The Genius of the Wise and Cranky Kaplan Twitter Feeds. 

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Nov. 30 2013 11:50 AM

Trench Coat, Unlit Cigar

The genius of the Wise and Cranky Kaplan Twitter feeds. Plus: Their authors, revealed.

Illustration by Robert Neubecker. Click image to expand.

Legendary New York Observer editor Peter Kaplan has died of cancer, according to the New York Times, at age 59. In 2010, Nathan Heller wrote about the Twitter feeds Wise Kaplan and Cranky Kaplan, which are written by two former Observer staffers as a "semi-private" joke in homage to Kaplan. The article is reprinted below. 

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Beyond the known forces conspiring to make a pigeon of an honest editor these days—the bottom line, the top brass, slide shows of dogs, Rupert Murdoch —there is, lately, the added fear that when you say peculiar things to writers, they will put you on the Internet. For several months, the close-knit, screen-dazed world of New York journalism has been caught up in the thrall of Wise and Cranky Kaplan, a Jekyll-and-Hyde pair of Twitter personae whose 140-character dispatches imagine Peter Kaplan, who edited the New York Observer from the mid-'90s until 2009, in a range of weird and waggish situations. The two feeds are co-written anonymously by former Observer staffers Peter Stevenson and Jim Windolf, and although their semi-private joke has lately started going public—the Village Voice not long ago alluded playfully to Wise and Cranky; New York Magazine's "approval matrix" dubbed the latter "brilliant" and "lowbrow"—the two accounts are still essentially undiscovered. They shouldn't be. Whether one has a table at Elaine's or a stool in the local dive bar (or both), the Kaplan dispatches offer one of the most entertaining and ambitious uses of Twitter yet.

Stevenson (who was the Observer's executive editor until last year) and Windolf (now a writer at Vanity Fair) say that they started the Kaplan feeds to keep each other entertained. Peter Kaplan is known to New York's newspaper readers as the man behind a jaunty, impudent voice that shaped the Observer through the flush years of the late '90s and on. Stevenson and Windolf, though, knew him as a boss, mentor, and eccentric. The Twitter parodies were meant to be an inside joke. Yet through their online comedy act, the journalists have nudged Twitter in a new, more literary direction. Unlike contrived and headache-inducing concepts like the "Twitter novel" or the serialized essay—long forms awkwardly broken into 140-character bits—the Kaplan narratives are colorful, varied, and fully wedded to the medium.

Wise and Cranky are the children of a lost New York. From breakfast until deep into the night, they travel back and forth between the city and the bedroom community of Larchmont, N.Y., charting a path among Manhattan's decaying cultural landmarks and greasy-spoon diners. Their heroes are the ghosts of jazz greats, long-dead stylists, and midcentury entertainers. In another time, Wise Kaplan and his démodé tastes might have found a home in the pages of a dime novel: The character is self-possessed but chronically bemused, the sort of guy who has just re-emerged into the world after decades in his own head. Stevenson and Windolf describe him as "all anxiety." A few weeks back, a tweet found Wise camped in his car like the hero of a noir flick:

Outside secretary's modest house in Yonkers. Rain on Buick windshield. Small bourbon, small binoculars. Dance for me, you splendid lady.

This is Wise Kaplan in a nutshell: wistful in temper, anachronistic in style, and seedily transgressive in pursuits. (Stevenson considers Wise the "more dangerous" Kaplan of the pair because he has the softer purr.) But the central pleasure of this tweet is verbal. The sentences above have a lovely, faux-poetic economy at odds with the creepy encounter they describe. To conjure such a character and moment in just 136 characters, and with oblique humor and allusive style to boot, calls for a deftness that is rare in Web 2.0 prose. The best Wise Kaplan tweets are occasionally the most precise writing I read all week.

What Cranky Kaplan lacks in precision, he makes up for in his appetites. Cranky is everything that Wise is not: noisy, lewd, and full of rage. Windolf describes him as the Id incarnate, but he's more like the Id at the peak of an uppers binge. Writing in all-caps all the time, he zooms through town on his Segway scooter, guzzling gin by the pitcherful. His exuberance is the Van Damme version of Wise's Woody Allen pleasures. "SEGWAY PURRING LIKE GOD MADE HER AS WE RIDE UP TACONIC, DEVIL ON OUR TAIL GIN ON OUR AGENDA, CARRY ME HOME YOU FUCKING PIECE OF SPACE JUNK," he exclaimed one summer night. Cranky's special high jinks are full-frontal sorties on the literary world. He likes to target Ayelet Waldman, a novelist and columnist who's married to Michael Chabon ("MR PROSE STYLE"), with lurid propositions. Lately, his lubricious drives have slouched toward Susan Orlean. (She replies in kind.) When Cranky isn't randy, he is hostile, and his favorite bull's-eye in the industry is Michael Wolff, Vanity Fair's media columnist and the founder of Newser. Mostly, though, Cranky just raises hell. A typical tweet:

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