BuzzFeed Is Revolutionizing the Crossword Puzzle

Led by puzzle wunderkind Caleb Madison, a new generation of crossword constructors is pushing the boundaries of the word grid

Caleb Madison, 22, is BuzzFeed's new puzzles editor. (Photo: Celeste Sloman for Observer)

Caleb Madison, 22, is BuzzFeed’s new puzzles editor. (Photo: Celeste Sloman for Observer)

On a recent afternoon at BuzzFeed’s fifth-floor headquarters in New York, Caleb Madison was making a crossword puzzle. “I realized a crazy thing,” he told me, drawing up a half-completed grid on the screen of his laptop. We were sitting in the bright BuzzTeam conference room, and a photo of a sloth, an animal whose cuteness the company loves to fetishize, was staring impassively from the corner. “‘KATNISS EVERDEEN’ and ‘HERMIONE GRANGER’ intersect at their middle letter,” Mr. Madison said, his mind racing. “‘COLLINS’ and ‘ROWLING,’ ” he added, “both intersect at an ‘I.’ ”

Despite this fortuitous bit of lexical crisscrossing, Mr. Madison was having trouble figuring out how to properly incorporate all four words into the puzzle—themed, as you may have guessed, around The Hunger Games and Harry Potter. “It would have to be three-dimensional,” he mused, somewhat disappointed. “I don’t know if BuzzFeed has the technology for holographic software just yet.”

As BuzzFeed’s new puzzles editor, Mr. Madison, a recent Yale graduate with dashing brown hair and big, expressive eyes, has thought a lot lately about how far one can stretch the possibilities of the word grid. For the past couple of months, he’s been vigorously assembling a collection of games that will constitute the site’s new daily in-house crossword. The first week is queued up, and it will roll out, most likely, in mid-October. When we spoke, Mr. Madison had about 30 puzzles in the docket, most of which he was still fine-tuning.

The fact that BuzzFeed is putting out a daily crossword may come as a surprise to those who associate word games with bespectacled baby boomers. But about 50 million people in the United States do crosswords, and over the past couple of decades, the audience for puzzles has skewed younger.

The 2006 documentary Wordplay introduced a generation of teenaged viewers to the joys of cruciverbalism, and there are blogs and crossword clubs and tournaments all around the country. The Wall Street Journal recently started publishing a playful daily crossword. And perhaps most importantly, a robust independent puzzle universe exists in which talented constructors like Peter Gordon and Matt Gaffney show off their wares, week after week, for a subscription-based audience of expectant word hounds.

That is the world Mr. Madison is tapping into for his BuzzFeed puzzle. Unlike the typically buttoned-down New York Times, which has to pass the “Sunday breakfast test” so as not to alienate readers (and shies away from employing modern slang terms), indie puzzles are by turns raunchy, sarcastic and of their time—gonzo, in a word. (Sample clue: “Deal with one’s period, perhaps?” Answer: “EDIT.”) “We’re kind of like craft beer makers,” said Brendan Emmett Quigley, 41, a crossword constructor whose puzzles will appear on BuzzFeed. And by bringing the indie sensibility to a mainstream platform, Mr. Madison has the chance to redefine the crossword—a totemic image in American culture—for a new generation of solvers.

In a way, BuzzFeed, which rakes in around 200 million visitors a month, is a natural fit for these new puzzles and the people who love them. The site’s homepage is a curated grid of randomness—sloth news slotted in beside political dispatches—just like a crossword, which is always subject to the whims of alphabetical probability, never mind how witty a constructor may be. “Doing a puzzle is a very social activity—like you might do it with family or friends,” said Jack Shepherd, a BuzzFeed editorial director who brought Mr. Madison on. He heads up the company’s Buzz team, which is responsible for putting out viral content like GIFs and quizzes and animals listicles. “I like bringing that to BuzzFeed, which is a very social company.”

