The comedian and podcast legend is still in love with stand-up and nervous itll break his heart.

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It is a transitory life being a comedian.

He continues to perform improv around town and remains the guest all comedy podcasters aspire to land.

Were you always silly?Oh, always.

I was a real class clown, and I liked making people laugh.

There was a lot of roasting and stuff like that.

I know thats why that is!

So when I could make my friends laugh or make a teacher laugh, that was huge.

Making an adult laugh was ahugedeal.

Id like to discuss how and why that happened.

Youve talked about the benefits for you personally.

… but enough that you feel like you get your moneys worth.Which I stand by.

It is like that!

But it really seemed to impact how you approached stand-up.

I was afraid of,What if I found out terrible things about myself?

What if I find out Im a monster?

What if I have a recovered memory?Its really just the fear of the unknown.

Its the fear of finding out stuff about yourself that is not pleasant or is sad.

Its not like,Oh my God, Im gonna be Hannibal Lecter.

Thats going to be uncomfortable.

And then finding out that it has no bearing on whether Im funny or not.

Im not gonna be healed, Im not gonna be all fixed.

So a joke that we have is, All done!

Yeah, it worked!

You figured it out!

You have the answers!Finally cracked it!

Now Im at a point where I could probably stand to go back to talk therapy again.

The only reason I stopped was I felt like I kind of hit a wall.

I was talking about the same things over and over again, and I wasnt able to move forward.

The next breakthrough was podcasting.

You said, I dont want to be onSNL, I want to be the host ofSNL.

And you sort of have done that.

I guess it means a lot to me because I give a shot to be a good guest.

What does that mean to you?I think it means youre not above whatever show youre doing.

You engage with the premise of it in good faith and with enthusiasm otherwise, dont say yes.

The only time I regretted doing that wasTheAdam Carolla Showbecause I was not a listener to that show.

In retrospect, yeah, Im sure thats true, but I dont enjoy doing things that way.

It was not fun, you know?

It was not fun to sit there and be part of the Wack Pack for an evening.

I dont know, Im not good at having a career, I guess …

But it wasnt fun.

I was listening back to those first few appearances you had onComedy Death-RayandComedy Bang!

Did it feel that way to you?

So hes Adamuel.Sometimes its a real reach, but thats what it is!

Thats what the guy is.

Youve done characters in stand-up forever, but youve now become a prolific character creator through podcasting.

How do you create a character when youre doing podcasts?

You really have moved away from impressions.I started doingBang!

If I make up a person out of whole cloth, then Im not confined to that.

Theres no anchor to the real world; it can just be whatever it wants.

And also knowing that I was going to fail.

It made me mad to have to rely on other people in that way.

It made me mad that I wasnt able to communicate the thing that I wanted to communicate adequately enough.

That was how I learned improv, and it also had a profound impact on my life.

It made me more okay with things not being the way that I wanted them to be.

Its not because I cant have anything the way I wanted.

Its just that this is life.

Your mother died in 2007, and then a few years later your father died.

Nothing can prepare you for it.

Another thing about your parents dying is that your relationship with them does not end.

You turn things over in your mind, and you look at them with fresh eyes every few years.

That is where my desire to become funny came from.

But would I have gotten into comedy had my relationship with my parents been different?

Who knows where it comes from?

Its too simple to say my desire to be approved of made me a comedian.

Thats what it feels like, but maybe I would have done it anyway.

I should do this!

I love the approval!Yeah, this is great!

Its not about angst.

Its not about whatever your demons are.

Its a ball, you know?

Theres nothing like when you hear a laughter of recognition about a heavy thing.

It is so cathartic.

Thats no small thing to me when somebody says that to me, and it is very humbling.

I am hugely grateful to have done that.

You started doing comedy in the 80s a time when you win over an audience, then destroy them.

Your relationship is transactional.100 percent.

Thats what it felt like at the time.

But around 2009, 2010, your stand-up started feeling really open.

I remember seeing you then, when you would do a set of just riffing.

Anyone familiar with your stand-up knows what Im talking about.

It sounds and feels like prepared stand-up, but it is clearly generated on the spot.

