Michael Has Issues: A Sad Sad Conversation with Michael Ian Black

Michael Ian Black is one of those self-loathing comedians you’ve heard so much about. His on-stage persona covers a wide spectrum of comic neurosis, deftly swinging between know-it-all-ism to blistering self-hatred, sometimes within the span of a single joke. He is a veteran of stage, television, and film, having performed or written some of the most memorable comedy of the last 20 years, including Michael and Michael Have Issues, Stella, and The State. And yet to hear him talk, one would think he’s getting booed off the stage every night, as he tours in support of his new comedy album, Very Famous.

But Michael Ian Black is nowhere more self-loathing than in “Sad Sad Conversation”, an ongoing YouTube project, where he and other performers and writers upload homemade videos of themselves talking about the travails of getting by in show business. The other “sadsters” include Josh Malina, Steven Weber, Jane Wiedlin of the Go Go’s, Morgan Murphy, Phil Lamarr, Samm Levine, Steve Agee, Sarah Thyre, Lin-Manuel Miranda, and Jill Morris. The resulting “sadness” is by turns poignant, educational, and of course very funny.

PopMatters talked with Michael Ian Black about everything from his infinite “sadness” to the use of existential obscenity in Very Famous to getting away from his stage persona and into a more honest place with his comedy.

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First off, I have to say I’m a huge fan of ‘Sad Sad Conversation.’

Oh, really? You might be the first person I’ve ever met who is.

I’m kind of obsessed with it actually. I think I’ve watched all of the videos.

I don’t think even I’ve done that.

Did you see that James L. Brooks Tweeted about it the other day?

No, I didn’t. What did he write?

He said something about how it shows that no one should ever date a comedian.

[laughs] I think he’s right.

… so I don’t know if that was the goal or not.

The goal was to further alienate people as much as possible. And I think we’re succeeding.

Even on a career level.

Especially on a career level. And to make ourselves even more unemployable.

But really, I can’t be the only one who enjoys ‘Sad Sad Conversation.’

Honestly, if you look at the views per video, each video only gets like 400-500 views. So it’s a really small amount of people watching it, which is fine. I mean, it’s definitely not for everybody. It’s a pretty specific audience. I think you’d really have to care about, like, what are these people’s personal problems. It’s really just … people bitching about their lives.

But it was something compelling to me, when we started doing it. [It’s about] this middle class actor thing. There is a ton of stuff out there for really successful showbiz people and for really unsuccessful showbiz people. But there’s not a lot of stuff about people who are just getting by … or the frustrations with the creative process. And if there’s anything that I think the ‘Sad Sad Conversation’ is totally about, it’s the creative process.

So hopefully it appeals to people other than just shitty actors and shitty comedians. Hopefully anybody who can engage in any kind of creative pursuit can find something in our conversation. You know, is it totally self-aggrandizing? Of course it is.

I was in a panic when I first started it. I just thought, ‘This is just the worst. This is just the worst thing I’ve ever done,’ in terms of being naked and earnest and really letting myself be exposed in that way. And that’s kind of why I made myself keep doing it. Because whenever something feels that uncomfortable, it’s probably worth doing.

And I think you actually talked about that in one of your sad sad videos. About how you want to move into comedy that is less about this ‘Michael Ian Black character’ and into a style that is more honest.

Yeah. Yeah. Unfortunately, I’m much funnier as the fake me than I am as the real me. I wish it wasn’t the case. I wish the real me was just this hilarious jokester. Uh, but I’m not. I’m kind of stoic.

I think that would be great if you did a ‘Sad Sad’ video on stage … just got up on stage and were just really sad for, like, an hour.

[laughs] I mean, if you paid $25 or whatever to go to the Chuckle Patch in Indianapolis, and you saw that? I think you’d be really fucking pissed off.

Maybe. One of the reasons I like ‘Sad Sad Conversation’ is that a lot of the ‘Sadsters’ didn’t know each other before. And so they’re getting to know each other as the viewers at home are getting to know them, too.