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Most crossword constructors display an aptitude for wordplay early on; it’s an avocation that seems to require precocity, and Mr. Madison, raised in Manhattan, was as linguistically precocious as they come, solving Metro and am New York puzzles in middle school on his subway commutes and quickly transitioning to the Times. “I liked the screen that it put on things,” Mr. Madison explained. “The way it organized information that I already had in my head and have almost no use for.”

Most of Mr. Madison’s interests are typical for his generation. But he is by no means a millennial stereotype, though he does live with his parents. “You cannot put that in the article in case there are girls that read this,” he told me.

It was far from a trivial pursuit, however. Just seven years ago, at the age of 15, he published his first crossword in the Times after a summer spent interning for Will Shortz, the paper’s crossword editor, up in Pleasantville, N.Y. “I’d never had an intern that young before,” Mr. Shortz recalled in a phone conversation. “I was a little concerned, actually. How could a 15-year-old know enough to be a good crossword editor?”

“I don’t know why he trusted me,” Mr. Madison recalled. “Maybe it’s because of my kind eyes.” Mr. Madison, who dabbles in stand-up comedy, is a jokester through and through, which makes his crosswords particularly rambunctious. While at Yale, he was the director of an improv group, the Viola Question, and published an Onion-style newspaper. In the first five minutes of our meeting, we peed beside each other in the bathroom near BuzzFeed’s kitchen area, which was sort of accidental, but also kind of awkward. He didn’t seem to mind. “Should we start the interview now?” he asked, dryly, from the adjacent urinal. “My stream says a lot about me.”

“In this field, you tend to run into people who are monomaniacs and have no personalities and no interests,” said the lexicographer Jesse Sheidlower, for whom Mr. Madison interned at the Oxford English Dictionary while in college. “But that’s not the case at all with him—he’s a very social guy.”

Most of Mr. Madison’s interests are typical for his generation—as evidenced by that book-themed crossword—but he is by no means a millennial stereotype, though he does live with his parents. (“You cannot put that in the article in case there are girls that read this,” he told me.) A sample BuzzFeed crossword recently contained a slew of clues—pop culture allusions, digital slang terms, Latin and Greek references—that convey Mr. Madison’s young yet ecumenical sensibility. (Example: “Like Four Brothers, which I know because I snuck into it at age 12.” Answer: “RATEDR.”)

As an undergrad, he immersed himself in media theory and semiotics, reading the works of Baudrillard, Chomsky and McLuhan. “To quote Liam Neeson,” Mr. Madison said of his disparate interests, “I have a very particular set of skills.”

Mr. Madison’s most formative influence was Ben Tausig, whose subscription-based puzzle, American Values Crossword—once published in the A.V. Club but now on its own—is an indie favorite, featuring a revolving cast of idiosyncratic constructors week to week. Mr. Madison was a constructor for Mr. Tausig—a kind of Hunter S. Thompson of the crossword world—and it’s Mr. Tausig’s voice, he told me, that he’s trying to channel at BuzzFeed. Mr. Tausig’s crosswords are conversational, often clued in the first person and include sexual, as well as scatological references. “It’s all with the aim of being funny as opposed to being controversial for its own sake,” Mr. Tausig told me. A recent puzzle by Aimee Lucido, for instance, was themed around breasts.

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It may be hard to see how revolutionary Ms. Lucido’s theme is if you aren’t familiar with the 100-year history of crosswords. The first was published by Arthur Wynne, a British-born puzzle maker, in the December 21, 1913 edition of the New York World. It was dry and loaded with synonyms, and it set the tone for the crossword as a kind of test of one’s intelligence—as manifested, later in the century, by Eugene Maleska, who took over the Times crossword in the late 1970s. Maleska, a former Bronx school superintendent, saw wordplay as a frivolous distraction. The object of his puzzles was didactic, to test the solver’s knowledge of arcane things like plant genuses, capital cities and etymologies—the kind of crosswordese that constructors cringe at today.

