It’s a story as old as time itself: man dislikes his job, decides to pursue a career in comedy, sends a bunch of unsolicited work into The Onion, and eventually becomes editor of the world’s most popular satirical news site. Well, maybe it’s not that conventional, but it is the general career outline of newly-appointed Onion editor Cole Bolton. A former associate economist at the Federal Reserve Bank of Chicago and research associate at Harvard Business School, Bolton’s comedy experience was practically nonexistent before he joined The Onion as a contributing writer in 2006. But despite never once being a member of a college improv troupe, Bolton’s passion and talent allowed him to work his way up through The Onion’s writers’ room, until he was named head writer this past November, and then editor just four months later.
I recently talked with Bolton about his rise through The Onion’s ranks, his new responsibilities as editor of "America’s Finest News Source," and the impact of satirical news in today’s media landscape.
How did you get your start in comedy? What kind of writing or performing were you involved in before The Onion?
I was involved in zero organized writing and performing before The Onion. It was actually something that I was pretty terrified about. In college, I never did improv or really did anything that was organized comedy. It’s something I admired and decided later in life, after I graduated college, that it was something I wanted to pursue. I was never in an improv group, never in a sketch group, never wrote for an Onion parody in college. It was just sort of a decision that I decided, two years out of college, that I didn’t like where I was going in my life, and I wanted to do something that I cared about more, so I ended up just sending stuff in to The Onion, which is going to look bad when this goes into publication because it’s going to encourage a lot of people to send stuff to The Onion unsolicited.
But that’s exactly how I started, was sending stuff unsolicited to The Onion because I had actually read something about a former employee who got a job in Madison by sending stuff in until the staff sort of noticed, and that’s exactly what happened with me. I just sent stuff in pretty much every week for five months or so, and eventually I sort of replicated, completely by chance, one of the headlines that they were about to run, and sort of frantically wrote in being like — probably very pathetically — “Did you use my headline?” But it was just a coincidence. But they sort of noticed that I was sending them stuff, so they offered me a contributing job, and I worked my way up from there.
Do you remember what the headline was?
Yeah! It was, “NASA Announces Plans to Launch Seven Hundred Million Dollars into Outer Space" or one billion dollars or something. It was almost verbatim, actually. So it was a pretty lucky coincidence, and it caught their eye, and they gave me a shot, which is something we specifically say we don’t do. [Laughs] So we probably don’t want that too well-known, but you get to crack the story, so there you go.
So would you advise against that?
I mean, people can do it. The thing is that the comedy institution that The Onion is now versus where it was eight years ago when I did that. I mean, maybe it would’ve gotten noticed a little better then because there were more interns on staff. We do a lot of timely stuff now, so I think everyone’s just busier – maybe that’s not fair to the guys who worked in New York, who I worked with as well. I think it might get lost in the shuffle a little bit more now. But, I mean, if someone is exceptionally good, and they get in contact with us somehow, we may look at it and it could, in theory, work out for them. But it’s a very, very low chance. I’m just sort of one of the lucky few who made it through.
I was doing some research, and you actually studied economics in college, right?
Yeah, yeah! Where did you find this stuff out?
It was on your LinkedIn.
Oh yeah, my LinkedIn! I have a bountiful amount of connections. What is it now? Several million, I think. Something like that. I think I have about forty connections on that. [Laughs] I should do more with that.
You don’t actually have a big online presence, which is surprising for a comedy writer.
No, no. I’m not a big – I don’t like comedy. I hate comedy. [Laughs] I hate what I do. I don’t know how I got here. No, I’m not that big into that stuff. Maybe one day I’ll get into it, but now I just like doing what I do, which is The Onion brand of comedy. You know, being a big presence on Twitter, maybe that’s something I’ll do in the future, but right now it just seems like a completely ancillary thing that I don’t really want to be a part of.
But if you did look me up, then you probably saw that there are two other Cole Boltons out there. One of them is a fairly solid presence on Twitter, I believe he’s an amateur hockey star in Canada. He’s doing much more with the name than I will ever do with it. So kudos to him. And then there’s someone else who I believe is from Texas, who is in the Future Farmers of America Association, high up, and he looks like he’s doing great too, so I think I’m just sort of trailing far behind in terms of the Cole Bolton name. And it’s very disappointing to me, personally.