Well, yeah. There’s a couple people on there that I still haven’t met. I have never met Jill Morris, though we’ve communicated online. I’ve never met Lin-Manuel [Miranda]. I think that’s it of the regular contributors. I think I’ve only met Steven Weber once or twice. My relationship with Phil Lamarr is pretty distanced. We see each other once every few years, though I feel like I’ve really gotten to know him now. Jane Wiedlin I think I’ve only met once or twice.

But, yeah. I think I get to know people really well over their Twitter. And so to add this conversational component to it, it makes it much more intimate. I really do feel like I know these people well.

Is your desire to get into a more real type of comedy and away from the “Michael Ian Black character” a result of sad sad conversation?

No, no. I’ve been thinking a lot about this since before sad sad conversation. In fact, I don’t think I would have ever done sad sad if not for being sort of already going through this process, and trying to figure out how to be funny as myself.

And I’m struggling. I mean, I’m really struggling with it. And will continue to. That’s what interests me.

It’s not that interesting to me to continue to do what I’ve already done for however many years. Um, it’s just not that interesting. I get sick of myself. The character of me. It’s like reading the same page over and over again. As I get older, my attention shifts, and my focus changes. So I want to be true to whatever that is…

I think any career pursuit is just figuring out who you are at a given moment. And lots of the time, I don’t have a real answer.

Who are some comics who work in this more honest vein that you really look up to?

Well, there are a lot of them. And they kind of approach it in different ways. One of the guys who really started inspiring me early on is a guy named Mike Birbiglia. He really figured out pretty early on in his career that he wanted to do exactly this, just to figure out a way to be himself on stage. I think he was feeling really frustrated by comedy club acts that he was seeing. And it was all very funny. And it was all very good. But I think he felt sort of stifled and frustrated, and like he wasn’t being as real with people as he could be. And that inspires me. People like Louis C.K., who has been in this territory for a long time …

I’m reluctant to … not reluctant. I want to go down that road, but I want to carve my own avenue. And so that’s what I’m doing, or trying to do. And so far, whatever. I don’t know if I’m succeeding. But I also kind of don’t care.

Is not caring part of the honesty?

Yeah, when I say I don’t care, what I mean is that I’m only doing it because I sort of feel compelled to. And so if I have to lose people along the way, then I have to lose people along the way. And that sucks. But I don’t really think I have a choice. So if I say I don’t care, I’m not being glib and saying, “Fuck you if you don’t get it.” I’m not saying that at all. I’m saying, “I’m sorry if you don’t get it, but I have to at least try.”

I love the cover of Very Famous. I think you’re referencing the cover of Dr. Dre’s album The Chronic there?

Yes. Thanks. I was on Marc Maron’s podcast, and he was relentlessly giving me shit about it. And I was like, “Get off my ass. Why do you have to give me shit about everything?” [laughs] I don’t think I used those words exactly. I think he was just trying to goad me. He’s always trying to get my goat.

You two do seem to have an antagonistic relationship.

We do, but it is also a lot of that is just really that we’re ribbing each other. There’s a lot of respect there. A lot of mutual respect. Actually, I take that back. There’s a lot of respect on my end, and not a lot on his end.

Oh, really. That’s good of him to be up front with you like that.

Well, no. He was denying. [laughs] I was making accusations [of his not respecting me], and he was denying them, though not very convincingly.

It’s good you two understand each other.

I think we do actually.

I would love to be the comic who could get up on stage and just have amazing punch-line after amazing punch-line.

Getting back to Very Famous, you talk in your sad sad videos about how you don’t really have a joke-a-minute style, constantly hitting punch lines. But do you feel like that opens up the format to a lot of different kinds of comedy?

It does. You know, it’s a funny problem for comics. Because we perform in a couple of different environments. Some environments are more welcoming of that style than others. And you want to feel like you’re honoring your audience and meeting their expectations. And at the same time, you want to be doing work that feels right for you. And sometimes that’s a tricky balance. Sometimes it’s real work to do a Saturday 10:30 show at a comedy club, and there’s a bachelor party there, and you’re talking about your existential angst, and they don’t really give a shit. They just want to hear dick jokes.

