Away with Words

by Joe Berkowitz

  As he flourished onstage, though, Tim’s writing career also developed. He started submitting pieces to Brokelyn, where he would eventually become an editor, and which led to a trial run writing features at the Post. With his command of punny house style and habit of procuring great quotes, Tim was eventually hired on at the only newspaper whose pun headlines have been collected into a book, 2008’s Headless Body in Topless Bar.

  “It’s probably the thing that most makes us famous, and the thing that people are most interested in,” Margi Conklin, Sunday editor at the Post, told me.

  Anybody living in New York has felt the NYP effect before. It’s a phenomenon where something happens in the world and, whatever your politics, you absolutely need to know how the Post will approach it in shouty World War III font. You can’t wait to get near a newsstand to see. Will it be shockingly blunt, like telling disgraced Subway spokesman Jared Fogle to enjoy a foot long in jail? Or just as vitriolic but more compact, like the front page devoted to a steroid-abusing A-Rod that just read a-hole? The New York Daily News is a distant second for puns and audacity, but the Post is the paper whose headlines most regularly inspire headlines about those headlines.

  The puns aren’t restricted to the front page, either. Beyond the “wood,” an old media term for the lead headline dating back to the days when they were printed using giant wooden blocks, puns are peppered liberally throughout the entire paper. As Tim soon found out, they weren’t just encouraged; they were practically enforced. It’s no accident that almost every lede on every story in the news section usually has a pun or two in it.

  “All the writers are expected to know how to play with words in the body text, not just headlines,” Conklin says. “Some writers take to it more than others, but if you’re good with puns, that will probably help with your writing here generally.”

  One of Tim’s first assignments was about discounts on fitness deals for the New Year, and his editor sent the piece back because the writing “wasn’t snappy enough.” He then revised it, packed in fitness wordplay like “run to the gym” and “sweat these deals,” and the story ran. His editor appeared to share some core values with Punderdome.

  Because of the paper’s reputation, the fake Post headline has become a trope in movies and TV shows. Few manage to get it quite right, though. Margi Conklin remembers being appalled by the pilot episode of the Showtime series Billions, in which the Post devotes a front page to Damian Lewis’s character buying a place in the Hamptons using hedge fund profits. The wood reads beach bum. It’s sort of close but not quite right, like a clone of you who hates eating and never gets sleepy in the middle of the day. At least when 30 Rock did a fake Post headline, the writers doubled down on ridiculousness. In one episode, the family of Rip Torn’s character, Don Geiss, fights for control of his business, somehow resulting in the wood memoirs of a geiss-ha! (When Tina Fey’s Liz Lemon sees the headline, she adds that she’d have gone with geiss screams: son pay.)

  The reason editors are defensive about the paper’s pun headlines is because so much care goes into creating them. The copy desk receives designs for each page with an empty display area, the allotted space dictating how long the headline should run. Unlike at the O. Henry or Punderdome, electronic assistance is not forbidden. The editors use word association sites to spark ideas for common phrases, and the rhyming dictionary site Rhymezone to help twist them into something new. They use IMDb, Wikipedia, and digital thesauruses. But even with so much pun hardware, the editors sometimes still fall back on tried-and-true hacks like Domers do. In the same way the topic of musical instruments may more than once spur Jerzy to say “guitar asses in gear,” Post editors know that in a pinch, a plan for the subway might be “on track” or “derailed,” and if the story pertains to education, someone could be a “class act” or have a “teachable moment.” They’ll find a pun one way or another.

  When the copy desk writes most headlines, each of the eight editors works individually. It’s a different story when it comes to the wood, though. The front-page headline is by far the one that gets the most attention. Sometimes it takes a village to create, but even then it’s considered an honor to be the one who finally nails it. The higher-ups might have an idea already by the time the copyeditors get in at 3:30 a.m.; more often than not, everyone pitches in. The process resembles an overcaffeinated office pun competition as the group brainstorms variations on a theme. The ideas build as they bounce from person to person, like a chaotic game of Telephone, with shouting instead of whispering. The highest-ranking editors may have the final say, but when someone expels the perfect headline, everyone knows it.

