When attempting to describe Michael Ian Black’s wide-ranging career, hyphens are helpful. Black is an actor-comedian-host-screenwriter-director-podcaster-spokesman-etc. And in the last few years, he’s become an author, penning three books for adults and four picture books for children. Pretty impressive for a guy who doesn’t even self-identify as a writer.
“I don’t know how to describe my own occupation,” Black says. “So I try to avoid answering that question as much as I can. I definitely write. I wouldn’t say that’s my primary occupation, although it’s certainly the basis for a lot of what I do.”
However Black chooses to label himself, the word “author” will forevermore be shoehorned into his biography, as he is responsible for both hilarious and poignant collections of prose. His first book, My Custom Van: And 50 Other Mind-Blowing Essays that Will Blow Your Mind All Over Your Face, is a compendium of absurdist essays with titles like “What I Would Be Thinking About If I Were Billy Joel Driving Toward a Holiday Party Where I Knew There Was Going to Be A Piano” — originally published on McSweeney’s Internet Tendency — and “A Series of Letters to a Squirrel,” which is pretty self-explanatory.
Black, a self-professed liberal, then co-wrote America: You Sexy Bitch: A Love Letter to Freedom with Senator John McCain’s daughter, Meghan. The book project, published as alternating journal entries, involved a cross-country road trip, the modestly stated goal being to “change the way politics is discussed in America.” The idea, Black says, was hatched one night on Twitter when he suggested a collaboration to McCain, who, somehow, readily agreed.
In 2012, Black released You’re Not Doing It Right: Tales of Marriage, Sex, Death, and Other Humiliations, which featured his most personal work to date, including reflections on the ongoing challenges of marriage and family. Defying any perceived expectations of ironic detachment or snark, he read a heartbreaking piece about the early loss of his father on This American Life — for a Father’s Day episode — with very few jokes or asides. It was, quite simply, straightforward and sad.
Black is currently at work on a new book in the mode of his memoir, although he isn’t super eager to talk about it, for fear of sabotaging his own efforts and/or momentum. Between raising his kids and participating in non-authorial pursuits, it’ll be another year or more before the book is completed, Black says, adding that he intends to make it into another honest account of his collected life experiences.
Black is also a prolific and hilarious tweeter. While he’s claimed that his (nearly) 2 million Twitter followers are a result of the website promoting him in its early days, his current bio — “Noted expert” — is essentially the truth, at least in the realm of 140 characters or less. Black is a consummate wordsmith, skilled at communicating short, funny thoughts in rapid-fire succession.
It’s hard to put my finger on when I became aware of Michael Ian Black, whether it was his work in MTV’s The State or Comedy Central’s Stella or the cult classic movie Wet Hot American Summer or his numerous VH1 commentaries on shows like I Love the 80s. It kind of seems like he’s always been bouncing around movies and television, ubiquitous in certain comedy circles. As an actor, Black oftentimes will partner up with his longtime friends/collaborators David Wain and Michael Showalter, but with his books, it’s generally a solitary pursuit, working from his home office in Connecticut.
We recently spoke by phone for an hour — and then reconvened for another quick round of questions via email — covering some of the biggies: writing, comedy, truth, memory, expectations, Twitter, and bad Amazon reviews.
You’ve mentioned that your last book was an attempt to shed the Michael Ian Black persona and get to something that’s truer to who you actually are on a day-to-day level. Did you get to the point where you’re so known for a specific type of comedy that you want to show a truer version of yourself?
Michael Ian Black: It’s more about not feeling boxed in by any one thing and feeling like I have to be a certain way. The extreme of that is somebody like Gilbert Gottfried, who’s only employable as a kind of screaming maniac. And he’s not like that at all. You know, as comedians or actors, you can wrap this persona so tightly around yourself that it can become suffocating and I didn’t want to do that. I was feeling constricted by my own work and felt like I needed to break free of that.
What do your comedian friends think when you write seriously?
MIB: Oh, they don’t read anything that I write. They’re too wrapped up in their own shit.
Wasn’t there talk of publishing your last book under a pseudonym?