And I don’t know that I’m capable of giving them all the dick jokes that they want to hear right now. I want to give them some dick jokes. And I’ll talk about titty-fucking all night long. But I want some other stuff in there, too.

Don’t get me wrong. I would love to be the comic who could get up on stage and just have amazing punch-line after amazing punch-line. But I just don’t think I’ll ever be that guy. I’d love to be someone like Demitri Martin, who has 300 jokes and they’re all brilliant. But for me, it’s a continual process of reinvention … OK, now I’m getting pretentious.

No, please! Get pretentious!

[laughs] What I mean to say is that every new joke is a challenge.

What you’re saying is that you want to do comedy about, say, the existential angst of titty-fucking.

[laughs] There is no existential angst of titty-fucking. That’s just an existential obscenity. Then again, I can talk about existentialism while titty-fucking.

Alright. That’s an image. So like you said before, you have a non joke-a-minute style. But again, there’s that big desire to be able to just walk into Nashville on a Friday night and point at a guy and say, “I’m gonna make that guy laugh.”

Oh, yeah. I have a huge desire for that.

But do you think those two ideas are in opposition to each other, or if there are how does that play into your comedy?

No, the dream is to meld those two ideas together. And I think the best comics can do that. The best comics can walk into any room and make anyone laugh, and still be really honest about who they are and what’s going on with them. And I’m not like that. And I wish I was, but I’m not.

I think a lot of people would disagree with you.

No, they wouldn’t. [laughs]

You’ve also been a part of some great comedy troupes, notably The State and Stella. So do you feel like when there are more people on stage that that contributes to being able to doing comedy that pushes the limits more?

No, I don’t think so. I think we as a group — Stella, for example, or when I’m working with just Michael Showalter — we just have a style that is ours and comes out. I don’t think it lends itself to being more absurd just because there are more of us on stage together. And I should say, inasmuch as I’d like to be honest in my stand-up, I’d also like to inject that [absurd] stuff, too.

But no, there are a lot of different kinds of freedoms on-stage with other people that you don’t have by yourself, and vice versa. But like in terms of content … no, I think we can do anything in pairs, or in the case of Stella, as a trio. And I feel like I can do anything by myself.

The largest thing is that sense of trust, where those guys will be there on stage to bail me out, if I capsize in my own comedic sewage water. And I don’t have that when I’m by myself.

And honestly, I’m better when I’m with them. I’m not a natural lone performer. But I think I’m learning, and I’m good at it … I mean, it’s not a natural thing. It’s not a natural skill to get up on stage and make people laugh for an hour. I mean, how stupid is that? I mean, it’s just an absurd notion that you would get up on a stage and it’s your job to parade around, and people would give you money for that. It’s just really stupid.

I’m sensing a theme here.

Well, but I mean there’s always been court jesters. And it’s the job of the court jester to tell the jokes. So you know, it’s a worthwhile pursuit. But it’s also sort of insane, that you would travel around to these different places and judge your own work by how well you can make these strangers laugh — people that you would not cross the street to sneeze on …

But no, I’m genuinely grateful if anyone comes to see me. It’s more than anyone could ever hope for that someone likes you enough that they would come and pay their money to perform … I’m indebted for that. And really, I’m grateful for that.

How about during the creative process, when working by yourself as opposed to with other people. I assume that when you’re writing something like Stella that it’s a very collaborative experience, and less so when you’re writing stand-up. Can you talk about the difference between those different creative processes?

I think writing Stella or Michael and Michael Have Issues … it’s exactly that. The fact that it’s a great collaboration, it makes writing fun. And writing is not always a fun pursuit, when you’re sitting there by yourself … and I don’t want to say it can be lonely, but —

I really just don’t know how to write stand-up. I can’t remember ever writing a joke. And yet when I look back, I see that I’ve written them. And so I don’t really know how to view that. I really just don’t know what’s funny. I don’t know how to write a funny joke. I suppose I’m good at writing jokes on Twitter.

