Lemonada. Well, I met Sarah Silverman, man, when was it? Probably 1995, '67, right when I met Gary Shandling. I did the Gary Shandling show, and he graciously invited me to play basketball at his court. And Gary's basketball game was like a comedian fight club because everybody wanted to be invited to it, but there was no way of knowing when you would be invited or if you would be invited. Anyway, so I'm playing in that game, and there was only one woman who would play in the game. It was this comedian, Sarah Silverman. And she was very quiet and a good ball player and sweet. And 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 of 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. And we're all telling Gary's stories to one another.

The weird thing about Gary is we still do that. Gary had this profound effect on people where he's 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 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 Ducoubny, 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 next 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 or our talent, whatever that is, through different modes of expression. And she's done stand-up comedy, musical sketches, scripted TV shows, political campaigns, dramatic movie roles. And years ago, we actually acted together in a movie, Evolution, a movie directed by Ivan Reitman. And I love this interview because I really got to know her better than I have during this discussion, and that was a real gift for me.

Here comes Sarah Sutherland. You should know that you're in my top four of standups of all time.

Hey.

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

I miss him.

Yeah. You played my ex-girlfriend in Evolution. Yeah. I just want to ask you quickly about acting, like your relationship to it, because I I know you're going to pooh-pooh it, but I thought you were great in Maestro. I know you're going to tell me it's not a big role or whatever, but it is a big role.

No, I'm just going to say thank you.

Really? Mm-hmm. Okay, I'll wait.

No, I'm going to say... I mean, it wasn't a big.

Okay, well, here's what I saw. I mean, I believed you in that period, and I thought you were just so wonderful to watch. Then when I was preparing to talk to you today and I watched your old specials, and I see I see you commit to those little sketches that you do. You're an actress. 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?

I love acting. I've always wanted to be an actor, but stand-up just took over my whole world. But I do like the idea of doing odd jobs. That's why I'm never really looking to do something that's all-encompassing for an unending amount of time, because I love being able to do a little bit of everything. And that's really where I'm happiest. But listen, when you see a special I've done, I've done that hour for months on the road.

It's a play. It's a play.

It is. It's I'm a very slow honer, and I work an inch, centimeter by centimeter, so that it can feel in the moment and loose. But it's not. A lot of it is acting. You want to feel You don't have... I remember having segues when I first started, and it's so silly because you're, Well, speaking of that, this connects. When really the brain just goes from thought to thought to thought naturally, and you can just embody that. 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 coming to you in the moment. 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 Pauley movie.

She's terrific.

Oh, she's so brilliant. It was really one of the first real dramatic movies I was in. In my mind, I had to say everything like this, just really real and small and everything. There's a scene where Michelle Williams and I are on a bus, and I'm talking like this. She says, Can you guys be louder? Sarah, can you be louder? I'm sure Michelle was. Can you be louder because you're on a bus? It's, Oh, yeah, sure. And then I go and I'm 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 mumble core talking very low. It was like such a broad lesson to learn, like such a silly lesson to have to learn, but it was.

I really feel like you're insulting me right now.

I went to the David DeCovny School of acting. No, your acting is totally- No.

Let me tell you something. When I was auditioning, auditioning, not getting anything, before I worked at all, I'd always get flat or more energy, like louder or whatever, like what you were experiencing. I'm sure it was because I was tight. Part of it was tight. 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 keep, like you, keep evolving. For me, it's always Okay, that's going to fail. I know because that's the way it goes. I mean, maybe the joke gets a laugh, maybe the movie is 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?

Well, sometimes I'll have a joke that I love so much, and I just can't get it to work. I either ultimately have to go, Well, I'm wrong. This isn't funny, or I have to figure out what it's missing. Maybe it needs a pause. Maybe it needs some small word, maybe I need to explain more or explain less or less of a setup. The punchline can't handle that much of a setup or the opposite. But bombing is failure, but it also is in that failure at its best is incredibly informative. You just don't know what until you fail. 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.

What's an example of that? Shit. Could you think of one? Think of one that's been on the shelf for a while?

Yeah, because I'm in the middle of it all now. I mean...

The yellow pages. I love a legal pad.

Yellow pages, baby. I never heard that called that. That makes sense. What do you got there? I mean, it's really embarrassing. Oh, please. I have a show today. It's just like this just says, Diarrheia Anne Frank. And then I have the gall next to it in parentheses. I wrote to myself, more here? Yeah, maybe flesh that out a little bit.

Maybe a little more. You talk about bombing. So if you're bombing, you're not thinking in the moment, you're not thinking, Oh, this is really instructive. This is great.