MIB: Well, yeah. I didn’t want it to be about me in the sense that I am a public person. And I didn’t want that tied up with it. I wanted it to be more universal than about a specific — for lack of a better word — “celebrity.” This could’ve been anybody’s memoir.
Just letting the book speak for itself without connecting it to the fact that we’ve seen you in stuff before…
MIB: Exactly. I didn’t want the hook to be, “Oh, here’s the guy who was on basic cable once. He wrote a book.” I wanted it to be, “Here’s a well-written book.”
And is that the reason why there was no mention of your comedy career in your last book?
MIB: That was conscious too. It had nothing to do with my career. And it was conscious in the sense that I just don’t give a shit about it and so I had no desire to write about it. I mean, I give a shit about it obviously for me, personally, but it wasn’t anything that I wanted to write about. I didn’t think it was particularly interesting.
I feel like there’s a segment of people who would enjoy reading about that element of your life, though.
MIB: Yeah, but that number is probably more than three and less than seven. You know? I’m not Tina Fey. I’m not somebody who’s had a career worth celebrating. I’m happy with it, in the sense that I’ve been able to have a career at all. But for me to come out with some triumphal memoir about my success in show business would be absurd. And then the flip side of that is that I could write a book about my not-so-triumphal career in show business, which maybe I’ll do at some point, but I don’t have a desire to do it now.
I’ve heard you talk about being in the “middle class” of show business, implying that you’re not at the level of, say, Tina Fey, but you’re also not struggling. Do you feel like — because you’re actually good at a number of different things and you bounce around to so many different projects — that you possibly dilute your chances of reaching those heights? Instead of just focusing on books and becoming the next big memoirist, you’ll write a book and then go appear on a TV show.
MIB: I think about it all the time. And I feel a bit dilettantish about my entire career. But, at the same time, I’m fortunate in that I’ve been able to do a lot of things. And I’m unfortunate in exactly what you described. In being able to do a lot of things, I don’t know that I’ve ever gone as far as I can in any one of those things, for not having focused on any of them, particularly. But I get bored and I get restless. As an actor, you can show up on a set and be on a TV show for three or four years, or whatever it is and, by the end of it, you just want to do something else. So I write a book. And, by the end of the time I’m writing a book, I’m tearing my hair out and I want to go do stand-up. And then I want to do something else. I don’t know why it is true with me that I can’t just be satisfied doing the one thing, but I’m constantly flitting from one thing to another. Part of it is fear and just feeling like you gotta keep all these balls up in the air, because you never know when any one of them is going to come crashing down. And part of it is a short attention span.
I read an interview where you said that you felt like stand-up comedy was the closest you could get to your actual self. Do you feel like your books trump stand-up in that respect, considering everything you’ve revealed?
MIB: I think so, because stand-up still requires a kind of form that the books don’t require. So yeah, I would say the books are closer. But, you know, you can do things on stage just with a look or a gesture that you obviously can’t do with a book, which is also helpful. Both of them come close.
What were your expectations about what your memoir would be? Did you know that it would turn out to be so serious and revealing?
MIB: My expectation for myself, my challenge to myself, was to tell the truth. To just be honest. And let everything kind of go from there. So I didn’t receive any pushback from my editors in terms of its tone. Although I think it’s funny too. I think there’s a lot of humor in that book. In some ways, I think it’s too jokey. There’s passages in it, if I pick it up — which is almost never — that I could see eliminating just because they’re trying for a joke.
Your old reflex of always heading for something funny…
MIB: Yeah. That’s something that I struggle with a lot in terms of writing my new book, which is how much humor to put in it. As I was going, I was finding it was utterly joke-less. And when I did show that to my editor, she was like, “You know this is utterly joke-less.” And I’m like, “Yeah, isn’t it great?” And she said, “No, it’s really not.” And because of the subject matter, it kind of demanded either no jokes or more jokes. So that’s where I’m struggling. It’s a constant struggle with me in terms of, like, what expectations do readers have? And do I give a shit what expectations they have? But the larger question is, for myself creatively: Am I sort of pinching off my own voice if I don’t let myself be funny because obviously I do do that. Am I being untrue to myself? So it’s a constant struggle and balancing act.
