Seriously Funny

For Ben Karlin, walking away from success at Comedy Central’s The Daily Show and The Colbert Report was the logical next step in a career that’s been anything but cautious. What’s he up to now?

Enter the loft office on the third floor of a former Brooklyn factory, and before too long, your ears catch the subway noise that intermittently vibrates off the nearby Manhattan Bridge. Very quickly, your eyes go to the colorful index cards tacked to bulletin boards on wheels. “Creepy Guy Project,” “Bode Miller,” “Asshole Guys Who Look Like Jesus,” and “Things I’ve Learned From Women Who’ve Dumped Me” are among the titles written on the cards in black marker.

Those ideas are the core of why Ben Karlin ’93 decided to walk away from a job many consider to be the pinnacle of television comedy. It would have been easy to stay put. But Karlin had too many projects brewing that he didn’t have time to pursue while also keeping his eye on the ball as executive producer for The Daily Show and The Colbert Report. Karlin left the two cable shows in December 2006 and launched his own production company — dubbed Superego Industries — in September 2007. With a freshly inked HBO production deal, he’s forging a new career path developing ideas for television, movies, and the Internet that don’t involve riffing on the headlines.

Big ambitions? Yes. Super ego? Not at all. He offers to grab coffee for us and mostly ignores his cell phone — even though it chirps at a regular clip. That unpretentious attitude is refreshing, given that he’s been part of not one, but two, of the most influential forces in comedy in the last decade.

Karlin served as writer and editor for The Onion, the satirical newspaper born in Madison, before making the leap to Hollywood. From there, he became head writer and then executive producer for The Daily Show, Comedy Central’s nightly recap of current events that succeeds at making you think and laugh at the same time. He also co-wrote the bestselling America (The Book): A Citizen’s Guide to Democracy Inaction, as well as helping craft Daily Show anchor Jon Stewart’s material when he hosted the Academy Awards in 2006. “Basically, if you’ve laughed in the last ten years,” New York Magazine wrote, “Ben Karlin was responsible.”

This spring, Karlin has a new book out, Things I’ve Learned From Women Who’ve Dumped Me, which includes contributions from Nick Hornby, Stephen Colbert, and Andy Richter, as well as a foreword by Karlin’s mother (see excerpts). The anthology is a collection of essays that makes you laugh, but also manages to teach you a thing or two about relationships.

Karlin, who is also in his first year as a new father, sat down with On Wisconsin to talk about the book and life before, during, and after the fake news. The conversation, edited for length, follows.

On Wisconsin: I really enjoyed [the book]. … I was curious where you got the idea and how you recruited people, and if you gave them a specific “charge” going into it.

Ben Karlin: One year I was going to do a pilot for NBC, and I didn’t want to do a traditional, half-hour type of sitcom-type show. So one idea I had was for this show ... where every week’s episode was a failed relationship in the life of this guy who was learning a life’s worth of lessons. … They did not care for that. I thought it was a good idea. … I ended up doing something about a ski town, I believe.

I had the anthology idea and, fortunately, the last eight years or so, I’ve worked with a ton of really talented, funny people — a lot of my friends and people I know and friends of friends. So I just kind of built the list organically from people who I liked and thought were funny. I started out much more ambitious, thinking wouldn’t it be cool if I got Bill Clinton, you know? And wouldn’t it be cool if I got Michael Jordan? And then the reality of getting those people … at a certain point, I just said let me focus my energy on finding people who I actually like, and let the quality of the book be the quality of the book, and if it sells x amount less because it doesn’t have Bill Clinton on the cover, I can live with it, because at least I’ll be happier with the book.

OW: I was really impressed with how open everybody was. I mean, they’re really frank about their anxieties and insecurities and heartbreak — even yourself.

BK: That’s what I wanted. To me, the hard thing to do here is to not have it be something that was sappy or treacle or feel-good, but also not be something that was just cold and clinical and funny, but had no soul. So the challenge was, how do you have it be funny and have people be laughing, but also, when they finish an essay or finish a piece — not necessarily every time — but [they] feel like, “Oh, wow, I just got a little window into that person’s life or that experience,” or “Yeah, I felt that way”? … That’s what we tried to do on The Daily Show, really, is kind of connect to what people care about, but not be over the top in terms of [being] so broad that there’s no substance to the humor, or so serious that there’s no humor.

The point, however, is that upon leaving our college town — I’ll call it Eden to protect its identity from future pilgrims who may flock there to trace the origin of this very story — mistakes were made. Some were mistakes of vanity. Others of youth. Still others of the vanity of youth. Eventually, these mistakes would pile up and their weight would become too much for any one man, or relationship, to bear.