  Brayden Simms, a copyeditor who competed at the Post’s Punderdome event in 2015, remembers his first time pitching the wood. (This is, unfortunately, not the kind of book where the phrase ‘pitching the wood’ can be uttered without pausing to reflect on it.) Brayden was the new guy on the copy desk the previous year, when Anthony Weiner was considering getting back into politics. The senator’s initial sex scandal had ushered in a golden age of headlines, solidifying his status as a godlike deity in the pantheon of puns. (The puntheon, if you will, and I totally understand if you will not.) Weiner was one of the great headline muses in the paper’s storied history. If his surname and infamy didn’t move you to high art, perhaps you were working at the wrong place. On this occasion, one of Brayden’s coworkers suggested weiner rises again, and another kept the Jesus riff going with res-erection. That’s when Brayden connected the dots. He felt a tad too bashful to say this particular idea out loud, so instead he emailed it to his boss. When that editor read the pitch, weiner’s second coming, he stood up and started a slow clap. This headline was technical perfection.

  “Sometimes it’s better to not overthink the pun,” says Deb Pines, another copyeditor who competed at the Post Punderdome. “You let words tumble through your head that you associate with the story, then a phrase might come to mind and you just fix it.”

  That was Deb’s approach when she nailed the wood on a story about a panicky JetBlue pilot. She’d already ruled out JetBluenatic and was struggling, until she remembered an earlier headline. It was a story about a flight attendant who had been so fed up with the plane’s passengers, he quit his job, grabbed a beer, and went down the plane’s emergency chute. That story’s headline was freaking flyer, which laid the groundwork for Deb’s eventual winner, this is your captain freaking. It’s one of her proudest professional moments.

  The first time Tim Donnelly was asked to help out on a headline, he felt like he was being called up to the big leagues. He was cultivating a reputation for puns at a place where a talent like that would not go unnoticed. After a year of working for the paper, he wrote a feature about Punderdome and even talked his editor, Margi Conklin, into attending the show. One day, Tim heard Margi and some other editors in the office struggling to come up with the headline for a story. They were pushing the half-hour mark, the unofficial limit for how long is too long to spend on a headline, when a voice very clearly said, “Is Tim out there? Bring Tim in.”

  The man who sometimes goes by Forest Wittyker cracked his knuckles and walked into the room. He was on hallowed ground. Every time he’d taken the Punderdome stage had been practice for this moment. But coming up with a headline is harder than coming up with a typical pun setup. The pun in a headline has to play off both the sound of the words and the direction of the story. Also, it has to be polished enough to seem obvious in retrospect. The ideal pun headline should make readers furious they didn’t come up with it first.

  In this case, the story was about a heroin-addled chef who worked at a fancy French restaurant. After a moment of consideration, Tim looked deep within and pulled out: smack my bisque up. It didn’t make it into the paper, but it earned a place on the wall of great rejected headlines—not a metaphor, there is a wall—and established an open-door policy for Tim to pitch going forward. While he never came up with the wood in his tenure at the Post, Tim spent the rest of his
time there helping out with puns as needed. When a bad review of the Minions movie required a very short headline, he was there (dumb “minion”). When a story about the opening of an international-themed food court at the Brooklyn Flea in Queens lacked a pithy headline, he came through (world’s fare). As much as he was now a part of the team, though, Tim eventually had to compete against his own colleagues at the New York Post Punderdome.

  The copyeditors he would be up against, including Brayden Simms and Deb Pines, were not performers—just like Tim himself before he’d started punning. Fred Firestone and Margi Conklin had accounted for this distinction when they teamed up to plan the event. They knew they needed a different way for the editors to compete. The solution was to have them skip the opening rounds and come out in the semifinals to do the wood onstage. A techie projected the Post front-page template onto a screen above the stage, like the bat signal, and when punticipants shouted their headlines, they appeared on-screen. That’s how Brayden and Deb found themselves doing an essential part of their jobs in front of five hundred people.

