Sarah Silverman and the Stupid, Shitty Things You’ve Done

Lemonada.

Well, I met Sarah Silverman. Man, when was it? Probably 1995, 6, 7, right. when I met Gary Shandling. I did the Gary Shandling show and he graciously invited me to play basketball at his court.

Gary's basketball game was like comedian fight club.

because everybody wanted to be invited to it, but there was no way of knowing when you'd be invited or if you'd be invited. Anyway, so I'm playing in that game and there was only one woman who would play in the game and it was this comedian, Sarah Silverman. She was very quiet and a good ballplayer and sweet. What I remember mostly, I mean, not from that game, but I don't know how much longer after he died this was. It was a couple of months.

It might have been more, it might have been less, but we all decided the extended family that Gary had made, comedians and actors, we all decided we were going to go just have a memorial game, just go play on his court. Nobody had bought his house. It was still just sitting there.

We're all telling Gary's stories to one another.

The weird thing about Gary is that we still do that. Gary had this profound effect on people where he was just memorable.

To be in Gary's house, it sounds a little weird, but to be in Gary's house and on that court where everybody, that was a Sunday afternoon activity where you think life is going to go on forever, and what happened at the game was private.

Here I am talking about it.

I'm David Duchovny, and this is Fail Better, a show where failure, not success, shapes who we are.

Sarah Silverman is an award-winning comedian. She's also a spot up three from the corner, pretty reliable. The Knicks could use her. I think we share something which is an interest in doing many different kinds of expressions through following our need to express our talent, whatever, that is, through different modes of expression. She's done stand-up comedy, musical sketches, scripted TV shows, political campaigns, dramatic movie roles.

Years ago, we actually acted together in a movie, Evolution, a movie directed by Ivan Reitman.

I love this interview because I really got to know her better than I have during this discussion. That was a real gift for me. Here comes Sarah Silverman.

You should know that you're in my top four of stand-ups of all time. Hey.

Top four, definitely. You're my favorite wing player from the Gary Shanling basketball game.

And I wonder, well, first of all, I wonder what that art form gives you that stand-up doesn't or does. What's the connection between the two?

But, you know, listen, when you see a special I've done, I've done that hour for months on the road.

I remember having segues when I first started, and it's so silly, because you're, well, speaking of that, this connects, you know, when really the brain just goes from thought to thought, to thought, naturally, and you can just embody that. And so there's very much an element of acting, because you want it to feel in the moment, and you want it to feel real, and that these notions are kind of coming to you in the moment. And the more prepared you are with that, the more you can be a little loose within the parameters of all that. But it is acting. But then I learned lessons, like I did this Sarah Pauling movie.

You know, Sarah, can you be loud? I'm sure Michelle was. Can you be louder? because you're, like, on a bus? And it's, oh, yeah, yeah, yeah, sure.

And then I go and I'm, like, talking like this still, because in my mind, that's what real acting is. That I equated real acting with just being, like, with that mumblecore, kind of, like, talking very low. It was, like, such a broad lesson to learn, like such a silly lesson to have to learn, but it was, you know.

I went to the David Duchovny School of Acting. No, your acting is totally.

But there's always that thing that exists in your head, or that perfect movie, or that perfect performance, or maybe a perfect joke for you, or whatever, that it's all just partial. that's coming out. And that's why I'm driven to kind of keep, like you, keep evolving. For me it's always, okay, that's going to fail. Like, I know, because that's the way it goes.

I mean, maybe the joke gets a laugh. Maybe, maybe the movie's a hit. Maybe whatever. But I know, every time I go out there, every time I do something that it's like, how am I going to fuck it up this time? You know?

Maybe it needs some small word. Maybe I need to explain more or explain less, you know, or less of a setup. The punchline can't handle that, much of a setup. Or, you know, the opposite. But bombing is failure.

But it also is, you know, in that failure at its best is incredibly informative. Like, you, just don't know what works until you fail. Like, you know, you're sculpting something and every failure gets you closer, ideally. But there are jokes that I try for way too long because I just completely believe in them, but they don't work.

I wrote to myself, more here? Yeah, maybe flesh that out a little bit.

you're not thinking in the moment, you're not thinking, oh, this is really instructive. This is great.

And then you're psyching yourself out. Oh, they hate this. They hate me. I'm not funny. What am I doing?

And then you act like you don't care.

you know, Gary was so good at this. Just be in the moment. Or he struggled with it. And that's why he got good at it. You know, he needed it.

And Rickles said, did you feel funny? And I wonder if you go through that as well. Just like that innate sense of like, well, I'm going to persevere through this. Because I feel funny. I feel funny here.

It worked. Those are mediums that work live. And those like organic moments of connection are so exciting. And especially for me, because I'm pretty good with the crowd. I'm good with the crowd.

