out of school.

Student loan debt is [beep] awful.

How many people have student loan debt by round of applause?

[Cheering and applause] That's so many people.

Yeah, I was lucky enough to have dropped out [Laughter] 'cause I realized early on that these student loans are basically small business loans and the business is you.

And you're maybe not such a great business.

[Laughter] Look, if they call them small business loans, no 18-year-old kid would ever get the loan because it's a bad idea for a business.

If you had to go to the bank, to the small business desk and ask, be like, "Yeah, I'm gonna need $150,000," they'd be like, "All right, what's your business idea?"

"All right, here's the idea.

For the next 4 years, I'm gonna get blackout drunk."

[Laughter] "But also, I'm gonna get a degree in sociology."

[Laughter and applause] But you're doing such an interesting thing because you're bringing your depression into it.

So, you have had severe depression for sort of a long time.

Yeah.

And you've tried tons of stuff.

I've tried it all.

Probably 4 or 5 medications.

EMDR.

Pretty helpful.

All kinds of somatic therapies.

Ketamine, transcranial magnetic stimulation, and then, like, a more severe version of transcranial magnetic stimulation.

And then most recently, it's been ayahuasca.

And I did a thing called 5-MeO-DMT, which I cannot recommend.

At all.

At all, to anyone.

Terrifying.

Terrifying for an extended period of time.

And what-- of all those treatments, what has worked the best?

Weirdly, ayahuasca.

I'm sure people don't know what it is.

It's an Amazonian plant medicine.

They make a tea and you drink this tea and you sit in ceremony with a bunch of other dusty White people, and you sit in ceremony and you experience-- you go to--I mean, to me, you go--it's like a god portal.

Which is pretty heavy thing to say, but that's what my experience has been.

Where did you do it?

I've done it in Los Angeles.

It ain't legal.

Uh-huh.

'Cause it's got--the active ingredient is DMT.

So, like, spirit world, and also thoughts you've never had, and you re-experience your own life.

It's pretty wild.

Are you no longer depressed?

It's kind of TBD.

It's TBD.

I'll say that.

'Cause woven into your shows, "3 Mics" and "Blocks," is this very true, very significant thing about you.

Yeah.

And I wonder what would be different about your next special?

I would think that I'll always make specials that are personal.

It's about what facet.

Like, "Blocks" is about inner monologue.

It's about, like, my relationship with myself.

And I guess it's not even monologue.

It's actions.

It's, like, being reckless and shocking myself and being sort of auto-sadism, basically.

Yeah.

Self-flagellation.

So, the depression's part of that.

But I think that's--they make the shows interesting.

So, if I--but I don't think it's because I'm so dark and it's like--it's-- I'm expressing a bigger portion of my experience beyond just, like, the jokes and the, like, "Yeah, and then-- and then he comes in and he goes," you know, like.

And what's come back to you?

Because, I mean, I wrote a memoir about having cancer.

I wrote one about losing my dad.

And what comes back to me is people's stories about being ill and people's stories about loss.

Yeah, it's unbelievable.

It's... it's obviously really touching because a part of you feels-- there's something kind of corny about doing-- talking personally, especially as, like, a male comedian, like, about feelings.

But the response is always overwhelming.

And, like, hundreds of people DM'd me.

Like, the last couple of days, it's been hundreds.

And it's really sweet and touching and-- And are they kind of matching your vulnerability?

No one can match my vulnerability.

Yeah.

No.

Yeah, yeah, they-- of course they do.

Yeah, they really do.

A lot of people relate to it.

Yeah, of course.

And your father was an alcoholic.

Yes.

And when you unpack your life as you do, do, like, all roads lead back to that?

A lot of them.

Yeah.

What kind of alcoholic was he?

Like, an all-day drinker or-- No, he was like--he would-- his--he would come home and have, like, somewhere between two and 4 drinks to allow himself to be like James Cagney.

James Cagney was, like, his icon.

Which is always a weird one, right?

And so, he wanted to be, like, a bully.

Oh.

He would drink to allow himself to be a bully.

Uh-huh.

And he--and it worked.

He was a bully.

Uh-huh.

And where does it sit with you now?

Like, have you processed it?

Do you have a way of thinking about it that, like, keeps it-- keeps you from ruminating, or does it-- I don't ruminate about him at all.

It's a weird thing where I don't--I-- after "3 Mics," it's this weird thing where it was like-- it cleared.

I still have a lot of bad emotional habits from growing up in difficulty.

I think that "Blocks" is entirely a result of that.

Those kinds of emotional habits.

So, "3 Mics" is amazing, and if you haven't seen it, I can't recommend it highly enough, but it's this very clever setup where you have a mic for one-liners, you have a mic for stand-up, which you just read off cards, and then you have a mic for confessional stuff.

Yeah.

I wondered when I watch somebody like Jerrod Carmichael or Bo Burnham, if you think is this a moment or is this the beginning of some new way for comedians to crack open people's thinking?

Stand-up in a lot of ways can just seem like a glib press conference with no questions, you know?

And so, we're all trying to just make it more than that, you know, just make it more than like "And here's another thing.

Yeah, yeah.

Work this out as well.

Yeah."

Well, yeah, it's not even-- it can be, like, more evolved than "Take my wife," but it's-- the tone is so...basic that trying to make it a bit more complicated.

