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Jay Pinkerton's website makes me laugh. He's got pieces on there like Why I Probably Shouldn't Do Stand-Up , where Jay quips, "Why is it that the little black box is the only thing that survives a plane crash? Here's an idea: why not use the same stuff you make the black box with, and coat the passengers with it? Also, why crash at all? It just seems silly." I've spent many hours perusing his cache of scripts, articles, plays, and comics, and it's made me wonder: who is Jay Pinkerton?

What's your first memory of being able to make people laugh?

High school. I was a really skinny kid and I learned quickly that I wouldn't get the crap kicked out of me if I was able to make the other person look stupid first. It was more of a defense mechanism for me. The influences I had at the time were the Bloom County cartoons and Kids in the Hall. They awoke the sense of being funny in me.

What sort of forays into humor did you have before high school?

I wanted to be a comic strip writer- Peanuts, Calvin and Hobbes, and that sort of thing. My first love was buying those books. Eventually, I realized that you could make a lot more money just writing it than having to draw them all day.

Did you make your own comics?

I did, and they were awful. It was one of those things that, as a child, you think are awesome but, in retrospect, they don't make a lot of sense because a six-year-old is writing them. I had this detective series called Hot and Ham. It was a blatant rip-off of Archie Comics. They went around and solved crimes in a van. It had an Inspector Gadget vibe to it as well.

What were you like in school?

I was a quiet kid. I didn't have a large group of semi-friends, just two really close friends. We'd walk around the schoolyard during recess, talking, and telling each other jokes. We strenuously avoided things like sports and tag. It was more about trying to make each other laugh.

Were you incorporating humor into school assignments?

There was a science project where we had to write about animals that would live on a hypothetical planet. We were supposed to write about what they'd look like and what they'd eat. I made this cute hamster looking creature and described all of the adorable things it did, and then I invented another animal whose sole purpose in life was to eviscerate the cute hamster. It was all about trying to get a reaction from people.

Did you ever get in trouble because of an assignment that you did for school?

No, but I did get in trouble by trying to get people to laugh with pretend notes, fake papers, printing stuff at home and bringing it in. That stuff would get confiscated. I got walked into the principal's quite a bit in school, but I got better at being anonymous the more I kept going. In high school, I was voted funniest person in school, which is a double-edged sword. You're not the most attractive or most likely to succeed, you just make people laugh.

What were some of the things you got in trouble for?

The most horrible thing I'd ever done, and I didn't even realize it at the time, was when I went to camp and there was this girl with bangs that went up above her skull. She was trying to do some sort of 80's punk/avant-garde thing. I made a lame joke, which was, "Do you get FM on that?" What I didn't know is that the joke made it around the camp in for four or five days and it was one of those things where I found out eight years later from her brother that she'd never forgiven for me for it. It's one of those things that teaches you about the consequences of the stupid things you might say off hand. I was more careful after that.

Were you in any clubs in school?

Not until I got to university. I became the editor of the campus comedy paper, called Golden Words. I started off as a cartoonist and worked my way up the ranks. I realized I could get a lot more done if I concentrated more on the writing, and that's when I became a comedy writer. For four years I went from being shocking to learning that you had to earn the shock on a joke and trying to craft funny bits. I became editor the last year and got in a whole lot of trouble, but that was by accident. Back then, we didn't do the mags by computer; you just took a picture of the flap and they sent the picture to get processed. We did a fake ad for a candy called Twenty-to-Life Savers. It was just an off hand joke about a candy you'd use in prison. There was an enormous black guy who was one of the prisoners and the problem was that since we'd photographed it and it was pre-computer the guy came out looking like this horrible caricature, like blackface. All you could see were the eyes, the mouth, and this horrible black figure. I was called up by the dean of the college and it was this huge deal. Another important lesson: it's always the last thing that you expected that you get in trouble for in comedy.

What sort of role did humor play in your home?

Not a lot, to be honest. I love my parents to death, but neither of them was very funny. If people call me funny, I don't know where I got it. In my home, the fact that they kept me reading was a formative influence. At a very early age I was reading comics like Bloom County, Peanuts, and then graduated to books. It was definitely a reader's household. My dad was an English major and later and English teacher.

Did you ever have your father as a teacher?

No, but I still meet people that did have him from time to time. When I was in LA I met someone who was a student of my father from Kingston, Ontario, Canada.

What sort of place is Kingston?