Then again, you’ve already proven that you’re funny throughout your comedy career. So is it satisfying to essentially say, “You guys know I’m funny, now I will write some serious stuff?”
MIB: Well, that’s part of what’s going on with me is the desire to prove that I’m a good, serious writer. But then, the other part of me is struggling with that need for validation and going, “Who am I trying to prove this to?” And not really knowing the answer to that question. Am I trying to prove it to the New York Times? Because I don’t think they really care, one way or the other.
Is it liberating or therapeutic to reveal as much as you did?
MIB: I think whatever burden or guilt I felt about things that I wrote about, I probably let go of that a little bit before I started writing. I was much more concerned about just sort of laying it out there than I was about finding catharsis in it. I didn’t feel particularly like I was letting anything go, necessarily, for good or for bad. And I didn’t feel any sense of embarrassment at anything that I expressed in the book. It didn’t feel like therapy, so much.
You write a beautiful scene, set in the days before you became a father, where you cry on the side of the road, while sitting in your car. You’ve said that the chapter is about hope and nostalgia. But was it the process of looking back on this event years later when you realized what was really going on?
MIB: Yeah, I think writing for anybody helps you order your life. It helps you arrange your emotions and your thoughts and it helps to provide perspective. In that sense, it was great to tumble those things over in my mind and contemplate why I held on to those particular memories. And I think writing does help.
Do you clear the personal stuff with anybody?
MIB: Only my wife. That was part of our deal. But I didn’t give her a lot of time.
Was there anything she asked for? An amendment or deletion?
MIB: Well, there was one thing in an early draft, that she insisted I take out, about a previous boyfriend she had. And the only other thing that she really insisted that I change was — I wrote about our honeymoon in Amsterdam and how we ordered crepes at some little restaurant. And I said that I got a crepe with ham and cheese and that she got a crepe with banana Nutella. And she yelled at me and she insisted that I change that. She said, “You are the one who got banana Nutella and I’m the one who got ham and cheese.” She said, “I would never get banana and Nutella because that’s a child’s food.” And I thought, “Well, if that’s the biggest thing that she needs me to change, then I guess I can change that for her.” I think she didn’t want to be perceived as a stupid American.
So, how do you find that balance between telling the truth about your family without hurting them? Or is it all pretty much fair game?
MIB: I definitely didn’t feel like everything was fair game and there’s a lot of things I didn’t say that I could have that may have hurt certain people in my life. I found no reason to do that. And so, consequently, a lot of the jokes and a lot of the idiocy in the book is on me, not on other people. That was a deliberate choice. But, at the same time, I also didn’t want to paint everybody as being better than me. And I don’t think I did. I mean, I wanted to write about my wife’s flaws and my shitty kids and everything else. So I did. And I tried to do it in as sensitive a way as I could and still be honest. So yeah, I was conscious of it and made a conscious choice to not hurt people if I could help it.
I’ve heard you say that a major theme of your last book is that we’re all “colossal fuck-ups.” Is that how you still feel? That we’re all somehow damaged?
MIB: I think that’s true about that book and about how I feel about everybody in general, which is, there’s no such thing as somebody who really has their shit together.
Do you feel like you’re taking it a step further in this next book? Will we see even more of the real Michael Ian Black?
MIB: Ideally, that’s what I would like. As it’s turning out, it’s a step forward in the sense that setting yourself on fire might be a step forward.
So it’s pretty personal, then?
MIB: It’s not even that it’s so personal. It’s that I’m having such a hard time writing it. Tonally, it’s similar to You’re Not Doing It Right. Content-wise … well, it’s not exactly a memoir, but it’s essays about personal things. I can’t talk about it too much because I’m superstitious and, if I talk about it, I feel self-conscious about it and I think the whole thing’s dumb and then I don’t write it anymore and then I go to my grave.