Yeah, because when you Google "Cole Bolton," the hockey player is the one that comes up the most. So you didn’t want to challenge him?
[Laughs] Yeah, there is a part of me that is really, really actually rather annoyed by this. Because I’m older, and I’ve gone pretty far, but I guess what it goes to show you is that the power of Twitter can give this guy – who’s probably a very nice guy, and I don’t want to dump on this probably very nice Cole Bolton. But I mean, I’m extremely selfish, and I’m extremely arrogant, and I want to be the Cole Bolton. And maybe, just maybe, this article will put me at my rightful spot on the top of the Cole Bolton pyramid. So, it’s all up to you.
Is your new position as editor just a way to become the more prominent Cole Bolton?
I hope so. Because then this kid’s going to go to the NHL and he’s going to be fantastic, and it’s going to completely ruin me yet again. But hopefully this is the launching point where I can, you know, take over the internet, much like The Onion is taking over the entire media landscape.
Could you talk about your progression from contributing writer to editor?
Sure. For the first couple of years, it was just headline contributing. That’s pretty much how everyone gets their start here. Just writing headlines. And we always start with headlines before the story. And then if you stand out, if you get some good stuff in and people start to recognize your initials, which we put after every headline in our internal system, they’ll ask you to start contributing to what we call "daily content," which is stuff like the American Voices and Infographics, and Snapshots, and if you eventually do well at that stuff, you can try your hand at an article every once in a while. Or you may get asked to apply to a writing fellowship, which is this thing – it used to just be a summer-long thing, but now we actually have it rotating the entire year, where we bring on promising contributors that we have, and promising people from the outside who seem to have a good grasp on The Onion’s voice, to come in and essentially be like staff writers for the time that they are here.
So what I did was I was a headline contributor for a year and a half or so, maybe closer to two years, then they asked me to join the daily content ranks. I did that for another two years or so, and eventually I got the writing fellowship in 2010. And after that, I started being a writer-at-large, which is someone who is essentially a staff writer who is not in the office. And then when I moved out to Chicago, I came on as features editor, because I had a long period of contributor, which was contributing to the features, like the American Voices and Infographics. Since then, I sort of rocketed with lightning speed up from features editor to head writer to editor now because of some opportunities that our previous head writer and editor-in-chief had.
You became head writer this past November, and were promoted to editor in February?
Yeah. I’m just that good.
So what happened to facilitate those promotions so quickly?
You know, that sort of just happened. I think I was sort of the natural choice for both of those, but that sort of happened in more rapid succession than I anticipated, but that’s because, you know, we had some guys who had been here for a long time who took other jobs – some really good opportunities that they had – and it opened up, and I was selected to fill in those roles. And now I’m editor. And it’s been a long eight-year journey to get here, and I’m pretty happy about it. I’m still not number one Cole Bolton, but I’ll get there.
What have these past few months been like for you?
I’m learning stuff. Becoming head writer really wasn’t that crazy of a change for me because I’d been editing stories for over a year, or about a year, and that’s part of the job as head writer is to do a lot of editing. So I was sort of ready to take on the head writer role, sort of lead the discussion in meetings and give notes to some of the younger writers and edit. The transition to editor, very recently, has been a little bit more of a change because that entails being the final decision on everything and dealing with management, and having to pretend to care about interviews that I might have with people who call up from the press.
[Laughs] Which we appreciate.
That was a dig at you, Jeremy. So that’s just been an expansion of a role. The, you know, managerial stuff and the business side that I hadn’t anticipated dealing with. But the editing stuff is sort of what I’ve been doing for a year and a half, so I don’t mind it. But it is, like I said, the final decision on everything is a little weighty, especially when you’re dealing with a very respected, what is it now, 240-year-old institution? [Laughs] 26-year-old institution, I believe. It’s sort of murky. So, you know, it’s a bit of a weight, and I know some of the people who were editor before me are fantastic people, who I’m just trying to live up to their legacy, because they were brilliant people, and I hope I can carry the torch as best as humanly possible.
During your time as editor, is there anything in particular that you want to accomplish? At this point, The Onion is such an institution. Is being editor just about keeping things on track?