— Ben Karlin, from Things I’ve Learned From Women Who‘ve Dumped Me

OW: Was there a lot of editing, then, because of that, with some people? Did they go too far over the edge?

BK: No. … The hardest part about it from an editing standpoint was just reminding people that in some way the pieces had to be lessons. … There had to be some kind of takeaway that the author, either ironically or seriously, learned from this experience. … All I cared about was that it was something real and that, when you finished reading the piece, you felt that that was a true enough experience.

OW: When I first heard about the book, I thought, “Oh, this is going to be a ‘guy’ book.” But from when I read the opening essay, it really seemed to suggest that women have a lot to learn, too, and as a female reader, I got a lot more out of it than I had anticipated.

BK: The goal was to write a book from the male point of view that has — I don’t know whether you’d call it male humor — but just … is written by male humorists that, at the same time, does provide some kind of window into men’s processes and how they respond to things that would be interesting or informative for a curious woman.

OW: You’re pretty newly married, right?

BK: Yeah.

OW: Did your wife have any involvement in this book?

BK: Not really. The funniest thing is I didn’t know if it would be appropriate to dedicate [the book] to her, so I think it’s good you always have an out when you do a comedy book. ... You can always do a comedic dedication. [In this case, “This one’s for the ladies.”]

The original piece I wrote was actually about a woman I dated in Madison. … I started writing a story that wasn’t as intensely heartfelt, and it was more just a funny situation. It was called “If You Lie, You Get Caught.” … My co-editor, Andy Selsberg, who is also a Madison alum, he said, “If this is your book, you can’t do that” because he knew the story I ended up going with, he knew the details of that, and [he]said, “That’s the story you gotta write. I mean, you can’t put out a book with that title and not do that story.”

Photos of Ben Karlin's office space

Ben Karlin, working in his Brooklyn office (top), signed a deal with HBO last year to develop film, TV, and Internet projects. “You know that ten-year question or five-year question everybody always asks you — ‘Where do you see yourself?’ I’ve never had an answer for that at all because,” he says, “it’s like, I don’t want to know.”

OW: I’m wondering how you decided originally to come to Madison for school.

BK: I wish there was some kind of great, apocryphal-seeming story, but the truth is I really wanted to go to the University of Michigan. … When I started looking into colleges, I realized that I needed to apply to more than one college, so upon doing research, Madison kept on coming back as a place that if you’re interested in Michigan, you should really look at Madison. … And I got into Wisconsin. I didn’t get into Michigan. ...

I was on Cape Cod for the summer, working and just partying like crazy. … By the time I arrived in Madison for orientation, the week before classes started, I was really run down and feeling terrible. So we dropped off my bags at the dorm and went right to the University Hospital — where I found out I had mono — on the first day of my freshman year. But in spite of that very inauspicious beginning, I pretty much from day one loved the school.

OW: Did you have a sense of what you wanted to do? … Was comedy in the equation at all at that point?

BK: Comedy was actually integral to almost everything I did, in terms of when I wrote papers for classes, they were not always appreciated by the professor — but they always had a comedic bent to them. My writing, the way I lived, was more disposed that way, but I never articulated it in terms of “I want to be a comedy writer. I want to be a comedian,” or “I want to be an actor.” I never articulated a specific goal for myself at all. It was always much more massive, existential, like I want to be happy and I want to do things that I’m proud of. … I thought I wanted to be a sports writer, and I wrote sports for The Daily Cardinal …

Whenever a girl would dump my son — and he had his share of heartbreak as a boy — I would always say the same thing to him, “Those girls are all fools and idiots. They don’t know what they’re missing.” He would always say, “You’re just saying that because you’re my mom.” He had me there.

—┬áBarbara Karlin, Ben’s mother, from the foreword to Things I’ve Learned From Women Who‘ve Dumped Me

OW: In the Morton Years, no less …

BK: Exactly. … I lived through the Morton and the Yoder years, okay? ... So a lot of people from the Cardinal migrated over to The Onion, and I had always wanted to write for The Onion, but it was this kind of, it was like this mysterious thing. ...

My junior year, I had gone abroad and got this great gig at the Summer Olympics in Barcelona, and I was a stringer for UPI, and I just basically fell out of love with sports writing. I was like, this is not what I want to do, these are not the people I want to be spending my life with. … I’m going to contact someone at The Onion and submit some ideas.

OW: So do you remember what you submitted?