I know that it took you two-and-a-half years to write your last book. Is that about the pace of this current one?
MIB: It seems like it. I mean, when I made the deal to write it, I was like, “Give me a year.” And that year ends about … three weeks ago. And I’m nowhere. It’s going horribly.
Is it? What’s your process like?
MIB: I generally get up in the morning and get my kids ready for school and then, once they’re off, I read the newspaper and then it’s time to write the book. Which largely consists of reading Twitter. That seems to be mostly what writing my book is: reading Twitter.
And after you’ve caught up on Twitter, will you try to bang out a full chapter?
MIB: I wish it were that neat. It’s not. It’s generally write, get stuck, go back, rewrite, try to move it a little bit forward, get stuck, go back, rewrite, try to move it a little bit forward. For two-and-a-half years.
Obviously you’re raising children and you have all kinds of hands in different creative pots. I’d guess your writing-time is actually spread pretty thin.
MIB: Yeah, I mean it’s that, [but] it might just be that every writer has their kind of rhythm. And it might just be that that’s my rhythm. I don’t know. I was hoping to write it faster. I sort of thought, “I know how to do this now.” But it turns out I don’t know how to do this.
When you’re writing, do you have somebody other than your wife or your editor that you’ll show it to? Do you have trusted people who read your work?
MIB: I generally don’t show it to anybody. The fact that I showed [the new manuscript] to my editor at all was more about proving to her that I was actually working on it. Although I did need feedback and she gave me good feedback. But generally, yeah, I don’t show anything to anybody. I mean, I’ll sense when it’s done. I’ll sense when it’s ready to show. And I’m nowhere near that right now.
You’ve implied in interviews that don’t know what you’re doing with your writing, that you have nothing to say, but that you also consider that feeling to be normal. Do you still go through that same crisis-of-confidence every day?
MIB: I think that must be common for writers. I don’t know many writers, so I don’t know. I’ve never really talked to any about it. But I should refine that to say: It’s not that I don’t think I have anything to say, it’s that I don’t know what it is I want to say, or how to say it, or the best way to express myself, or why anybody would care.
With that said, it seems like most of the response to your last book was positive.
MIB: Oh, there’s plenty of bad reviews on Amazon. [Long pause while Black seeks out some reviews of his work online; he then begins to read:] “You, sir, did not do anything noteworthy. The only thing you did was make a catchy book-cover and well-written back page to suck people in. I’m glad you made money on it, though.” That’s one of them.
Oh, man. I’m sorry that you’re seeking these out for my benefit.
MIB: It’s one of my greatest joys. Here’s another: “This book was horrible trash. It was a real chore to finish reading this book because Michael Ian Black is such a big pussy and completely pussy-whipped by his bat-shit crazy wife.” And then it goes on from there. “Not funny or insightful. Not what I expected. Disappointed.” “You’re Not Doing It Right: Boring.” Plenty of bad reviews.
I guess what I’m saying is that the good reviews outnumbered the bad ones by a lot.
MIB: Yeah. But, you know, I’ve received enough bad reviews for enough things, over the course of my career, that I had to sort of come to peace with both criticism and praise. And I have my own kind of internal measuring-tape for how I think something came out. And, you know, I think that book came out well. So I’m not overly concerned about the reviews. I think if I received a lot of bad ones from actual press, it would’ve really hurt. But I didn’t. I guess I was hoping it would sell more. It didn’t do terribly, but it didn’t do great. And I was hoping that it would attract a wider audience of people who didn’t know who I was. And I don’t know that it did that, either. I think my first book, My Custom Van, did better and it’s not as good a book. So that’s a bummer.
I recently heard you on Howard Stern’s radio show, talking about how your books hadn’t sold as well as you’d hoped. Is it any consolation that publishers want you to write more books and that you did receive plenty of positive feedback?
MIB: Yeah. It is. I’ve always maintained that I only need the books to do well enough that they want me to write another one. So, by that gauge, they’ve done fine, because they keep letting me write more books.
Speaking of radio shows, can you tell me a little bit about the recording of your This American Life piece, which was about the death of your father? Was that an emotional experience for you?