I mean, keeping things on track certainly, but we want to continue to evolve. The media landscape evolves extremely quickly nowadays. There are new things on websites, new things on CNN, just the media in general has just gotten frenetic and crazy, even crazier than it ever has been. Things that you start seeing on sites that don’t even seem like news sometimes, like on The Huffington Post and Buzzfeed, start seeping and bleeding into somewhat legitimate sites, like what Fox News and CNN do. And there starts to be this warring between actual news and sort of this “info-tainment” type stuff that they do. And so what we have been doing is trying to keep a strong eye on all these things that have been changing with media and news and evolve as we always have along with the news. Like when we did our IFC show, The Onion News Network at the height of cable news. We started doing slideshows in the past year and a half, which is something that legitimate sites do all the time now. We just want to keep it as satirical as possible of these ridiculous outlets that call themselves news sources. And that’s sort of what we want to do, just keep that going. Crush all competitors in the media landscape. That kind of stuff.
Just complete domination.
Yeah, complete domination. We expect to subsume everything in the media landscape. Be at the forefront of all sorts of new technologies, send out a fleet of drones to brainwash people for ourselves and for our advertisers, stuff like that.
That sounds like an amazing business plan. As a writer for The Onion, what’s your personal creative process like? Do you sit down and brainstorm, or is your process something that’s constantly going on in the back of your mind?
I think it’s different for every writer, but for the most part, I think some of our best headlines are just things that pop up when we’re observing something in daily life or that just sort of come to us. But for the most part, we get most of our headlines by sitting down and writing, actually being very writer-ly about it. Sort of just sequestering yourself and trying to come up with headlines. Sometimes a headline comes to you fully-formed, sometimes it’s just an idea and you want to work over it, parse it, and rearrange it until it becomes a good Onion headline. The main idea generation all begins with headlines. When we actually brainstorm out stories, that’s in a group when we’re all together. But for me, personally, a lot of it is the absolute fear of deadlines that are looming, and that sort of prodding you into sitting down and trying to come up with funny stuff. I feel like that’s kind of common amongst most of the writers, is that we’re people who will push everything until the deadline and then we force ourselves to write good stuff.
Do you think there are keys to a successful Onion article, or is it just that whatever is funny works?
Oh no, I mean, a lot of times an Onion article can be like a formula. A lot of it is art, but a lot more of it than I think you realize is this precise science. We sort of know how they’re structured, what sort of joke will work well in a certain spot. You can’t just go into it if you think you have a funny idea and write about it and expect it to be a good Onion article. It takes years. Even people who think they know the Onion style. You just have to work on it for years. You get it down and you start seeing this thing on the written page as the construction of a joke, and you rearrange pieces and move it around like a puzzle. It sort of takes the romance out of it, writing the thing. But a lot of it is almost formulaic – not formulaic, the jokes are never formulaic, they’re always very cutting edge and original. But we’re sort of mathematical about it. There’s a very serious, very astute, very specific way that we go about writing our stories.
Approximately how many submitted headlines do you have to go through per week? And is it at all exhausting having to navigate all of them and figure out which ones you’re going to use?
Monday alone is when we do most of our headlines, and we probably get – just from the people in the room, the writers in the room, which is about eight people – we must get close to 300 to 400 jokes. And then on top of that, we have dozens of contributors, so I’m guessing we go through probably 700 to 800 jokes on a Monday. And then we have these timely meetings, these sort of timely headlines that come up throughout the week. So I’m guessing we probably go through a thousand headlines a week.
And that’s not something that is just me. The entire staff is around going through these and voting on them or not voting on them, for which ones we want to do. And it can be a bit of a slog sometimes, but it’s sort of a way to ensure that we always get something good, if we have that much stuff to go through. It’s very much a democracy here. We don’t typically run things unless they have pretty much everyone on board as an idea we all think is pretty funny. So it is an exhausting thing, and it’s exhausting every week, and not just for me as editor, but for everyone who has to sit there and listen to all these jokes. But it’s completely worth it because if you have this many jokes and you only pull out 20 to 25 a week, you’re gonna get some good stuff. So there’s a payoff for all this effort.
Was there more to that? Did you want me to be editor-y about that, where I have to make the final choice on everything?
Could you make it out to seem more like a dictatorship?