I was curious what that felt like in the moment.Theres still an element of scariness to it.

Sometimes Im more prepared than others.

Then I have to sit and think,What has been sticking in my mind?

What is a thing that has happened?

He said, you’re free to talk about whatever you want.

Nobodys going to fault you for it not being a heavy, deep topic.

And I was like, Man, youre absolutely right.

Im the one whos building the box, and so it can be whatever I want it to be.

Did it feel like that at the time?Not really.

I mean, my creativity was very much anchored in my sense of who I was as a person.

Whether Im talking about personal stuff or not, this is personal.

This is me and my expression of art and humor.

I would think,I wish I could be a different comedian, a comedian that people wanted more.

I could be more successful, but I cant.

This is just what I do.

You cannotask for anything more than that.

Anything else that happens is gravy.

Yeah, theres always things that I would wish for more.

Maybe Im wrong, but did you stop doing stand-up for a few years?I did, yeah.

Was it a deliberate decision?

Its hard for stand-ups to be like,Im going to stop doing stand-up.Absolutely.

Walk me through that arc of deciding to do that.Really it was a despair.

My last special, which is calledCrying and Driving, which I recorded in 2015 …

I remember talking to my agent and saying, Man, this deal really sucks.

I dont know if I should take this.

Im sure I probably used the word insulting or something.

Then it came and went.

It aired on Comedy Central; I dont know who watched it.

I was told that for the last one I did, the numbers were pretty good.

There was a feeling of,Wow, people are just not interested.

You made some casting decisions with the guests that I think hurt it.

And I was like, Uh, you saw every step of this process!

Youre not seeing this for the first time as the finished pilot.

You know all the stuff that I did.

It felt really brutal to me.

you’re free to say, It didnt go well.

I can fill in the blanks myself.

But that was a real, real turning point to me.

It just hurt too much.

It was really alarming, like,This isnt how this feels!

This is really weird!

I dont like this.So I just went where the joy was, and coincidentally, where the money was.

I was getting good money for doing an improv podcast, so its still an ongoing process.

I dont know if Ill ever do a special again.

I dont want to waste my own time or anybody elses time.

But I dont know.

That shit is not up to me.

Right now, the feeling thats coming back is the duck-below-the-surface-of-the-water kind of thing.

That kind of adds more than I would have suspected previously.

You have to keep your eyes on your own paper, and that is very hard to do.

The real thing you have to fight against, though, is bitterness because thats the end.

Thats the absolute end.

It feels bad, it looks bad, its terrible.

It shouldnt be anybody.[Laughs.]

I mean, it does help to keep me away from that bitterness.

I rememberBeth Stellings specialGirl Daddythat came out man, to watch somebody who has like …

I had to refrain from texting during the special.

I was like, Watch the whole thing!

And to say, Beth, I love this special so much, congratulations.

I didnt have any hand in her ascension!

You did everything I told you about!But I felt that way, you know?

I did feel that pride.

To see somebody get to that point where its like, You fucking did it!

This is where you have cemented your status as one of the great comedians!

When somebody puts out one of those hours thats unassailable, how can you not be excited by it?

This is who I am.

It was, I think, the best night of my career, I think thats safe to say.

I still think its really funny.

Its like,All the material I just did, that was it!

The conceit of stand-up and everyone buys into it isIm saying this for the first time.

Of course Im not.

But its still really very funny to me, and its really fun to perform.

Oh really?Yeah, and its really fun!

Its really fun and silly, and I love performing it.

I ask because do you know the comedian Rose Matafeo?Yeah.

Rose is so funny.

Her most recent special,Horndog, is so great.

She also opened my eyes to things that could be done like incorporating video and stuff like that.

I love that special so much.

It was so good, and that was my first time seeing her do a long set.

I adore Rose, and her sitcom,Starstruck, is great; shes great onTaskmaster.

I am a huge fan of Roses.

I learned so much about rhythm from Tompkins.

Great stand-up requires an equal balance of strong performance and strong writing.

When you see the perfect alchemy of those, it feels like actual magic.

That is very meaningful to me.

This interview has been edited and condensed.

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