MIB: It was. I was out to dinner with [Sleepwalk With Me author and comedian] Mike Birbiglia, who’s a friend of mine, and he introduced me to Ira Glass, who was there too. And I told Ira I was working on the book and Ira wanted to know if he could see something, maybe for inclusion in the show. So I sent him that chapter and he liked it, so I went in to record it. And yeah, that was before the book came out and we did it all at once. It was in a tiny booth at his office and I just read it through. Pretty much right through. Maybe a couple things required me going back, if I flubbed a word or something. And yeah, I was a little emotional, because I’d never read it out loud and that’s different than just writing it. It activated a certain amount of grief in me. And it was cool, I was glad to do it and people certainly listen to that show. Writing about my dad’s death was hard, and took a while, because I’d never really written about it, or even discussed it much. It was hard to put that experience into words because any death is so fraught with complicated emotional weight. I wanted to excavate as much as I could from the experience without getting maudlin or too heavy. It took a long time to feel like I had gotten it anywhere close to where I wanted it to be. Still not sure I did.
I’ve definitely heard a lot of people mention that your piece was very emotional for them.
MIB: Well, that’s nice to hear. I’m glad. I’m glad people responded to it.
And did you feel like the cover of You’re Not Doing It Right accurately represented the book? How was that conceived?
MIB: Yeah. I thought it represented it really well. It’s meant to be a little bit funny and a little bit not funny and I think it accomplishes that pretty well. That photo was actually taken from my second album, called Very Famous, and I got some mockups for the cover for the book and I didn’t like any of them. So I suggested they used that photo and they agreed.
This morning I was thinking about your first book, My Custom Van, which is a great collection of humor essays. That book was absurdist, while your memoir was serious. It seems like you skipped a big step. Did you ever consider writing something more in the tradition of David Sedaris? The day-to-day escapades of Michael Ian Black.
MIB: Well, I think there’s a lot of people trying to be the next David Sedaris and probably a lot of people better qualified than myself to do so. I would like to be the next David Sedaris in the sense that most of his life involves wandering around various European metropolises, sipping coffee, waiting for [his boyfriend] Hugh to return from his job. And then occasionally going overseas to read from his books in front of packed audiences. In that sense, I would love to be the next David Sedaris. But he’s already such a good David Sedaris, it seems unlikely that anybody, including myself, is going to come along and fill those shoes. I don’t know who I am as a writer. You know? Which is an unfortunate thing to admit when you’re 42 years old and writing books. But my interest in writing has a lot to do with figuring out that question. And not so much in continually sort of rehashing the same thing or the same form, over and over.
It’s interesting hearing you say that because — while you mention you don’t really know who you are as a writer — your writing is so strong. In My Custom Van, you have such a great ear for dialogue and interior monologues and your word-choices are spot on. You make it look easy to write the funny stuff. Did you have to labor over that book, too, or was it more of a natural fit for you?
MIB: Well, My Custom Van in particular, which is just a series of stupid essays — and I don’t mean stupid in the self-denigrating way; I mean they’re really stupid in a funny way, I hope — was in a way, really easy. But in a way, it was a compromise with myself. Because I kind of didn’t want to write that book in the form that it took. Initially, when I first decided to write a book, I thought, I’ll write a proper book that has a beginning, a middle and an end. And I found myself incapable of doing so. So My Custom Van became my compromise with myself which was, “All right, you said you’re going to write a book. Write a book! It doesn’t matter what form it takes, just write a fucking book.” So that’s what I did. And so when it came time to write the next one, I vowed that it would be more of a proper book and would take things a step further in every way. And so that’s what I did.
One of my favorite things about My Custom Van is how many different approaches you take in writing a humor essay. You use open letters and lists and you mock various genres like erotica. Did your sketch-writing experience help bridge the gap into writing humor essays?
MIB: Yeah, I think it did. It was probably easier for me to write that kind of book than it would be for somebody who had never done any sketch-writing. It was a really fun book to write. It was a pretty joyful experience because it was so easy. I would just sit down and write one [essay] every day. Or try to. And it went pretty smoothly and pretty quickly.
