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I was a staff writer at The Onion from 2000 to 2012, and many of the events described here occurred during that time. Also, my memory can be a little fuzzy so if I get something incorrect please blame my oldest brother for dropping me on my head when I was a baby.

Many people have a romantic notion that working at a comedy outlet is like being part of the coolest tree fort there is, and there are moments like that. But mostly The Onion was a place where people worked hard and dealt with many of the same things that other office drones across the world have to contend with. 

We complained about our insurance, received “promotions” that were more a title change instead of a salary increase and got in screaming matches over which owl photo was the funniest. 

However, just because it wasn't exactly the tree fort of your dreams, that doesn’t mean it wasn't an interesting, and occasionally weird place to work. How weird? Let's begin with this…

No One Actually Knows Where The Onion Name Came From

Let's start with the fact that The Onion began as a newspaper in Madison, Wisconsin. For those of you not familiar, a newspaper is a thing made of paper that has words printed on it that you can either believe or not. “The Paper," as everybody who worked there during my tenure referred to The Onion, started in 1988, but most people didn't hear of it until the late 90’s, when The Onion debuted as a website. 

Everything about The Onion in it's early days was half-ass. Actually, that's giving it too much credit. It was sub-half-ass, probably somewhere around one-third-ass. I think the founders wanted to mainly make something weird and maybe earn money doing it. A chief revenue strategy in the early days was to line the bottom 1/6th of the paper with coupons for local Madison-area businesses that could be cut out and redeemed.

The Onion

Go ahead and cut these Uncle Jim's super savers out of your phone.

So yeah, no one bothered to record or even remember where the paper’s unusual name came from because no one knew or even gave a shit what it would one day become. One-third-ass. 

And the rest of the time, they were too busy doing what a lot of people did in Madison in those days, which was to smoke cigarettes, drink every beer you could get your hands on and listen to Killdozer.

Over the years, there were a lot of explanations bandied around regarding the name's origin. A popular one is that the owners were so poor that they ate only ate onion sandwiches, but that doesn’t appear to be definitive. 

The best explanation, imo, comes from former Editor-In-Chief Cole Bolton who said it was probably named to mock the UW-Madison paper, The Union, which honestly sounds like The Onion I know.

The Onion Didn’t Hire People From The Usual Places

The rule of thumb for a comedy career is to go to Harvard, work at the Harvard Lampoon then warp your way through fantastic TV writing jobs only to die in a wheelbarrow by age 50. 

But what do you do when you’re in Madison, Wisconsin trying to staff up your coupon-rich comedy publication and are far too polite to ask folks to move to your charming little city to work for cigarettes, beer, and Killdozer? You look in strange places. 

For instance, I was hired after making friends with the booker of O’Cayz Corral, the local punk rock club I cleaned before they opened for the night. 

Friends Of O'Cayz Corral Facebook Page

Chris Karwowski is a waaay better comedy writer than cleaner. -Ed

The booker knew The Onion's head writer and introduced me. I started writing headlines, and I soon went from getting notes to clean up vomit in the men's bathroom to writing comedy noted by my heroes. 

Others went similar “You look like you'll do” routes to becoming writers. My friend Joe Garden was hired after an editor took a shine to a funny sign he made for the liquor store he worked at. Head writer Todd Hanson was a dishwasher. Carol Kolb would say she used to “wash the elderly” for a living.

The Writers Room Could Be A Brutal Place

The Onion writers were, in general, a friendly bunch who quickly welcomed me in despite my cardinal sin of growing up in Illinois, which is viewed a step below Minnesota, and Wisconsinites feel Minnesota should have been traded to Canada even up for Quebec a long time ago. 

The process of creating an issue of The Onion began on Monday, when the writers gathered around a large table to read the week's headline submissions. Every story in The Onion begins as a headline, and on a typical Monday, we'd read hundreds of them.

Once you got used to the rhythms, the headline writing meetings were fun. But you want to hear about the BRUTAL details so yes, there were screaming matches, people throwing things, meltdowns and long-simmering grudges. 

Yet the real reason why it was brutal was that even if you read a real winner off your list and were just sure it would elicit a resounding “Yes! This headline is going on the front page immediately!” - that wouldn't happen.

Instead, the best you'd get was a smattering of understated nods and perhaps a murmured “Sure, why not?” 

If people didn’t like an idea there was usually just silence. If you’ve ever told a joke that landed to crickets you kind of understand. Now imagine after that joke failed you had to read twenty more headlines that you have no idea would work or not. 