Mike Birbiglia and Hasan Minhaj and Hannah Gadsby and I'm sure I'm forgetting other people.

But yeah, just making it more than a glib press conference, I think, is all of our goals.

And is it in service of the audience or in service of the stand-up?

Well, I would argue it's in service of trying to--as creative people, just trying to do something that's original.

Uh-huh.

Because whenever comedians compliment me on, like, "Oh, it's so cool what you're doing," I'm like, "You can do it."

It's just you have to decide that you want to do it, but it's not-- I guess everybody can't do it, but I can't think of a comedian who couldn't be doing more on stage with the form or the--some--anything.

Anything.

Yeah.

Because there's-- there's just so much more meat on the bone.

Like, Bo's last special was in his outhouse and Jerrod's was at the Blue Note and, like, if you change-- you can change venue and you can change form, I think.

Right, right.

So, we have a thing at "Tell Me More" called "Plus One" where we invite each person-- that's the face you made when you did the duvet joke, I know.

which I loved and I laughed so hard.

I can--you want to go to the next level?

[Laughs] We have a thing at "Plus One"-- Plus One?

[Laughs] What is it?

It's where you shout out somebody that's been really invaluable to your thinking or your work or your well-being.

A guy named Patrice O'Neal, who was a comic.

He died in 2011 or 2012.

Really, really funny.

Really disagreeable.

Mm-hmm.

And, like, we talked on the phone one time.

Arguing in 40 seconds.

And then we argued for two hours.

But he also was, like, generous.

Like, called me one time to just say, like, "Hey, man, you're really funny."

Like, pain in the ass but amazingly funny.

Uh-huh.

Like, amazingly funny.

Great.

Well, here's to him.

Yeah.

We talked to Constance Wu and we asked her 3 adjectives for who people think you are and 3 adjectives for who you actually are.

Good que--good format.

I know.

It kind of worked.

So?

3 things that people think I am.

Cold.

Really?

Yeah.

Yeah.

I think you're very warm.

I know.

[Beep] Back that camera up.

You're gonna burn the lens with my warmth.

I'm gonna singe the lens.

[Laughs] People think I'm cold.

People think I'm cocky.

Uh-huh.

And shut down emotionally.

Wow!

Yeah.

That, again-- That does not square with my opinion.

I happen to agree with you, but you've also-- you're predisposed to like me, so, I just see my life as small and, like, trying to be emotionally in touch and pursuing all these therapies to be more emotionally connected and I-- the cocky thing, it's like-- I think it's a combination of being the youngest of 10 and having a sort of withholding father that I'm always advocating for myself like, "You know, I---uhh, uhh."

You don't"--like, part of me that's constantly like, "You know I did that.

Uhh."

Like, I--self-promo, which is not cool.

Like, it's not what they call a good look.

What do you imagine would happen to your well-being if you didn't have the outlet you have?

If I didn't have the outlet?

I think I'd be, like, a very angry, frustrated... sanitation worker or something.

Like, I think I'd be really mad all the time.

Mm-hmm.

I'm glad you have the outlet.

Furious trash being tossed.

I need more tea.

Come on.

Yeah.

You're almost finished.

Are you ready?

Yeah.

Do a little speed round?

Yeah.

First concert.

George Michael on the "Faith" tour.

Go ahead.

And he was looking-- he was, like, super young.

It was excellent.

Best live performance you've ever seen.

I mean, of anything?

Anything.

It would--I mean, this is an odd thing to say, but it was Dave Chappelle as Rick James when we were shooting the sketch 'cause it was just so--I was technically directing it.

I mean, I was directing it, but it was amazing.

Yeah.

What was your first job?

I was a caddy.

Uh-huh.

Where?

St. Davids Golf Club in Wayne, Pennsylvania.

Hometown.

If your high school did superlatives, what would you have been most likely to become?

I think--I--funny.

Comedian, maybe.

Something.

Do you have a celebrity crush?

Lynda Carter as Wonder Woman will still never-- I'll never fully recover.

Yeah.

What do you wish you had more time to do?

Read.

What's your go-to mantra for hard times?

[Beep] [Laughs] Is there anyone you would like to apologize to?

Nope.

But I've got 75 people that I'd like to apologize to me.

[Laughter] Last book that blew you away.

Somebody sent me, like, a bunch of George Orwell essays.

Uh-huh.

That was excellent.

That's interesting.

If you could pass one law or overturn one Supreme Court case.

It wouldn't be Dobbs.

[Laughs] I'll tell you what it wouldn't be.

No, that'd be a big one.

Yeah.

Roe v. Wade/Dobbs.

Uh...I don't know.

More health care.

More--you know.

If you could say 4 words to anyone, who would you address and what would you say?

That's super odd.

How many words is that?

That's too broad.

That's too broad, Kelly.

Say it.

[Laughs] There you go.

That's too-- yeah?

Right?

Ah, yeah.

That was good.

That was really good.

"That's too broad, Kelly."

That--I think that won.

Correct.

Great.

Yeah.

Congrats.

If you liked this episode, you'll love our conversations with Judd Apatow and Lilly Singh.

You can find them on pbs.org/kelly.

If you'd rather listen to this conversation, check out my podcast-- "Kelly Corrigan Wonders."

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