Well, I mean, it sometimes has to be. If people are divided on things, you need someone who’s like, “Yes, we’re doing this,” or “No, we’re not doing this.” Or someone who can say, “We’ve done something like this before.” Someone who has more of an archival knowledge about things. Or someone who can see that something might seem like a good headline at first, but if it’s written out would seem a little corny or not sustain itself. That’s part of being more senior, is being able to look beyond something that might sound like a good headline at first but would not work as an article. Or, vice versa, something that doesn’t pop immediately when you read it, but you know that it would be a satirical piece, a trenchant piece, something that would be really good to have on site, and would be wonderful for… I hate to say "The Onion brand." Don’t make me say that. But would be really good for what we do, our institution, for furthering The Onion.
So I think that’s sort of expected of me now, and which is something I’m glad to do, which is to be the person in the room who has that decision and can look at the headline and try to be as foresightful – is that a word? – as possible about how it will do as an article. Whether it will be good, whether it will bad, whether we’ve done something like that before. That’s how it’s changed as editor, is that I’m constantly aware of where it fits in the Onion compendium, this 25-year thing.
So it’s democratic, but you’re the center of it all?
Yeah. I think people regard me as a dictator and they should, and they cower before me, but they can make their meek little votes if they want to try to sway me one way or another.
During your time with The Onion, what would you say you’ve learned about satire and comedy writing?
You know, I think one of the things that always strikes me is that I started out doing this as someone just trying to get my joke in there, to see my joke. It felt extremely good to get a joke in The Onion, something that was super well–respected and something that went out to a lot of people. But in the past eight years, one of the things that’s been way easier to me now than when I first started is, immediately, you can see it ripple across social media. You can see a joke that you’ve written or a joke that you’ve edited or a joke that you had no part of and just really liked, you can see it on Facebook or Twitter or whatever, and you can see people’s reactions to it in real time. Which, a lot of times is awful, and I don’t want to do things simply because I think they’re popular; I want to do things because they’re satirical and because they’re good and because they’re funny. But one of the things it has done is make me see that some of the things that I write or that other people write really do seem to have an impact on people’s day, really do seem to make their days better, hopefully, or speak to a point which they believe, but maybe they hadn’t been able to articulate.
And so Facebook, in a way — and I hate saying this, because so many people on Facebook are these moronic people who just comment on anything before they read it — but you do see the people who are thoughtful about it and who share these things, and they thank us. We get these public feedback emails back too. I guess that’s what I’ve learned, is that even though it’s something I knew implicitly going into it, we do have this ability to touch a lot of people with our stuff, whether that’s in a good way, whether it’s brightening their day with a little fun joke, or whether it’s making them think about a social issue. I guess I’ve learned the immense scope, the power that I wield, and the weight that is on my shoulders with this new position. [Laughs] That said, I mean, we’re still mainly in this to be people who make each other laugh in the room and who just want to put out stuff that we really think is funny. But I’m just happy that it does make people feel better. Hopefully!
It’s personally a bright spot on my Facebook feed, at least!
As I was saying that, I was growing more and more horrified that what it would come down to if it was written down is, “He’s really happy about Facebook and that people like things on Facebook.” And it’s not about the likes, it’s about getting to hear those things that you would never hear when it was just a newspaper. You don’t get to hear people picking up the newspaper and laughing while they’re on the train. I mean, occasionally I saw that in Chicago when we still had a print edition. But to be able to see that and to see that we’re making people laugh, making people think about social issues, it’s really fantastic.
I mean, it can be a grind every day to write headlines. I know people will probably see that and be like, "You should be thankful, you son of a bitch." And I am very grateful for my job. But it can be a grind, having to write new headlines every day, and they have to be good, and if you don’t get one in every once in a while you feel demoralized. But then you do get one in, and if it’s something that makes a strong point or makes people happy and they share it with their friends and family, it feels fantastic. It’s instant validation for extremely self-conscious people who doubt themselves entirely, like our entire writing staff does. Insecure people who need validation. I guess that’s all what we’re looking for here, is personal validation.
That’s all comedy.
We’re all very sad people. But you’re right, it is all comedians. We’re all extremely insecure people who are constantly doubting ourselves even after we’ve done something good.
Jeremy Popkin is a freelance writer in Philadelphia. His work has been featured on Ology, Nerve, and Destructoid.