BK: The way they did it at the beginning is they had you submit a list of ideas, a list of Onion headline ideas. And if they liked it, they probably have you do another round, and if they liked it, they invite you to a meeting. … And at first, you just got invited to the ideas meeting, you contributed ideas, and if you kind of proved yourself, then you would get invited to take one of your ideas and write an article about it. And I’m sure if I looked back at that … all the ideas probably suck, but they were good enough at the time. Your comedic standards completely change. But that first article I did — I remember very well — was this terrible article. ... It was called “Bill Payment,” and it was an editorial arguing that because the Buffalo Bills lost the Super Bowl, the city of Buffalo should be destroyed.

OW: So for a long time, it just seemed like the trend story on The Daily Show was, “Oh, this is where people under a certain age get their news,” and I’m wondering what you thought of that.

BK: It’s definitely a type of thing that — if it were true — would be like a fantastic little irony, that type of irony that the news media loves more than anything to kind of advance. The sad reality is that it would be virtually impossible to get a true understanding of news and current events by watching a show like The Daily Show. You have to have some other context, otherwise you’re a reaction without the action, so then you have to figure it out. … I have no doubt that people who watch the show may walk away with some information or a take on something they may not have considered, but I would hardly call that a primary resource. … I know exactly why people want to say that to be the case, but it just can’t be. It’s not.

The grudge is a way to show you care, a way to stay connected. It would have been an insult to let what we had be downgraded to a mere polite acquaintanceship or even worse, nothing. The grudge required embarrassing, accusatory letters. It required sending blank e-mails. It required every meeting we had to be ambiguous and tense. It meant feeling sick when I saw girls who looked like her.

— Andy Selsberg ’94, former staff writer at The Onion who teaches English at City University of New York, from Things I’ve Learned From Women Who‘ve Dumped Me

OW: I also saw where you talked about having this experience of the “real” working journalists coming up to you and saying, “Oh, I wish I could do what you do.” … What did you think about that?

BK: Well, it’s weird for a couple reasons. ... Implicit in it is this idea that they are forbidden from speaking the truth, and that we somehow are allowed or unfettered. Well, you’re a journalist, [isn’t] part of your job to figure out how you can make sure that you feel very good and comfortable and proud of the news that you’re reporting?

OW: One of the things I had always thought about when watching The Daily Show was I just wondered if there were some days when it gets so hard to find the joke, because there’s just so much horrible stuff that seems to continue going on …

BK: The worst thing, really, was the repetition. I think that trying to find nuance and new takes on stories that were ever-present got very difficult, because the first challenge is to entertain ourselves. If we’re entertained, then other people will be entertained. … The hardest thing was not necessarily finding stories, but making sure that we found the joy or the funny or the irony or absurdity in, a lot of times, stories that had a really long tail.

OW: Something like Iraq, in particular?

BK: Exactly. … It was such an organic evolution from “what kind of stuff does The Daily Show do material about?” And then, okay, we’ll do it about this, and if we do it about this, here’s how we’ll do it. So by the time Iraq came around, we kind of had a system in place for how to deal with something like a war. … A war is not necessarily something like a plane crash, which is pure tragedy and just, you know, no humor to be found in a plane crash. But a war, you know the parts of the war that are tragic: innocent loss of life and corruption. … That’s not your instinct to tell jokes about. But the hubris of a person saying something you know not to be true, and there’s this kind of propaganda element, all that stuff, okay, it wasn’t difficult in that way.

The spring of 1991, my junior year, was an exciting time. I had a dorm room to myself. I was drawing a well-regarded daily comic strip for my school paper, and Our Troops had just finished kicking Saddam’s ass in the first Gulf War, setting the stage for the peace in the Middle East we enjoy to this day.

— Dan Vebber ’92, former editor of The Onion who has written for shows including Futurama and American Dad, from Things I’ve Learned From Women Who‘ve Dumped Me

OW: Let me jump ahead to where we are now. … I just want to get a sense of Superego Industries … I’m just curious what you can say that these cards [on your office wall] may involve.

BK: The idea behind this company was can you do a production company that develops material in a more interesting way than the traditional development process, which has been: you pitch an idea, they commission you to write a script, you write a script, they give you notes, they either don’t like the script or like the script, and maybe you make something and the whole thing takes a year or six months or whatever. The idea behind this company was — can we set up a company that is going to be able to do movie, TV, Internet stuff. It’s going to be able to make things on a small scale, kind of show our work in a way that it is a little faster and a little more interesting than the kind of traditional, linear development process.