If they, you know, whatever, yell out or this or that, but I'm not like Todd Berry or Tig Notaro or, you know, who, like they, could do their whole set just doing crowd work. I mean, it's so masterful and they're so, they trust themselves so completely in the moment. It's like, I'm in awe of it.

child, you know, I thought of that word shock, you know, and that you, you liked shocking people, and that was funny. And I thought of a little depressed girl, and it's like, you're trying to give yourself shock therapy in a way.

And you get addicted to that, that kind of approval.

You know, I, I don't know what kind of depression you had as a kid, whether it was the kind that would keep you in bed, or, you know, or, or you were functional.

And it was, you know, it was. probably, there was so much that wasn't understood about depression and stuff.

I don't have it.

This is going to happen. We tell ourselves horror stories. And the only option that's healthy is to live in the moment. And then that's just something we have to practice, because nobody, very few people, have that down. But you know, so many times I'll be like, Oh God, I've got this and this and this tomorrow.

And I don't, you know, and then I'm like, wait a minute. Am I, am I okay right now? Yeah. I'm on the couch with my favorite person and my dogs. Yeah, I'm fine.

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There are certain failures that don't get wrapped up, that don't get put away completely. They kind of resonate.

And those are the tricky ones that live within you. My mom died about a year and a half ago. I'm sorry. Well, she was 93..

But I could afford to take care of her, but I didn't have the fortitude to physically take care of her. Or to spend the amount of time, when you think back of the amount of time that your parent gives you. I didn't give back a fraction of that time. Instead, I paid for other people to do it. And this is, for me, a failure that lives within me that I can't square, in a way.

When I was reading about how you cared for your dad and your stepmom, I thought that was such a healing thing for you to do for yourself, as you were doing it for them.

The doctor had called me and said, He needs to be in the hospital. And I said, We promised him no more hospital. And the doctor said, You know what? I think that's great. And he's going to die a painless death.

He's going to die from kidney failure, which happens to be a painless death. So I walk into my dad's room and I go, Dad, great news! Which was relative.

But I was able to tell him, You're going to die, and it's going to be painless. And he was so happy. We all just got into bed with him, and the last days were pretty great.

It's not modesty.

And I didn't have this with Gary, and if you don't mind talking about that a little bit. Of course. I did, the week or ten days before he died, I was emailing with him, and he was going to come. We were going to take a walk. And, as with Gary, the day, it got to be two or three and I hadn't heard from him.

And I made other plans or whatever, and he emailed at like three and said, I guess the day got away, so let's do it. You know, I mean, it's classic. Let's do it in a couple weeks. And in a couple weeks he was dead. I know that Gary was, he was a lot sometimes, you know?

Yeah. And to be with him was,

it was always worthwhile, but sometimes I just would feel like I needed to rest or whatever. I just couldn't.

And I couldn't escape feeling, you know, that I had failed him in a way. I mean, not just in that day, but kind of as a friend that didn't know. Because, you know, I mean, as you know, like when Gary had a job, it was all about that, you know, he'd talk to you about the jokes or whatever. Yeah. If he was hosting the Emmys, it would be like six months of like super obsession with that job.

And I would selfishly sometimes kind of pull back because I was like, I didn't want to talk about the Emmy jokes or whatever, you know? And I wonder, I wonder, what was it like for you at that point when he died and even before?

I was kind of having a hard time getting him a little bit. And before he died, he was in the hospital for three weeks and I had no idea. Like whenever he was just gone, I assumed he was in Maui because that was like his, he'd go there and just like meditate for a month or something. So I didn't check in. And then, when I found out he had been in the hospital that whole time, I had like a real panic and I called him upset and angry at him, you know, which is silly, you know, but I was just like, you know, how did I not know about this?

Like, who's your emergency contact? And he said, Bruce. And that made me feel better, like that. he has one, you know. Right.

And, but I was, you know, it's ego, I think more, but it came from just caring about him. But I was so upset that that could even happen. And I not know, not just me, but any of us, you know. And he was very private in that way, you know. Yes.

With his health. He was very private. So, like Bruce Grayson, who's, you know, a very good friend. Maybe one of his best friends was his makeup artist and also played basketball with us, and a friend to all of us. And, you know, kind of kept that secret for him, you know, under his own instruction, I'm sure.

But, you know, God, when I found out he died, I just, I, you know, thinking about that he was alone is just very upsetting to me.

And I think where you want to spend the time is like on the court, you know, remembering that. You know, remembering Gary before almost every game, saying, my head is in.

So word comes back, Gary loves you. Yeah, you're going to do the show.

Does not know? I walk upon the earth. So then we go do a scene and I do meet him. And we do a scene in the hallway and my character gets bumped. And I'm an asshole actor.

You know, I don't like to be bumped or whatever. And I'm misbehaving. And we do one take and then they call cut. And Gary looks at me and he says, how old are you? And I said, 32..

And he goes, what took you so long?

to me. It was kind of a great put down. It was just the best way to welcome me into the whole thing. I'll never, ever forget that. And then how did you guys meet?