So when Will Shortz, Merl Reagle, Mike Shenk and other young turks came along in the 1980s and started publishing puzzles that included brand names and pop-culture references in Games magazine—a sort of Spy of the puzzle world—it was seen as a direct rebuke of Maleska’s stodginess. Things got tense. “The dispute is exemplified by the ‘oreo war,’ ” reported a 1988 Times article (titled “Puzzle Makers Exchange Cross Words”). “Old school constructors insist that if the puzzle demands the four letters o-r-e-o, then the clue should be ‘mountain: prefix,’ as in ‘oreortyx,’ or mountain quail. The new wave believes that if ‘Oreo’ is the answer, ‘cookie’ should be the clue.”

But history tends to repeat itself, and now the practices of Mr. Shortz, who took over the Times crossword in 1993, have ossified a bit, according to the indie puzzlers. Mr. Shortz and his cohort are, of course, appealing to a certain audience—Stan Newman’s mind-numbingly simple Newsday puzzle is a far cry from the adventurous stuff he published, samizdat-style, in his early-’80s newsletter—but the new wave of puzzle makers feel they have a fresh language to convey, eschewing easy fill-words like “OLEO” and “ASTA,” replacing them with answers that reflect the modern vernacular, like “SMH.”

Mr. Madison may encounter some resistance when he brings that vernacular to BuzzFeed, much in the way Games did 30 years ago. One constructor dismissed the forthcoming puzzle as too snarky for his taste. But Mr. Madison is well aware of the stakes. As much as he likes witty banter, he is also fascinated with how crosswords are perceived.

“The crossword as a medium is very, very slippery to talk about,” Mr. Madison said, “because I don’t know what interaction is even happening between people. It’s not like a movie or a TV show or a book, where you’re presenting another reality or a set of circumstances or a story. It’s more like a poem, where it’s a repurposing of words that are used to communicate to a different end.”

“Don’t tell that to any poets,” he added.

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With BuzzFeed, Mr. Madison will have the opportunity to expand the crossword’s limits beyond the realm of risqué answers. The nimbleness of digital allows for longer clues, for instance, since there are no space constraints. Each puzzle will get progressively harder as the week goes by, just like the Times, but they may sometimes be bigger than the typical 15-by-15 grid. He will be publishing, initially, from Monday to Friday but hopes to expand to Saturday and Sunday, too, if the crosswords get enough eyeballs. (He will also pay constructors $300 per puzzle, a rate commensurate with the Times.)

As a teaser, Mr. Madison has been making mini quizzes of weird shapes and sizes. He’s calling them “freestyles,” and he hopes they’ll attract solvers to the larger puzzles. Mr. Shepherd, the BuzzTeam editor who oversees Mr. Madison’s endeavors, is hoping his young charge will experiment as much as possible. Perhaps, Mr. Shepherd said, there will be puzzles with emoji clues, or breaking news crosswords based on current events. “The Internet has its own language,” he said, “and that’s something I think we can really tap into.”

Back in the BuzzTeam conference room, Mr. Madison was focusing on the top left corner of his Hunger GamesHarry Potter puzzle, which was still decidedly un-holographic. “I put in ‘JEREMIH’ first, and that gave me ‘EMOJI,’ which I like,” he told me. There were still about 10 more clues to fill in, depending on how you counted, but Mr. Madison seemed confident that he’d get through that part quickly enough, so he moved on to a different section on the other side of the puzzle grid.

“‘RAGNAROK’ is kind of fun,” he said after a moment, writing it in as he spoke. “I feel like it’s a Lord of the Rings thing, right?” I shrugged. “Let me double check.” He clicked out of the puzzle and Googled it. “Oh, it’s a Norse mythology thing. Never mind. I must know it from the Thor movies or something.”

Pause.

“Whoa! O.K., ‘ENABLER,’ ” he said excitedly. “That’s kind of cool, that’s like, current, but it gives me ‘UNAIS,’ which I don’t know, so I’m not going to put it in the puzzle.” He deleted the suspect word and mulled over some other possibilities, his fingers fluttering above the keyboard.

Later that day, I drew up an online dictionary and looked up “unais.” As it turns out, it’s the plural version of “unai,” a relatively uncommon term for the two-toed sloth.

BuzzFeed Is Revolutionizing the Crossword Puzzle