It seems like you used long titles to box yourself in, to write yourself out of corners. Like your essay, “Using the Socratic Method to Determine What It Would Take to Voluntarily Eat Dog Shit For the Rest of My Life.” I’m guessing that you had that title and that you really did try to figure out exactly what it would take to eat dog shit for the rest of your life.
MIB: Yeah, that’s exactly right. That’s exactly how I wrote that essay [and] I feel like I got to it. I convinced myself to do that, if it was going to save lives.
Your Billy Joel piece just came out in a best-of McSweeney’s collection.
MIB: Oh yeah. I’m happy that they included it and I’ve had nothing but good experiences with them, but I can’t say I feel like I’ve won a medal or anything.
Do you have any desire to return to McSweeney’s writing? Or do you feel like you’ve moved on to different things?
MIB: I like doing that and probably will do it again. It’s just that I haven’t done it [in a while].
Did you have a favorite humor essay you wrote for My Custom Van?
MIB: Well, I don’t look at, so I can’t even really remember what’s in it.
Why? Does it make you cringe to look at your old writing?
MIB: It’s not that it makes me cringe so much, although sometimes it does. But it’s more like, I spent so much time on it that I have no desire to look at it ever again. Once it’s out there, I basically just want to wash my hands of it and be done. You know, I don’t look at my own acting if I can help it. I just don’t like to look back.
Speaking of looking back, do you keep journals?
MIB: I did journal for years and years, but they were the worst, most monotonous unhelpful journals in the world. Basically, my journals consisted of, “I like girls and I hope I make enough money.” Expressed in more or less that form for fifteen years.
So it’s not super helpful to dip into them when writing about your life?
MIB: No, and I looked back a little bit, but I found that whenever I looked back, invariably the thing that was most important to me, from whatever time I was writing about, weren’t mentioned in my journal. And I’m sure I’m wrong about a lot of those details, too, because memory is imperfect. But, you know, that’s what memoir is. It’s your version of a life. And my brother already yelled at me about things that he thought were wrong. And my wife yelled at me at things that she thought were wrong. But I think I got most of it right.
In the process of writing about yourself, it seems like it was important to you to be self-critical.
MIB: I didn’t want to be the hero of my story in the sense that I didn’t want to appear any wiser than I feel, or appear to be motivated by intentions greater than what is true - which is that most of what I do is motivated by fear. I didn’t want to appear smarter than I am or more virtuous. I just wanted to paint myself in a truthful light. Now, my own truth of myself might be more critical than other people’s, I don’t know, but I just wanted to try to be brutally honest.
I know that you made a decision not to live in Hollywood because you want to raise your kids outside of that environment. Do you think that decision has led you to writing more books, whereas that might not necessarily be your focus if you were in LA or New York full-time?
MIB: I think I’d be writing this stuff regardless of where I lived. I still write TV and movie stuff in Connecticut, too, but it’s generally more pleasurable to write prose, if only because nobody’s really looking over your shoulder.
You have a distinct advantage over other authors in that you have a performing background. You can turn your readings into events. Or you can go on The Late Late Show or This American Life without much hesitation and represent yourself well.
MIB: Yeah, I mean any performer, I think, has an advantage in that respect. I have an advantage in that I have a lot of Twitter followers. But my audience is, I think, fairly small in terms of people who actually give a shit about what I do. So all I’m trying to do is motivate those people. And they’re a lot like me, I think: they’re pretty lazy.
I saw a clip where you’re at Book People in Austin and, rather than just read from your book, you try to sell them insurance. Is the idea there just to promote yourself and that will, in turn, sell more books?
MIB: That was a sketch that was written for me that they wanted me to do. I did a reading and then afterward, we shot that sketch. So the people in that audience were all in on the sketch. The Austin thing wasn’t my idea. I probably should be thinking of better ideas on how to promote myself, but I don’t really spend a lot of time doing it. I really don’t know how to promote effectively.