I'm like this, and I'm like this. Like, no, just be.

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And we're pretty much inseparable and have more or less zero boundaries. Hence why we named our podcast Pants, because at this point you can't have one leg without the other. And each week we catch up with each other on the big and small things going on in our lives, which then leads to much oversharing and little left to the imagination, whether it's sex or therapy or money fears. Literally nothing is off the table in terms of discussion topics. Oh, and we also like to talk about that wild ride that was The L Word.

You know, the genesis of our friendship. And Pants is out now, wherever you get your podcasts from Lemonada Media.

And so having Trump, when, not that it carried that through all the way up until Trump was elected, but especially when Trump was elected, and what, how the world changed in that way, that character was no longer really amusing to me, because he embodies that completely.

And that hopefully changes over time, because it means you're, you've grown, or you've changed, or the world has changed and you've changed with it, or the world has changed and you haven't changed with it, or all those different variables, you know, in some ways, the stuff I did doesn't hold up, because it's, it comes from a white privilege that, you know, where, you know, listen, I watched that greatest night in pop, you know, they, the, it was just so great that we are the world documentary and they show Prince winning that year, 1984, an AMA award for best black artist.

And I was stunned, and mostly because stunned that that was an award and stunned that I'm sure I watched it and thought nothing of it. And if anything thought it was, you know, I wouldn't have the word for it, like inclusive. And of course that's absurd. And it just goes to show that, you know, as much as we think we have progressed and as woke as we are in this current moment, they were going to look back on it and go like, Oh my God, we had best actress and best actor award or whatever. Like, we'll see things that in a whole new way that we didn't see right now.

And even though it's embarrassing looking back, the only thing really to be embarrassed about is if we don't change from it. Yeah. I, I try to, I accept myself and all the shitty, stupid things I did up until now.

It's really simple and easy.

I've certainly done a lot of apologizing in my life, but how am I forgiving? Yeah. How do you work on that? How do you work on forgiving?

sincere apologies, probably have a hard time accepting themselves.

My laptop is going to die. I have low battery. How much battery do I have left? Does it tell you if you click on it? Oh, well, we'll just go.

If I suddenly hang up, it's because I,

but can I say one thing, even if this is off the air, but your struggle with how you feel about your parents at the end or failing them, you can maybe help yourself by thinking about how, with your kids, you know that they could never fail you. And that's how your parents probably felt. Certainly your mother. I mean, not your father, but I mean, you know, that's so true.

look at you. Thank you.

All right. I love you. I love you too, Sarah. And thank you for doing this.

but what am I trying to get better at in these interviews? What am I trying to get? Am I trying to get an answer as to how to fail better? Because if anybody knew that, they would have told us, you know what I mean? If anybody could turn water into wine, they would have told us, they would have done it.

So it's kind of a, it's a concept that I have, that many of us have, that failure can be instructive and failure can be beautiful.

But how, how do we do that alchemy? How do we go through the process of turning that lead into gold, you know?

And obviously I don't know, or I just tell you.

And my guests don't know, or they would have told you. They would have patented it. You know, that's, that's kind of the lie of the podcast. It's like, oh, you're going to learn. No, I don't think we can learn except by experience, but we can have a glimmer.

Because we're never going to get the answer. All right. Signing off.

There's more. Fail Better. with Lemonada Premium. Subscribers get exclusive access to bonus content, like more of my behind-the-scenes thoughts on this episode. Subscribe now on Apple Podcasts.

Fail Better is a production of Lemonada Media in coordination with King Baby. It is produced by Keegan Zemma, Aria Bracci, and Donny Matias. Our engineer is Brian Castillo. Our SVP of weekly is Steve Nelson. Our VP of new content is Rachel Neal.

Special thanks to Carl Ackerman, Tom Krupinski, and Kate D. Lewis. The show is executive produced by Stephanie Whittles-Wax, Jessica Cordova-Kramer, and me, David Duchovny. The music is also by me and my band, the lovely Colin Lee, Pat McCusker, Mitch Stewart, Davis, Rowan, and Sebastian Modak. Special thanks to Brad Davidson.

You can find us online at Lemonada Media, and you can find me at David Duchovny. You know what it means when I say at David Duchovny. Follow Fail Better wherever you get your podcasts or listen ad-free on Amazon Music with your Prime membership.

Get ready to dive into some of the funniest podcasts around with Lemonada Media's comedy lineup. You can enjoy Choice Words with Samantha Bee, as she laughs along with guests while they talk about their sometimes questionable life decisions. Or listen in as Sarah Silverman answers unpredictable voicemails from her fans on the Sarah Silverman podcast. And don't miss Threedom, where Scott Ackerman, Paul F. Tompkins, and Lauren Lapkus hang out, tell stories about each other, and see who can make the other two laugh the most.

And the best part? You can listen to all of these podcasts and more from Lemonada Media on Amazon Music.