It’s something that I’ve heard of a lot of comedy writers say, that they don’t necessarily know what’s funny. They do it in the moment. They might think of something and write some shit down, and then perform it. And it doesn’t work. And you think, “I thought it was funny at the time, but I guess I was wrong.” [laughs]

And so in the end, the people who are good are those who just keep doing it. And then eventually they have enough stuff that people think is funny, and they have an act. But it’s as much more about perseverance than it is about anything else.

Can you think of a joke that you thought was really, really funny, and then you said it to someone — either in collaboration or on stage — and it just totally died?

Yeah, sure. I tried a joke… [laughs] I tried this joke maybe six or seven different times, where I’m talking about the expression, “Shooting fish in a barrel,” and about how it isn’t at all what you think it is. Really, it’s just such an inefficient way to kill fish. [laughs] If you’ve got fish in a barrel, and you want to kill all the fish at once, you really should shoot the barrel. That’s what is going to be the easiest way to kill all the fish. And so rather than saying, “It’s like shooting fish in a barrel,” the expression should be “It’s like shooting barrels.” [laughs]

That’s really funny.

I think it’s really funny, but it always dies.

Well, maybe it would go over better, if you set it up like, “This is not a funny joke.”

Yeah. Say, “this is not a funny joke.” And then it’s funny.

And really it’s more helpful than anything else. You’re just giving them advice, both about the expression and if someone might have a lot of fish and they need to kill them all at once.

Yes, it’s very helpful. Because seriously, if you’ve got a lot of fish in a barrel … you shouldn’t shoot the fish. You really should shoot the barrel. One shot and you could kill all those fish.

Actually on Mythbusters, they tested that theory about whether it’s easy to shoot fish in a barrel, and they found that it isn’t at all.

Oh, wow. They actually tried that then? They actually put a bunch of fish in a barrel?

I’m not sure actually. I can’t remember. But I know they found that it was actually very, very hard to shoot fish in a barrel.

Oh, well, then I definitely can’t do that bit anymore. They’ve done it.

You started out in sketch comedy, but you’ve talked about how you have a great respect for stand-up. Did you always plan to move into stand-up? Did you have a game plan there?

I always thought that, yeah. It was just something that I wasn’t active in pursuing. I did not want to pay my dues. I did not want to just show up at some shitty comedy club on a Friday and be like the fourth guy in line. So yeah, I didn’t want to pay my dues like that. I wanted it to be where if people bought a ticket, they would actually want to see me. They would show up, and they would know who I was because they’d known me from something else. [The way I went about it] is a bad way to be a stand-up comic, because it’s good to be the fourth guy in line, because it’s actually really helpful for their craft. But I was really against that.

So you think that it’s negatively affected your stand-up material that you didn’t have those years of slogging it out in clubs?

You know, it’s affected me a lot. And not necessarily in a bad way. I’ve had to learn much more quietly …

like the first time I went to Montreal Comedy Festival … and the first time I got out there, I had to do a ten-minute set. And I didn’t really have a ten-minute set. I had an hour set. So I didn’t know how to do ten minutes, and every comic knows how to do ten minutes.

And I was bad. I was bad pretty much every single show that I did. I didn’t know how to be in a line-up like that. And I didn’t have the practice. And so I just kind of sucked. And it was really painful. It was really painful to suck every day for like four, five days at Montreal.

So if I had to do that … I don’t really have that kind of energy. And a lot of people do. They can get out there and do a shuck and jive and make people laugh all the time. But I just can’t.

Why do you think the joke-a-minute style gets on so well with the general public?

I think there’s a certain expectation about what comedy is that it’s … you know, it’s a kind of cycle. The things that people see on TV, if you go on Letterman or something, and you’re a comic, generally you have to have jokes every two seconds. It’s expected that people don’t have the patience to sit there and look at something for too long without turning the channel. There’s that hit, that constant hit, that little flash in your brain … and I have no problem with that at all … I want to make sure the jokes are there. If it’s a five-minute story, or a 25 minute story, I still want the jokes to be there.

My audiences are generally pretty kind and are willing to go with you wherever you need to go. But the danger with someone like me is that it becomes masturbatory. Because I know that people don’t want to see me masturbate on-stage. I’m very happy to masturbate by myself at home.

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