OW: Did you pitch yourself [to HBO] in that kind of economical fashion?

BK: Totally. Absolutely. Listen, the fact is something like The Daily Show or Colbert, those shows are done at a fraction of the cost of Saturday Night Live or Leno or Letterman or Conan, because they’re using a basic cable model and they compete on the same playing field. So it’s already been proven that you can do work, especially in comedy, that holds up against much bigger-budget things. …We can do a company like that. … That’s like the producer part of me, just trying to figure out a way to actually do things. Because the worst thing about being a writer, especially in television or film, is that an overwhelming amount of the work that you do never actually lives in the way that it’s intended. You write a movie, and that doesn’t mean the movie’s going to get made. [Out of] the overwhelming number of scripts people write, a fraction — a tiny, tiny decimal fraction — get made, so it’s really frustrating, it’s very isolating and frankly depressing if you’re just constantly working on things that never really exist. … [With our model] maybe you get to shoot a scene from your script, and to me that’s more gratifying than having a closet full of scripts that I really love, but will never get made.

OW: You won an Emmy, which is obviously cool, but I’m wondering if there’s anything else that’s meant more to you. … When you’re working and you’re doing what you like to do, sometimes it’s the experiences that mean more, and I’m curious what those have been for you.

BK: As far as one singular, thrilling moment, there hasn’t really been one. There’s been a bunch of moments where you step outside exactly what you’re doing and being like, “Oh, wow, this is pretty cool. I can’t believe this is my life.”

I just had an experience like that where I was asked to consult on this book project that is happening in Spain. … I got to go to Spain for a few weeks, and I was with some really interesting people … and we’re traveling in incredibly beautiful places in Galicia in northern Spain, and we’re eating the best food and drinking the best wine and staying in the nicest hotels, and I’m getting paid to do it. And, I mean, that was two consecutive weeks of, “I can’t believe I’m getting paid to do this.” Just absolutely pinching myself.

OW: It seemed like stuff I read about when it came out — oh, you’re not going to executive produce [The Daily Show] anymore and you’re starting your own thing. … The tendency is that people are always looking for conflict in those situations. It didn’t really seem like there was one. Were your reasons just [that it was] time to do something new?

BK: When someone’s looking at it from the outside, they can’t imagine why someone would leave a good job that pays a lot of money and is prestigious and all those types of external things. But the bottom line is, you have to go to work every day, and you realize at a certain point that the most valuable resource that you have and the most precious thing is time. The time that you spend doing something is, by definition, time taken away from other things. …

We had achieved a tremendous amount at that show, and I’m sure that it will continue to achieve and be impressive, but for me personally, there wasn’t more for me to do there. … I also spoke about that honestly and openly with Jon [Stewart]. It just felt like the reasons why I would stay would not be the right reasons. …

I have zero regrets, zero misgivings. It was definitely the right move, there’s no hesitation about that. And so there really wasn’t a conflict in the sense of a battle or something like that. … I feel like it’s such a simple thing, but people have a really hard time understanding, because they only see, “Why would you leave a job if you didn’t have to?” …

A lot of people do [stay in the same job] — people do out of fear. People do because they’re afraid that they might not get something better, or they don’t want to be unemployed. Those are all valid reasons. I just have never, never made a decision — and that’s been partly arrogance on my part, I admit it — I’ve never made a decision based on, “Well, I’m afraid that if I do this, I won’t be successful.” I’ve never made a decision like that. I will bet on myself.

OW: I feel like a lot of people must ask you, “How do I get your job?” or “How do I get started doing what you’re doing?”

BK: The hardest thing about having a career in the arts is that there isn’t really an official path. … It’s this really weird combination of you have to have talent, and then you have to have a certain ambition, and then you have to be willing to kind of develop your skills. … There is some luck involved or, not necessarily luck, but recognizing when an opportunity is a good opportunity and what it means. …

It’s so hard because, again, it’s not like I set out a path when I was in college and said in twelve years I’m going to be sitting down, hopefully, being interviewed by On Wisconsin Magazine. … You know that ten-year question or five-year question everybody always asks you — “Where do you see yourself?” I’ve never had an answer for that at all because, it’s like, I don’t want to know. …

If you have an impulse, if you have a desire, if you have a passion — especially if you’re young — take the time to at least explore it and figure out how it can apply to your life. … If you have an opportunity, you can live cheaply. There’s a way that you can kind of explore your passions and your interests, and I think you at least owe it to yourself to try. … That way, you don’t become the type of person who has a career and then goes up to people and says, “I wish I had your life.”