I like the way you’ve promoted your books on Twitter, because it’s not over the top. I remember you saying, “I’ve given you more than 20,000 jokes for free. Now, every once in a while I’m going to mention my books.” How does Twitter translate into book sales with your 2 million followers, if at all?
MIB: I don’t think it does. Or maybe it does for some people. I think it did for [comedian and author] Rob Delaney. But, you know, I think it helped in the sense that I made some people aware of it. But I don’t think that I really motivated a lot of people to buy it or else it would’ve sold more.
I wonder if it’s the fact that Rob Delaney’s book sort of ties into what he’s doing with his Twitter account. His book has more of a humorous bent, whereas you wrote more of an emotional memoir.
MIB: Yeah, maybe, I don’t know. I wish I had a better grasp of how to do anything in terms of promotion. Because I certainly try. I certainly am willing to whore myself out, whenever and however. But it just doesn’t translate to sales.
What about all your time spent on Twitter: Do you find that some tweets lend themselves to bigger ideas that you can explore?
MIB: Every once in a while. I try to keep track of the ones that do. And then inevitably when I try to expand on them, it’s not so great.
Briefly, on America: You Sexy Bitch, what was the goal of the book when you broached the subject with Meghan McCain?
MIB: The goal was to write a fun and funny political book for people who don’t like politics, and hopefully show that it’s possible for people with differing political viewpoints to go out, get drunk together, have adventures, and a great time without choking each other to death. We accomplished our goal, although there were many times when Meghan’s hands were firmly clenched around my throat.
Could you have co-written this with any other conservative, or was there something specific that you liked about Meghan? Like her open-mindedness?
MIB: Maybe, but it was my trip with Meghan that opened my eyes to the truth that conservatives tend to be more fun than liberals. They just are. Because they do not give a fuck. That could certainly become a fault, but it’s a better fault than liberals, who gave way too many fucks.
Do you feel like she swayed any of your political thinking or vice versa?
MIB: I think we swayed each other here and there. She definitely opened my eyes to the other side’s thinking about the second amendment, and I convinced her that everything she believed was wrong.
It seems like a lot of your career is built on saying yes. Something like this comes out of the blue and you’ll try it and see how it goes. This is a perfect example.
MIB: Yeah. Of course. One, because I’m interested in things. And two, because I like money so much.
You’ve freely admitted that you don’t know if what you’re doing is funny — whether it’s crafting a joke for stand-up comedy, or riffing on a VH1 program or writing a book. Do you still doubt your ability to be funny when you want to?
MIB: Constantly. It’s something I worry about every time I perform in front of an audience. Maybe because I don’t know how to be funny. There’s no single way to do it. More than anything it’s about reacting, listening, and being relaxed and comfortable. But I never know if what I’m doing is going to be entertaining to anybody, least of all myself.
You’ve said that the things you never thought were going to turn into something end up being the most important things. Can you give me an example?
MIB: Twitter, for one. Those stupid VH1 specials, which probably provided me more exposure than anything I’ve done so far. The memoir, which I think changed the way people perceive me. Then there are the things that you throw everything you have into them and they end up going nowhere. It’s just a funny business. All you can really do, I find, is try to do a good job whenever you do anything and hope for the best.
Ultimately, do you feel like there’s a conscious effort for you to move away from things that are more absurdist and surreal and toward things that may not be as silly, but have greater personal meaning and lasting impact?
MIB: Yeah, I definitely made a conscious decision to do that a few years ago, again, as a way to break out of this character I’d created. Now that I’ve been doing that for a while, I feel like it’s OK to jump back into silly and surreal now and again, because I still love that stuff.
Jory John is the co-author of All my friends Are Dead, I Feel Relatively Neutral About New York, K is for Knifeball: An Alphabet of Terrible Advice and other humor books. He is also the editor of Thanks and Have Fun Running the Country: Kids’ Letters to President Obama. Jory has written for The New York Times, the San Francisco Chronicle, the Believer, McSweeney’s Internet Tendency and The Rumpus, among other publications. He’s on Twitter @joryjohn.