  The news story Fred picked for the semifinals involved two brothers fighting inside a McDonald’s. When the clock started ticking, the two copyeditors went into work mode, racking their brains for the most appropriate pun headline. After ninety seconds, they had three options. Jerzy and Ally had six. The first thing Brayden had thought of was extra assault. It was only after the buzzer that he came up with what he felt was the Double Quarter Pounder of this round, golden arch nemesis. Deb went first for their team, using mac attack. When it was Ally’s turn, though, she did arch enemy, pulling the pun out from under Brayden. During the middle of his turn, he came up with scrappy meal, which got a laugh, but not enough of one to win.

  “We were quick, but nowhere near as quick as the Punderdome people,” Deb says.

  She and Brayden walked away from the event with a new respect for Tim and the friends on whose side he’d competed. They instantly got the appeal that drew him to the Punderdome stage. As copyeditors, they’d both anonymously contributed Post headlines that had been covered on TV and talked about in subways, and bars, and office break rooms all over. This was the first time they got credit for a pun headline beyond the newsroom. It was intoxicating. Tim got that feeling every month, though, so when he had another work opportunity, coming up with the wood wasn’t enticement enough to stay.

  Back at Littlefield for the first Punderdome of the year, I do a whiskey shot with Ally and the Gwiazdowskis between rounds. Now that I’m out of the running, there’s no fear that whiskey will short-circuit my brain.

  In the first heat of the second round, the category is Celebrities, which should be illegal for the Gwiazdowskis, since they routinely play a celebrity name game on their podcast. Surprisingly, Jordan and Jerzy’s turn is kind of a nonstarter. They will be lucky to make it to the next round.

  “It’s intimidating to be up here,” says the Pundance Kid next. “There’s a lot of experienced punners here and I’m just the Paul Newman.”

  The thing is, even though it’s his first time, he doesn’t seem like the Paul Newman. Pundance looks very comfortable onstage and he’s got incredible timing.

  “Just trying to keep the Streep alive . . . as is her makeup team,” he says at one point, waiting just long enough into the audience’s mock-outraged laugh to apologize. He knows exactly what he’s doing.

  When it’s Ally’s turn, she goes even deeper into Woody Allen territory than before.

  “Is this whole self-deprecating thing working? I don’t know, time will tell,” she says. “If not, I’ll just dust-it Hoff, man.” She sounds almost on the verge of a breakdown, which is in keeping with her stage persona, but some reality may be filtering in, too.

  Daft Pun won his earlier turn with a run of celebrity puns, and momentum is still on his side. He gets a huge laugh with an actress who moonlights as a crime boss obsessed with clear wrap: Susan Saran-don. Then he keeps going strong.

  When the clap-o-meter comes out, Nikolai and Pundance Kid move forward to the semifinals. As everyone leaves the stage, Jerzy and Jordan look like that tense couple at a dinner party who makes other couples tap each other on the leg under the table.

  The category closing out the second round is Sports. Ariel is up—as part of a duo called Pundercats, rather than her usual P-Witty solo act. Both Pundercats wear sheepish grins due to their limited sports knowledge, and it works in their favor. Puns like “Kobe or not Kobe . . . ,” charm laughs out of every corner of the room. When Isaac does his turn next, he continues the sports-ignorance trend, and he absolutely destroys.

  “To me, a touchdown is sampling pillows at Bed Bath & Beyond,” he says. “To me, a free throw is when I find a small rug on the ground.” The response is monstrous.

  Tim is batting cleanup, and he goes the conceptual route again. He warns the crowd up front that he’s going to mix football and basketball puns.

  “I’m going to try to court some favor,” he says, “and I might be a little Bull-ish when mixing these, so stay with me while I Ram them down your throat.”

  The incoming laughs are tepid.

  In his green army jacket and gray wool cap, Tim is visibly sweaty. You can practically see him deciding to switch horses midstream and abandon the cross-sports routine.