I’ve seen more than one contributor who was REALLY confident that being in that room was the x-factor that would get more of their ideas into the paper. Soon, however, the devastating silence that followed one joke after another caused that contributor to get incrementally more pale.

I should point out this was not done out of malice. The simple fact is that, like many comedy outlets, The Onion is a volume game, and failure is far more common than success. There were hundreds of ideas a week to judge. After a while, you just want to get done as fast as you can. Laughter just slows things down.

The White House Threatened The Onion

Let’s get something out of the way, presidential goons did not come to The Onion offices with Mad-Max-grade baseball bats, “accidentally” break our owner David Schafer's priceless vases, tell us it would be a “shame if something happened to our nice satire business” and then leave. That did not happen. I wish it did, but it didn't.

What did happen was that an honest-to-god lawyer who worked for the highest office in the land told The Onion to stop using the presidential seal, or else. 

Wikimedia Commons

Solidarity - come get us.

We had been using the Presidential Seal for a weekly radio address by then President “George Bush” for The Onion Radio News. We didn't want to stop. We decided to fight back. However, The Onion certainly did not have the necessary legal firepower to win in a court situation.

This was pre-social media age, but we were already onto a simple truth: public shame has big power. So we released The White House cease and desist letter to the media along with our response. It totally worked

Also, former Trump fixer Michael Cohen once sent The Onion a cease and desist letter, too. It went predictably bad for him.

The Onion Had A Popular Friday Afternoon Office Party Called Whiskey Friday

Like all the best things, Whiskey Friday developed organically and then took on a life of its own. And that life was all whiskey, baby. 

It started after a few writers got into the habit of dropping by the lead designer’s office to chat, draw funny things on a whiteboard and sip a glass of whiskey. However, as it became more regular, more people started showing up. 

Since it usually started at around four and people in NYC often treat work like they'll die if they quit before five, complaints soon rolled in. Thus the get-together started to take place in the more private writer's room and then spread into other parts of the office, even going up to the roof on nice summer evenings. It quickly became a mix of The Onion staff, New Yorker cartoonists and various friends and well-wishers. 

The two Whiskey Friday events that stand out the most to me was the day Johnnie Walker sponsored a Whiskey Friday and the last ever NYC Whiskey Friday, held right before the NYC office closed up shop. 

The Johnnie Walker event was fun but strange. It was pretty unusual to have friendly corporate types show up at The Onion offices with enough free food and scotch to kill a buffalo, especially if that buffalo drunkenly wandered into traffic. 

The final Whiskey Friday was…a lot. I heard later that the business staff wanted to stop the party as they were afraid we were going to absolutely trash the place. It was rowdy but no one burned anything. Most of the large office was packed with friends, comedians and people who may have just heard about it. I just remember there were more dildos around the office than usual, and I don’t know why.

Umm, pretty sure last day in NYC & this stuff had something to do with it.

The Onion Writing Staff Tried To Buy The Paper From The Owners

In 2011, staff in New York were told their office was shutting down and anyone who wanted to remain employed by Onion Inc had to move to Chicago, where our companion publication, The AV Club, was located. The business side of the operation insisted that this move was absolutely, positively, not a way to consolidate the staffs into one location so that the entire enterprise would be easier to sell. We weren't convinced.

The Onion's Editor-In-Chief at the time, Joe Randazzo, wasn't either. He pulled us aside and said that a sale was 100% going to happen and then said it again during a meeting with the business and creative staffs. 

Our opposition to the move was not solely based on a mistrust of the business department. People had put roots down in NYC, Chicago has limited job opportunities for comedy writers, and so on. 

Then the creative staff of both the paper and video departments did something no one expected. It was so unexpected that The Onion CEO actually said, “I did not expect that." 

We reached out to private investors who were willing to put serious money on the table to buy The Onion. In return, The Onion staff would have received an equity share in the company, (something we wanted for a long time) and we could remain in New York. 

A sticking point was that the investors only wanted The Onion, not The AV Club which had been joined together for almost two decades. This offer was considered and rejected. 

Lo and behold what we knew what would happen did in fact happen! The company was sold to Univision. I don’t believe The Onion’s deal with Univision was that much more profitable than the one we offered. But it makes sense. Why sell it to the people who made the paper a nationally-recognized brand when you can squeeze out a few more pennies?

Since that time, The Onion has been sold again. Sigh.

For my part, I feel lucky to have been part of the ride - through the coupons, the failed headlines, and the whiskey I was part of something special, something no less than an authority than Bob Odenkirk called, “the best comedy writing in the country.”

And that's waaay above one-third ass.

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Thumbnail And Top Image: Wikimedia Commons/David Shankbone

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