Interview With Chris Bucholz

Some of my readers will know I occasionally write freelance articles for the comedy website I love Cracked. It’s one of a very small handful of places where writers with no professional experience or industry connections can get their writing read by millions and get paid to do it. But I might never have ventured to check out the site if it hadn’t made a killer first impression on me in the form of an article by Cracked columnist Chris Bucholz, called How to Win a Fight Against Twenty Children. It was, as the title suggests, a practical guide that considered, in hilariously comprehensive detail, the logistics of fighting a large group of children all at once. Chris Bucholz has a certain proclivity for writing about these less visited areas of the comedic spectrum. His work is usually at its funniest when he’s covering a subject that no one realizes has been severely under-explored until he explores it. He’s the one who thinks about how Kevin McAllister from Home Alone would do in a zombie attack or how completely unfair the scoring system is in the fictional sport of quidditch. In this interview, I ask him about his history with Cracked and his writing process, among other things.

Brendan Bourque-Sheil: How did you originally get involved with

Chris Bucholz: I was basically just this guy who hung around on a couple comedy forums, specifically and I was posting little comics and stories that were getting pretty good feedback, and when Jay Pinkerton took on an editor position at Cracked, he invited me to start submitting content. No-one’s been able to figure out a way to make me stop ever since.

BB: You’ve been with since 2006. What has it been like watching it grow into the megasite it is now?

CB: I’m a freelancer, and from my perspective, the process of putting bum jokes into a word processor hasn’t fundamentally changed much in the past six years. But when I think about it, yeah I guess the site’s success (and my small part of it) is a little source of pride for me.

But we are just talking about Internet success here; it’s not like I can’t go to the store without being hounded by the paparazzi. Yet.

BB: How has creating weekly content for Cracked, every week for six years, changed the way you write?

CB: When I was starting out, I was far more interested in getting jokes down first, then crafting the article around that. That process has almost completely flipped now, with the points and arguments getting laid out first, and only then getting prettied up with the descriptions of funny sex acts.

BB: Describe the process of getting your average weekly column together.

CB: Throughout the week I read news sites, blogs, and otherwise try to stay plugged in to what people are talking about. I fill a little text file with ideas about possible columns, so that when it’s writing time I’m usually not grasping too much for a topic.

After that I decide how I want to frame it (lists, fake interview, short story, etc…) and then start outlining the points I’ll make. The first draft takes the longest, and will involve really heroic amounts of procrastination. It’s also, for all that work, not that funny yet. It’s the second and third and fourth drafts where pictures get added, the jokes get refined, and things start getting funny and rude enough that I’d be reluctant to show it to my parents.

BB: How do you avoid burning out when you’re expected to come up with new content every week?

CB: Part of this is experience, and the confidence that comes with it. After six years, I know I can come up with the funny when I need to. And the other part is a sense of professionalism. It’s a job, and I do it, and I don’t complain, because it’s actually a pretty rad job.

BB: Do you ever have weeks when your column goes live and you still have serious reservations about it?

CB: Not any more. During the first year or so this happened a couple times, but I’ve since refined my process to the point where everything I put out can pass my own 143-point Laff Inspection. I certainly think more highly of some columns than others, but don’t have serious reservations about any of them.

BB: Michael Swaim and Daniel O’Brien have cited you as their favorite columnist. Who are some of your favorite writers on Cracked?

CB: Did they? I bet they were fishing for compliments in return. Nice try guys. That said, I do read and enjoy all of the other columnists, but if I have to throw out a name, I’ll plug Robert Brockway, who is both bonkers and delightful.

BB: Outside of Cracked, who are some of your favorite writers and creative influences?

CB: My biggest influences actually do work or have worked for Cracked at some point, namely David Wong, Jay Pinkerton and Seanbaby. In the unplugged world, I read Neal Stephenson, Iain Banks, Michael Chabon, David Mitchell, and a few others. I’m also historically a big Douglas Adams fan, although he hasn’t written much lately for some reason.

BB: You’ve written a series of practical guides for weirdly specific situations (being challenged to a duel, dealing with a murderous clone, etc). I’ve had trouble describing them to people because they’re really too unique to be compared to anything. How did you develop them?

CB: I stand on the shoulders of giants. Bad advice columns have been around for years in a variety of other contexts, college newspapers most notably. And Jay Pinkerton did a couple columns on very specific bad situations back in the early days of the site. I’ve just run with the idea, playing up the dialog aspect a little more, and establishing the weird co-dependent relationship between the unnamed advice giver and advice needer. They’re some of my favorite columns.

BB: You’ve come up with a lot of other unique premises as well (an elaborate note left on a car door, an apology letter that tells the story of a petting zoo fiasco, an interview with the fictional characters Bert and Ernie). You tend to be able to weave a lot of different kinds of jokes into these pieces and many of them even have story arcs. Do you normally come up with these premises first or do you develop them as a means of facilitating jokes and ideas you’ve already written?

CB: Premise first, always. Because the universe isn’t fair, these really good premises don’t come around very often, so I do try to take extra special care when writing them. And I’d like to think Bert and Ernie would take the same care if they ever wrote about me.

BB: What are some reasons you like writing for the internet?

CB: I get to write about basically anything I want, litter it with low brow jokes, and get an enormous audience for it. It would be hard to find a similar gig in traditional media, at least not until the New York Times gets a lot cooler.

BB: What are some bad things about writing for the internet?

CB: Not many downsides at all at this point. It’s impossible to explain to grandparents what I do. I guess that’s a downside. I’m not pulling in much of the 70-95 demo.

BB: In addition to writing for Cracked, you have your website Do you have anything else you’re working on right now?

CB: I’ve been Twittering and Facebooking like mad lately, because I recently developed an appetite for attention.

I’m also working on a novel, as is, I suspect, everyone else who writes on the Internet. Unlike everyone else’s though, this one is incredible and fantastic. When there’s more news to share about it, I’ll be sharing news about it like mad. You’ll probably have a hard time escaping it, actually.

You can read more from Chris Bucholz in his weekly column at


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