  “Guess you’re not with me on the mixing of puns!” he says, jumping up and down as if to shake off the mixed response. When he apologizes if his previous pun was an offensive line, though, there’s a shift in the crowd. They’re back on his side. The next few puns in a row land, too, and there are huge cheers as he walks back to join the others. It isn’t enough, though. Pundercats and Isaac move on, leaving Tim in the dust.

  That’s the difference between a pun here and one in a newspaper. A New York Post headline needs to be in service of showing the angle of the article or making a point. Here, though, the most important thing is making the crowd laugh. Period.

  A weird thing usually happens in the semifinals at Punderdome. The performers start to look zonked out while the audience gets progressively more hyped. So it’s as if everybody knows the strain Nikolai’s brain is under when his pun for the category of Countries is one about the German version of the medical soap opera, Hamburg E.R., and it gets a big laugh.

  The Pundance Kid is still slick and composed when he rolls out his next set of puns.

  “My cousin is a personal Heroshima of mine,” he says, which is almost empirically unfunny. But then he follows it up with, “That joke might be the worst thing that ever happened to that city,” and the crowd cracks up.

  Jo mentions at the beginning of every Punderdome that success here is 90 percent how you present your puns, and this guy proves it more than anyone I’ve seen so far.

  When it’s Pundercats’ turn, Ariel is still going strong but her partner is flagging. Tracey starts out with a weak pun about “That rapper, Manila Ice,” and follows it up with “You better Belize it.” They have a hard time getting the crowd back on their side.

  Somehow, there is no distinguishing between the energy level of Isaac’s third round and his first, though. He makes a joint-holding gesture and says, “Anybody want another toke, yo?” and the laughter barely dies down before he follows it up with “Okay, if you don’t—does Tia wanna?” Everybody onstage is laughing, too, even Ariel’s Pundercats partner, Tracey, who looked bummed a moment before. “Oh no, you dropped the bowl,” Isaac says, thriving on this weed run. “Where’d the glass go?”

  The clap-o-meter gives Isaac a 9.5 and not a 10, even though the room is positively heaving with applause for him. Everybody boos the clap-o-meter.

  Pundance Kid gets a 9.5 also. He and Isaac will be sparring in the final round together.

  We’ve finally come to the most inherently O. Henry–like moment of Punderdome. This is when the ramshackle, summer camp talent show air intensifies into something more like a rap battle during open mic night at the Laugh Factory—8 Mile for people more likely to listen to a Ste
ve Martin LP than Eminem. In the early days of Punderdome, the final two contenders faced off with whiteboards like any other round, but this routine changed a couple years in. One night, Jerzy and Rekha were up against each other in the last round and got exactly the same amount of applause. The crowd then started spontaneously chanting “Pun-off! Pun-off!” as though they were all familiar with the O. Henry. Jo Firestone relented. She ordered Jerzy and Rekha to put their boards down and pun back and forth for two minutes or until one of them couldn’t go anymore. The topic? Butts. After two minutes of verbal assplay, Jerzy won and a tradition was born.

  This time, Jo chooses the Human Body, which means butts are again on the table. The two finalists square up, smiling. Isaac has been having a hell of a night and he’s triumphed here before. But the Pundance Kid has had a strong showing and the crowd likes him. It could go either way.

  Pundance strikes first, saying, “We’d better give these people a show, man, they paid an arm and a leg to be here.”

  Isaac nods. “If we go on too long, I don’t think they’ll be able to stomach any more.”

  “Should we even be out here yet,” Pundance responds, “or should we still be in-testin’?”

  As the two fire off and return each other’s shots, I start to realize how unprepared I am for the O. Henry. In a breakneck exchange like this, you have to have several puns stashed at your disposal every moment, like a quiver of arrows. Not only that, but the judges at O. Henry will actually step in and point out that “an arm and a leg” is not a true pun since that expression refers to actual bodily appendages. I’m not ready for that. I hardly understand how anyone is.