The making of a brand-new iPad magazine that’s already sick of the Internet

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Jim Windolf and David Bennahum. ()
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Jim Windolf, a contributing editor and writer for Vanity Fair, was sitting in a large, multi-desk cubicle in a warren of similar cubicles in a 10th floor office on West 27th Street on a rainy afternoon, explaining his new project.

The office, a temporary space shared with a bunch of local startups and paid for by the desk, was spare, but what stood out were the stacks of books, and a big copy of the Spy magazine anthology that came out in 2006. It was his sixth day on the job, and he made several apologies for having not much specific to say about his plans. But he actually had a lot to say.

Windolf, 48, is a recent addition to the group of people who are behind Punch!, a new iPad publication that is, for now, mostly a sparsely populated "bookshelf" of interactive games and visuals and other little graphic toys on the broad themes of contemporary politics and pop culture news. (It's free at the App Store, here.)

"The web is increasingly feeling like noise and bother," he said. "I mean I read it, all day. But I don't always feel so good afterward." 

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What he sees in Punch! is the possibility of creating a successor to Spy, the seminal late-'80s monthly-magazine brainchild of Kurt Andersen and Graydon Carter that was a turning point in the culture of magazine-making and reading. It was a relatively short-lived, money-losing proposition that, in the final stages of its growth, scattered its seed across Manhattan like some kind of plucked dandelion, sprouting nasty bits of yellow everywhere it landed.

"On the other hand, I used to read Spy and not feel great afterward, either," he said. "That's something people forget."

The two of us had thumbed through the Spy anthology and he had been pointing admiringly to lots of its pieces and features. We both found ourselves doing what one always does looking at that book: Wondering where the energy came from to be so enervated about the culture, to have it sprout out so easily, so messily and so perfectly on the page. 

Windolf, a former editor at the Spy-inflected New York Observer (where I also worked, though not at the same time) wasn't really contradicting himself about that feeling of indigestion. 

Much of the web is an endless array of little bites one after the other, a Tapas restaurant from hell. At some point you walk away from the table and pay an astronomical bill, but those little bites are still arriving at other tables, piling up in your absence, swimming in garlic and grease. It's possible that nothing you've tasted yet is as important or as good as the things now accumulating there, you think, as you make the difficult choice to walk away.

Spy was something else: A big, rich meal, served at a white tablecloth, course after course. Before long, dawdling over each plate becomes something you do in the hopes that someone will take it away, and that suddenly you'll be given a cup of coffee, or some other sign that your gluttony was near an end. And then you got it: the last page of the magazine. You wouldn't be eating again that way for a month.

Windolf pointed to a piece by Philip Weiss that appeared in the November, 1989 issue of Spy, called "Masters of the Universe Go to Camp: Inside the Bohemian Grove."

The piece clocks in at 10,000 words—hardly the stuff to down between courses of data entry or legal briefs or stock trades. But it is also spread out in the magazine over 13 pages, giving each page a very luxurious average for cartoons, photos, and sidebars.

"Spy always seemed like it was fighting the limits of what you could do with print," Windolf said. 

There are lots of reasons publishers of magazines, long-form journalism and nonfiction writing and the like have hailed the coming of the iPad. The boring part of all that is whether the simple fact of the new platform allows publishers a pretense to start charging for content. The interesting part is what happens when publishers, many of whom have for some reason or another never really taken the time to develop a language for their literary ambitions on the Internet, actually begin doing so for the iPad.

Windolf brought up the early Soviet film director and theorist Sergei Eisenstein.

"In early film, someone had to invent the grammar of it," he said. "That you have a shot of someone looking to the right, and then cut to someone looking to the left, that they are looking at each other—that was invented. They had to invent the grammar of film."

Publishers' work on the internet pales in comparison, really, to those 20 years at the beginning of film when it comes to developing a web-specific storytelling grammar. And that's where Windolf, like some others before him, sees some potential.

"It's specific to the tablet, to swiping around and moving on the surface of something rather than clicking and typing," he said. 

So far, there isn't much on Punch! that could really exist anywhere else. 

There's Cabin Pressure, an illustration featuring a cutaway model of an airport with a plane on the nearby tarmac that comes with the sound effects of a muted airport P.A. system. You quickly gather that touching various people and things around the airport will bring up a box with a little story in it, like, say, one that makes reference pop singer Bjork's history of getting into trouble at airports.  Some items have video or pictures in the box that you can touch to watch. You certainly could make this for the real internet, and have hover-states for the mouse pointer that told you where to interact. But in all likelihood nobody would, because the economy of the internet provides a strong disincentive to spend the money and development time on something like this, which audiences will often reach unintentionally.