I try to because the worst thing as a comic is bailing, bailing on your set, meaning you just... Just like we do in life, you're thinking that you know what the audience is thinking, and then you're psyching yourself out. Oh, They hate this. They hate me. I'm not funny. What am I doing? Then you act like you don't care. I don't care. You bail on your material and everybody loses. It's a real lesson from doing it a long time, I guess, or maybe people learn it earlier, that you have to... Gary was so good at this, just be in the moment, or he struggled with it, and that's when he got good at it. He needed it. Right.

Did Gary ever tell you the Don Rickles' story about when he was in Vegas?

Tell it, no.

He was a younger comic. Gary's a younger comic. In Vegas, and Rickles is in the audience, and Gary's super excited because Rickles is the master. And afterwards, Rickles comes to the dressing room to say hi to him, and Gary's like, Well, was I funny? And Rickles said, Did you feel funny? And I wonder if you go through that as well. Just that innate sense of like, I'm going to persevere through this because I feel funny. I feel funny here.

Yes. Listen, when I feel funny and it feels magical and the audience is like we're as one. It's so exciting and it feels so good, and you should trust it and believe in it. So what I'm about to say, I don't want it to take away from this. But it is interesting I want to say I just started recording myself on stage, probably in the past 10 years. I've been recording myself because it's so hard to do because once you know you're recording, even though you may never listen to it back, or if anyone listens to it back, it's just you. But there's something about when it's recorded, it's like why it's hard to pull off magic or improv on television or on a recorded piece and not live. Those are mediums that work live. Those organic moments of connection are so exciting, especially for me, because I'm good with the crowd. If they whenever yell out or this or that, But I'm not like Todd Berry or Tig Notaro, who they could do their whole set just doing crowd work. I mean, it's so masterful, and they trust themselves so completely in the moment.

It's I'm in awe of it. Right.

I read about you. I didn't know. I mean, we've known each other a long time, but we don't really know each other. We have this connection through our beloved friend, Gary, which is deep, but we've never really exercised our friendship in that way. I'm reading about you to talk to you today, and I was very moved by how you started to tell jokes as a depressed child. I thought of that word shock and that you liked shocking people, and that was funny. I thought of a little depressed girl, and it's like, you're trying to give yourself shock therapy in a way.

That's so interesting. Yeah. I think realizing that origin of being a comic that peddles in shock. It was like my dad was one of those dads that taught me curse words when I was three, and then I'd say them, and I would get this wild approval from adults despite themselves. I made my arms itch with glee. You get addicted to that, that approval.

Do you remember your first joke?

Well, my dad taught me to say, Bitch, bastard, damn shit, and I yelled it in the middle of boys market in Manchester, New Hampshire, and people were horrified, and it felt like love.

You killed.

I killed.

Still a good one. I think you could still hit with that one. I don't know what depression you had as a kid, whether it was the kind that would keep you in bed or you were functional.

I stopped going to school, and I couldn't be around. I went from being the most social kid where all my friends came over after school to not being able to imagine being normal and not just wanting to be in bed and alone. I would see my friends just living life and be like, How do they do that without crumbling? I don't know. It was probably there was so much that wasn't understood about depression and stuff.

Right. How did you conceive of yourself at that moment? I mean, what I'm getting at in a way is when I have felt depression, it feels like failure to me. It feels like I'm failing as a human being. I don't have it. I don't have it.

Yeah. And it's so much of what we live in is depression that's toiling about the past or anxiety, which is the what ifs of the future, even though we've never predicted anything that's ever happened in our lives. But we think we can. We get around and go, What if this? What if that? What if this? What if that? This is going to happen. 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 very few people have that down. But so many times I'll be like, Oh, God, I've got this and this and this tomorrow, and I don't… Then I'm like, Wait a minute. Am I okay right now? Yeah. I'm on the couch with my favorite person and my dogs. Yeah, I'm fine.

But when you're a kid, you don't have access to that rational self-talk.

No.

It's a beautiful adaptation that you're still doing.

Yeah. I guess I'm pretty amazing.

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I'm sorry.

Well, she was 93.

Well, I killed her.

And she had had dementia for quite a while, so it was merciful by the end. 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.

It was. It was really hard with my stepmom because it was a horrible death. She had cancer and she wanted to live. Whereas my dad just wanted to be with her once she died and was totally unafraid of death and thrilled when I I told him that the doctor had called me and said, Your dad is dying. 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, I realized. 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.

And you probably didn't... Did you feel the need to litigate whatever anxieties or misses that you had in the past?

No, but with my mom died eight years earlier and I wasn't as there. I wasn't there.

But the question is, how do we go about forgiving ourselves for that a failure?

How do we forgive our parents? We say they did the best they could with what they were given. That's what you did.