It's midway between Ottawa and Toronto. There were about a 150,000 people in there. It's a college town. It's actually the prison capital of Canada. We have more prisons than anywhere else. The only people to have ever come from there are The Tragically Hip, a big Canada band that no one seems to have heard of in the States.

Were there a lot of encounters with former inmates?

Every once in a while we'd get a radio bulletin that someone had escaped and that was the signal for us to lock the doors, close the windows, and wait until they caught them. Normally, they wouldn't hang around and try to get as far away from Kingston as possible. There was always that eerie sensation of knowing that there was a deranged killer out there, somewhere, and that hopefully he wouldn't be knocking on your door.

So there weren't ex-cons working at the McDonald's?

No. This was a maximum-security prison, so there weren't a lot of people getting out in three years to go work at McDonalds. These were people that get locked up for a while.

Other than humor, what activities kept you busy growing up?

I played rhythm guitar and was in a band in high school. That was the big dream. We were big into metal back then.

What was the band called?

We called ourselves The Greased Up Scotsman, which is a nod to a Simpsons episode where Groundskeeper Willie said, " There's nary an animal alive that can outrun a greased up Scotsman." Probably not the first band to be named after a Simpson's quote, and not the last either.

How far did the band go?

One or two live shows and that was about it. It was more for the fact that when you're in high school and all of your friends come to the show, you feel like a rock star. But there came a time when we had to admit that we weren't all that good.

What would you cite as things that have influenced your comedic sensibilities?

Bloom County was the first thing that I read that actually opened up my eyes. At the time, it was doing something completely different from everyone else. They were doing risqué jokes, dealing with hard topics, and doing it with a new comedic style. Comic strips at the time, and even today, are palatable and easy to digest affairs. Bloom County blew the doors open for me with the idea that he was doing whatever he wanted all the time. In high school, Kids in the Hall were a huge influence on me. They were doing crazy, non sequitur humor. They were dressing up like women, doing sketches about absolutely nothing, didn't worry about having a break away hit character, they were just doing it to make themselves laugh. It was something that they weren't doing for any other motive than to be funny. The only other big influence was Mystery Science Theater 3000. We didn't get it in Canada, so I tape traded with people. So every couple of weeks I'd get a stack of tapes to get through of this hilarious show from Minnesota. I felt more of kindred spirits with them because they were Midwestern, had more of a quiet, polite, Canadian sensibility than a lot of the comics from New York or LA.

The idea of writing something that you think is funny rather than what other people will think is funny is very important, and sometimes people fall into the trap of forgetting that. What are some other traps that people should watch out for?

That's a big one. It's never to hedge yourself into a place where it starts to feel like work. At the end of the day, it's something I've always done when managing the website or just trying to make two other people laugh. I've invested so much time working a joke that would only be seen by two other people. You've got to do it for the love of doing it and if you're doing it for any other reason it will show through. Most of the success stories that you can point to in comedy are of people who followed their muse did it because it was hilarious and it was something that needed to be said. The people that are trying to second-guess, who are saying, "Ninjas are funny this year so let's do Ninjas," or pirates are hilarious, let's do that, or let's bash Bush because that's hilarious. That shows through as well. You can tell when a show's taking a down turn when there's more re-treading of what they think the audience wants rather than what they'd like to do.

What are some stylistic obstacles that you're conscious of overcoming?

I don't want to be known as the guy who just does comics or the guy who just rants about the bible. If I start to feel like I'm re-treading, I'd rather not update the site for six months until I come up with some fresh ideas. That doesn't make for an incredibly popular website because, ultimately, it's about volume. People need to get their fix and move on to the next website.

Do you think that the Internet has replaced the print magazine as a source for literature?

It's certainly taken down the life span of how long something remains fresh and funny. If you do something innovative, there will be fifty imitators within three days, within five days there's two hundred, and within a week it's already a cliché. The Internet has made it very tough to be on the cutting edge. I think there will always be a place for the print magazine. There's an air of legitimacy to it- of being in print, of being able to hold it in your hand, that it's been edited, and gone through an approval process. With the web, there's always that perspective of it being amateurish. It's a stigma that's not over come easily. I don't think the web will ever replace print mags, but it will hopefully one day be seen on equal footing.

What did you study in college?

English with a classics minor.

Did you take any creative writing classes?

No, the big thing I learned was that you learn better by doing than by being taught it. If I had any advice for anyone interested in writing, my advice would be to write. I learned more in three years working on a magazine and learning the hard way to do something rather than someone telling you how to do it. A classroom can't tell you how to write like yourself as best as you can.

