Judd: Was there ever a moment when you realized, Oh shit, people are actually paying attention to my point of view a lot more closely than I thought they would be?
Jon: There were two moments where that occurred, in some measure. One was winning an Emmy. That got in my head a little bit, feeling like I suddenly had a responsibility, that we had to live up to this thing even if I couldn’t fully define what that thing was.
Judd: Sometimes I liken it to Chappelle in the sense that, for some reason, the responsibility of the show took him away from the idea of having fun, and enjoying himself.
Jon: The sense I got from Dave was it wasn’t so much the responsibility as he wasn’t sure if the show was being received in the way it was intended. I think Dave felt a responsibility, as a black performer, to live up to a responsibility and to not give people—you know, it’s sort of what we call the bucket-of-blood laugh. George Carlin and I used to talk about that a little bit because he would do those shows where he’d be like, “You know, we only bomb brown people. We only bomb brown people except when we bombed Germany they were white people and that’s because they were going, you know, because they were bombing people and that’s our fucking job. That’s our fucking job.” It’s a great bit but you definitely felt, in the audience, that there were some people going, “Yeah, that’s our fucking job!” And for George, it created this sense of “Oh they’re not taking this in the way that I intended it.” And in some ways you have to let that go because it’s something you can’t control. You can only control the intention of the execution, but I think for Dave it became more complicated than that.
Judd: I get it, too, because every time I do stand-up, I wake up the next morning and I feel this shame that is so intense, like I was drunk all night and I don’t remember what I did.
Jon: Really?
Judd: I feel embarrassed at even having had an opinion or a thought.
Jon: But isn’t that the whole—I mean, there’s a certain arrogance in us entering this business. There’s an arrogance in the idea of saying, Where’s that spotlight shining? Oh, it’s up on the stage? Well shit, why don’t I walk up there? What’s in here that’s going to amplify my voice? Is that a microphone? All right, so I got a light shining on me, and my voice is amplified and you’re all looking at me. Well, let me stand here and give you something worthwhile for ten minutes. But I don’t think it goes much further than that, if that makes sense. After that, it becomes a question of, does it resonate?
Judd: What effect does raising your kids have on the mechanics of getting all your work done and presenting your point of view with the world? How old are your kids now?
Jon: Ten and eight.
Judd: I have one about to turn seventeen and one about to turn twelve.
Jon: Oh dear, do they still like you?
Judd: They have to act like they like me because they still need me for some driving. But we’re right at the end of that.
Jon: A little gas money might still keep you in the loop.
Judd: Maybe. But in some way, you must have perfected some sense of balance between your time at home and your time at work—which seems impossible, given how demanding your show is.
Jon: I have done my best, but it’s still not satisfactory, especially as the kids get older. It’s different when they begin to share and experience things that are more complex. It’s one thing to, you know—I have this letter up in my office. It’s something my daughter Maggie wrote to me. It says, and this was after we were down the Jersey Shore, bodysurfing. I think I tanked it and smashed into the sand. It says, “Daddy, I know you are a good writer. You’re a good surfer, too. When you got on that big wave, you got hurt bad. I know you saw a lot of nature. You’re a great dad. Love, Maggie.” That is, like, beautiful. It’s simple. But now, they’re older and they are beginning to articulate things in a much more complex way, and you need to be there more. And nine-to-nine is a shitty schedule for that kind of thing. So I’d like to say that I’ve achieved that balance, but the truth is, I probably haven’t.
Judd: The conversation I get into in our house is: “Dad, we have money, so why don’t you stop working so much?”
Jon: Because I’m an obsessive weirdo?
Judd: And what if Ebola happens in a much larger way and we really need to get the compound solidified?
Jon: Exactly. You are just preparing. I also think, to some extent, you are where you came from. No matter where you end up, no matter what you achieve, on some level, you feel like you belong in a basement underneath a Middle Eastern restaurant telling jokes. That’s never out of you. Leno used to have this. He’d always say, “I never spend any of my stand-up money.” He’d been doing The Tonight Show for like twenty years, and he’d say, “I don’t spend my stand-up money. That goes right to the bank because you don’t want to mess with that. You never know what’s going to happen.” And you’re like, “Yeah, I guess the collapse of Western society maybe, but I think you’re in pretty good shape.” It’s a psychosis more than anything else.
Judd: I know that when I started doing stand-up again, and I would get eighty dollars for my Saturday night spot at the Comedy Cellar, I held on to that money with a joy that I don’t get when the Drillbit Taylor residuals come in.
Jon: Because we’re psychotic and, at some level, not living with a real sense of things. But also, you know, I like working, man. I just wish I was better at it. One of the nice things about doing this show versus stand-up is that there is a moment of Zen at the end of it. There’s a good night. You’re done. With stand-up, you’re never done. You always feel like you’ve got to keep that notebook by the bed. And so you stop experiencing anything. You just exist purely as an observer, constantly trying to figure out if I’m going to be able to work a bit out of this. It’s a different way of approaching life. It’s exhausting.
Judd: How is it that your family’s not angry at you?
Jon: You’ll have to talk to them. I think there’s a certain normalcy. My kids have never known me not to have this schedule.
Judd: Do you enjoy work in the same way after all these years? Has the pleasure of it changed? Because what I find most shocking, as someone who burns out—I mean, we did thirteen episodes of The Ben Stiller Show and I literally prayed for cancellation in my room at night—I can’t believe how vital and alive your show is, and with no sense of burnout.
Jon: It’s hard. In some ways, I think it’s cyclical. I liken it to batters in a slump. Sometimes you just have to simplify, return to basics. You know, All right, well, I’m not hitting right now. That’s when I feel the worst, when I feel like I can’t—the inspiration’s just not there or you feel like you can’t solve the problem with the joke. You can’t elevate. That’s when you feel the shittiest and so, in those moments, you just have to think like a baseball player: Okay, if I’m not hitting, at the very least I’m going to run out every ground ball as hard as I can. Or I’m going to do the best I can in the field. I’m going to try and make up for my lack of creativity until, hopefully, I hustle my way out of that slump. But I will say this: Through it all, I have always retained the ability to feel the joy of the funny. When somebody comes up with something really funny or we hit a jag where it’s clicking, that still feels like that wave you’ve been chasing. It can still make me jump up and down like a little kid. That’s what you chase.