Yeah. If I could extend myself that generosity, it would be a good thing.

Yeah, why not? It's good for everyone, too. The more we, what is it, flagellate or we torture ourselves, the less space we even have for others. So it really isn't a modest existence. It's not modesty.

It's actually selfish. It's all-consuming, isn't it? Yeah. I didn't have this with Gary, and if you don't mind talking about that a little bit. Of course. The week or 10 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 it like three and said, I guess the day got away, so let's do it. I mean, it's classic. Let's do it in a couple of weeks. And in a couple of weeks, he was dead. I know that Gary was a lot sometimes. To be with him, it was always worthwhile, but sometimes I just would feel like I needed to rest or whatever, or I just couldn't And I couldn't escape feeling that I had failed him in a way. I mean, not just in that day, but as a friend that didn't know. Because as you know, when Gary had a job, it was all about that. He'd talk to you about the jokes or whatever.

If he was hosting the Emmys, it would be six months of super obsession with that job. I would selfishly sometimes pull back because I was like, I didn't want to talk about the Emmy jokes or whatever. I wonder what was it like for you at that point when he died and even before?

I mean, similar, really similar, where I just... Basketball was the joy of... Those Sundays were just the joy of my life. But In our relationship, we were close, but sometimes it was hard to have the bandwidth for it all. But he would make time for you, and it is harder to make... I wish I was better at being reciprocal, and in a lot of ways, I'm sure I was. But there were times towards the end where it was hard to decipher his code a little bit. Yeah. He'd say things that I don't know if he was kidding or serious. I was having a hard time getting him a little bit. Before he died, he was in the hospital for three weeks, and I had no idea. Whenever he was just gone, I assumed he was in Maui because that was like his... He'd go there and just meditate for a month or something. I didn't check in. And then when I found out he had been in the hospital that whole time, I had a real panic, and I called him upset and angry at him, which is silly. But I was just like, How did I not know about this?

Who's your emergency contact? And he said, Bruce. And that made me feel better that he has one. But it's ego, I think more. But it came from just caring about him. But I was so upset that that could even happen. I not know, not just me, but any of us. He was very private in that way with his health. He was very private. Bruce Grayson, who's 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 kept that secret for him under his own destruction, I'm sure. But God, when I found out he died, I just… Thinking about that he was alone is just very upsetting to me.

Yeah.

But again, can't really toil that much about it because it's done. It's happened.

Right. I think where you want to spend the time is on the court, remembering that, remembering Gary before almost every game saying, My head is in. Yeah. If the ball hits his head.

My head is in.

Just silly shit like that. It's just I get a warm feeling when I think about it. I remember Neelen doing a draft coach. Have you ever heard of it?

Yeah, eating the leaves. I was just thinking about the other day.

You're the thing of a giraffe coach? Come on, guys. Take a knee. Okay, here we go. We want to get back on D.

Then you start nibbling on the tree leaves.

Because he's the only guy tall enough to actually nibble on the trees.

Is there anyone funnier than Kevin Neelan? There isn't. I mean, even in Gary's Memorial, Marona Mi. I mean, he was sobbing and killing.

I guess that's the perfect standup, right? To sob and kill at the same time. Maybe that's where you're heading, Sarah.

Yeah, right. To bear your whole heart and kill.

Yeah. I'll tell you two things, Gary. I don't know, second, third year, X-Files. I just said, I want to do SNL and I want to do Sanders because I love that show. And I would get the VHS tapes sent up to Vancouver. So word comes back, Gary loves you. Yeah, you're going to do the show.

That's how you met doing Sanders?

Yeah. I go there and I watch him do a talk show segment. I sit in the audience part, and he passes by me 10 times, 15 times, clearly has no fucking clue who I am. It does not love me at all, does not know I walk upon the Earth. Then we go do a scene, and I do meet him, and we do a scene in the hallway, and my character gets bumped. I'm an asshole actor. I don't like 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? I know, right? And I tell you, it melted my heart because I wanted to exist in that world of funny performance, whatever. I was known for the X-Files, which is not really that funny. I just felt my soul was in this place. Here was the king of this world to me. It was a great put down. It was just the best way to welcome me into The whole thing. I'll never, ever forget that.

Then how did you guys meet?

Dave Rath took me to basketball one Sunday. Oh, really? I worshiped him, so it took me a long time to be myself at all there.

I was like- Didn't want to shoot too much.

Didn't want to shoot too much, didn't want to say too much. I was trying to be cool.

How do you try to be cool during the basketball game? How does that go?

Well, I mean, just trying to be cool with him, like make cool, biting comments. It wasn't until I let myself be warm and human that we connected. It was like a real friendship happened.

Yeah. You almost remember that as a moment or that was just a curve?