Did you find your college experience to be helpful in your career as a writer?

I thought it was helpful in terms of the networking I did and the extracurricular activities I was in. Certainly, just having to write so many essays, having deadlines to meet, and coming up with new ideas on a regular basis. In terms of the actual subject matter, no, not really. If I had to give someone going for an arts degree any advice, it would be that they should be looking for a trade because we really don't need any more English, film, or feminist studies majors.

When did you move to LA?

I was in Toronto for a good four years. I entered the cubicle world and did what most art majors do: I became a high-level secretary. I wrote proposals for staffing companies and always treated the comedy writing as a hobby. It was just something that I did in my spare time to amuse myself. I stuck with it because I enjoyed it so much in college that I couldn’t imagine myself not doing it. I eventually had such huge piles of writing on my website that I started submitting it. The National Lampoon wrote back and wanted to use it on their website. I went from writing the articles, to writing and laying out the articles, to writing, editing, and laying out the articles myself so that by the time National Lampoon needed a new managing editor I was the obvious choice because I had been doing it for so long. That's when I got the invite to come down to LA. I had to sell all my belongings or move it into my parents' garage until it was down to one suitcase and moved to a completely new country. I was twenty-seven at the time and it seemed like something I'd regret not doing if I didn't give it a shot.

What was the worst letter of rejection that you've ever gotten?

This may sound vain, but I've never gotten a letter of rejection. It's simply because I went so long before starting to submit pieces that I was spared the pain of having my worst stuff turned down. By the time I actually started submitting stuff, it was universally accepted.

How long have you been a reader of comics?

Since I was five. I've been a huge Batman fan as young as three. I remember my parents hand making a wooden puzzle for me because we weren't that rich. Hand made presents for Christmas were a big thing back then. My mom drew a picture of Batman and my dad cut it out with saw to make me a puzzle.

Do you have an extensive collection?

Moving from LA to New York has taught me to take it light. When I was in Toronto I had a growing collection, but now I use public libraries and borrow when I can. I'll never make the mistake again of selling off whatever I own, and boxing it off and having people watch it for you is too difficult. Once you've moved to two or three different states in a single year, you learn your lesson.

What is it about superheroes that you find so interesting?

The idealism of it and the humor in perverting that idealism. Heroes are, to some degree, a reflection of who we've always wanted to be, especially if you're a gangly young teenager.

That's popular on TV.

Exactly. There's the Venture Brothers, The Tick, and all that stuff. I'm trying not to retread old ground. I did a comic recently called The Four Science Fellows and I got all of this great fan mail saying, "I loved the villain in it. It reminded me of The Monarch from The Venture Brothers." It's a complement, but there's nothing worse than hearing, as a creator, "I love your work because it reminds me so much of someone else's." I'm moving away from the superhero stuff and looking at other genres: jungle mysteries, detective comics, and stuff from the 20's and 30's.

Have you encountered any difficulties because of copyright issues?

Yes, insanely so. Marvel contacted me about The Spiderman comics and emphatically told me I should take it down. I try to avoid newer characters and comics. I try to go after the older stuff that's no longer in the public consciousness, so I can have some fun with it and maybe cast a new light on it, reminding people why it's so good.

A lot of my stuff takes a long time to do, probably longer than if I drew it myself. I know a lot of Internet people who do do this stuff and they just white out the dialog and put in their own stuff. I take various elements from different sources. One character from this comic, the background from a comic twenty years later, a gun from a comic ten years after that. People think it's just a page I grabbed, but a lot of it is hours and hours of tedious busy work.

Comedy doesn't get as much attention in print as gardening or even cigars. Why do you think that is?

A lot of that is the Net. I think the reaction is to do stuff that can't be turned out in a day. To hire artists to do really good spoofs, comics, to get interviews with people that you couldn't get if you were just a blogger. Cracked is highly aware that there's a lot of great talent out there turning out a lot of great comedy and there's no reason to compete with that in print.

Outside of Cracked and your own website, are there any projects that you're involved in?

I've always wanted to do a book, but I haven't had the time. It's something I'm hoping to do in the next year. Whether it's a collection or work or a whole new idea, I'm not sure. I'd love to sit down and do something big. If you look at all the stuff I've done, it's all small stuff. I'd really like to sit down and try my hand at a larger narrative.

Visit Jay Pinkerton online and peruse his archive of hilarity.