Vaguely, I remember thinking, I'm trying to act cool, and that's not what he's about. And what if I'm just... So we were playing ping-pong.

Oh, he was a good ping-pong player. People don't know this. Really good.

Yeah. I just asked not after him. When you're trying to impress someone, something that you don't realize is you make it all about yourself. I'm like this, and I'm like this. No, just be. And Take in them.

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It wasn't really a conscious like, Hey, that stuff doesn't work, so I'm going to go a different way. I think I just very naturally started changing in terms of my first comedy special, Jesus's magic is like, I'm Sarah Silverman, but I'm totally doing a character, and that character, and it carried on into my Comedy Central show, The Sarah Silverman program was an arrogant It's ignorant. Having Trump, not that it carried that through all the way up until Trump was elected, but especially when Trump was elected and how the world changed in that way, that character was no longer really confusing to me because he embodies that completely.

Sure. Was that just organic to you on the inside, or did you feel that in relationship to an audience? That shift.

No, it wasn't like, Well, the audience isn't laughing at my racist jokes anymore. It's just like it is art. It's just like a painting on a wall in a museum, if you go and see it every single day, it changes because your life changes, your experiences change, and the world around us completely change. So what you're seeing is going to be inferred with a whole new set of perspective. I learned this pretty early on, that comedy really dies in the second guessing of your audience, that you really have to stay with what is funny to you. That hopefully changes over time because it means 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. In some ways, the stuff I did doesn't hold up because it comes from a white privilege. Listen, I watched that Greatest Night in Pop. It was just so great that We Are the World documentary. They show Prince winning that year, 1984, an AMA Award for Best Black artist. I was stunned, mostly because stunned that that was an award and stunned that I'm sure I watched it and thought nothing of it.

If anything thought it was—I wouldn't have the word for it—inclusive. Of course, that's absurd. It just goes to show that 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 reward or whatever. We'll see things in a whole new way that we didn't see right now.

Yeah, I've thought about that. To be judged by the future as, in my fantasy, it's always as a meateater. I was like, Oh, she was a funny comic, but she was a meateater.

Yeah, but we can't foresee it now. We don't know now what we don't know. That's part of the reason why I think it's important to learn from the past and be changed from the past at a cellular level. But to litigate the past is, to me, a less successful plight because all of us knew just only what we knew up to that point. And even though it's embarrassing looking back, the only thing really to be embarrassed about is if we change from it. I accept myself and all the shitty, stupid things I did up until now.

I've also read that you love apologizing.

It's not like I love apologizing. It's just that I am not afraid to apologize when I'm wrong. If I'm sorry, I apologize always. And if I'm not sorry, I don't apologize. It seems like a really good way to live by. It's really simple and easy.

I think you just have to acknowledge some personal, I can use the word again, failure and an apology. I have failed you. I have failed in some way, and it has to be sincere. But I also think I would rather We're, as a culture, focused on forgiveness as well. How do we do that? Instead of like, okay, maybe I'm an expert apologizer. I've certainly done a lot of apologizing in my life, but how am I at forgiving? How do you work on How do you work on forgiving?

By being able to accept yourself and forgive yourself. I know that sounds corny and textbooky, but there's a reason for that. There's a reason why that sounds trite. But I mean, people who No one accept apologies, 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- I won't tell you personally. 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. Shit, I mean, I'm your father, but I mean...

That's so true. My kids could not fail me. They could not. Yeah. Yeah. Look at you.

Thank you. Mic drop.

I love talking to you. Your battery is dying, so your words are not actually synced up with your mouth.

I noticed that, too.

But your meaning is, and I appreciate it, and I will dwell on it later. Thank you. I appreciate that. All right.

I love you.

I love you, too, Sarah, and thank you for doing this.

It was really fun. Yeah, it was.

All right, here we go. I wanted to talk a little about the Sarah Silverman podcast. But what am I trying to get better 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 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? 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. That's 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 Zema, Aria Bracci, and Donny Matias. Our engineer is Brian Castillo. Our SVP of Weekly is Steve Nelson. Our VP of New Content is Rachel Neill. Special thanks to Carl Ackerman, Tom Krupinski, and Kate D. Lewis. The show is executive-produced by Stephanie Wittleswax, Jessica Cordova-Kramer, and me, David Dekovny. The music is also by me and my band, the lovely Colin Lee, Pat McCusker, Mitch Stuart, Davis Rowland, and Sebastian Modack. Special thanks to Brad Davidson. You can find us online at Lemonada Media, and you can find me at David Ducouveny. You know what it means when I say at David Ducouveny. Follow failbetter wherever you get your podcast or listen ad-free on Amazon Music with your prime membership.