Trench Coat, Unlit Cigar

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

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. 

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:


Cranky has more than twice as many followers as Wise, and his vulgar, shouty act probably accounts in large part for that figure. (Stevenson says, “The Cranky Kaplan retweets, aside from being from Spanish people”—a phenomenon he and Windolf have yet to figure out—“are from frat kind of guys.”) But although Cranky’s dirty bombs are crass, they’re not crude. The modest example above offers a surprise at each turn: Its opening, Cary Grant-esque nicety is made absurd by the livid all-caps. Just when we expect to get more social graces, Cranky’s “nuts” drop into play. They aren’t a statement of machismo, though—the nuts make clinky machine noises. We end with a bizarre, Observer-style pun.

These constant turns away from expectation would be funny on their own, and they are doubly so when spoken by a crazed, middle-aged editor on a scooter. But it’s Cranky’s breakneck parody of tired forms—the cocktail badinage, the locker-room braggadocio—that gives the verbal gag its comic teeth. Cranky Kaplan maybe the only scrotal rhapsodist with the mental reservoir of a cultural critic.

Several people, including Stevenson and Windolf, have likened the Kaplan Twitter accounts to a comic strip. It is a reasonable comparison. To follow Wise and Cranky is to learn the landmarks of their outré world. You come to know the characters: Fat Billy the Fact Checker, Cryptic Managing Editor, Oddly Lanky Summer Intern, Mildly Retarded Cousin Jeremy, Cranky’s raccoon nemesis, and many New Style Girls—the twentysomething liberal-arts and publishing-world types whose taste, attire, and sense of humor the Kaplans find totally inscrutable. You know its tropes: for Wise, the anxious ™-ing of every common phrase, the hoary exclamations (“Whatta town!”); for Cranky, the tweets that end with a gratuitous fuck you. The question, for a reader of the Kaplan feeds, is how these two fully formed fictionalized characters came to flourish in a medium normally reserved for homespun aphorism, random links, and dispatches from the line at the drugstore.

Not long ago, I met Stevenson and Windolf at the Grand Central Oyster Bar, a cavernous tile-clad restaurant nested beneath the train station’s main level, at the foot of the Larchmont line. Stevenson has a solid bearing, dark-brown hair combed back behind his ears, and thick-rimmed glasses. With loose jeans and an old leather bag on one shoulder, he looks like somebody a casting director might recruit to play a fortysomething journalist; in conversation, he has the comfortable, amused manner of a guy who’s just leaned back to take a phone call from a friend. Windolf, meanwhile, seems fixed to the edge of his seat. Wiry, with a close-trimmed poof of hair the color of a charcoal suit, he speaks in rapid-fire sentences that slow to clinch a joke or to underscore a passing irony. When something strikes him as funny, which it often does, he lets out a breathy, clattering giggle, like a pot of pasta boiling over its lid.

Stevenson and Windolf started the Kaplan accounts seven months ago as a kind of perverse tribute to their early-career mentor. Stevenson created Cranky; Windolf started Wise; within a few days, they’d swapped passwords and begun to author the two feeds together. The Jekyll-and-Hyde split was meant to be a satirical parsing of Kaplan’s enigmatic personality. Wise’s quirks are based in the editor’s tastes and habits—his gray-flannel-suit commute, his “boyish enthusiasm” for New York, his love for Liza Minnelli, his outsize flâneurism. (Stevenson said, “Peter Kaplan has this natural ebullience on the street. Like, if he sees a model walk by, he’ll stop and turn around and put his glasses down. He’ll do one of these”—Stevenson took his own glasses from the table, where they lay folded, draped them on the end of his nose, and whirled around to face an imaginary beauty—” ’Holy moley!’ “) Cranky is a comic reimagining of Kaplan’s inner life. “There is something about him,” Stevenson said, “that does have a coiled rage.”

The Wise and Cranky project clicked into focus on New Year’s Day, when Cranky’s DirecTV dish blew off his roof and landed in a Koi pond and Stevenson and Windolf realized that the Twitter form could carry little plot lines. Since then, they’ve been adding twists and turns to the feeds in the spirit of a free-form relay. They never schedule shifts, they say, or talk offline to plan ahead. (A third account, Real Kaplan, rattled to life yesterday and is just starting to find its comic voice.)

Together, Wise and Cranky bridge the gap between Twitter’s wry and hashed-up rhythms and an older, all-but-lost style of comic storytelling. Neither Stevenson nor Windolf is a member of the Twitter generation. Both are in their 40s now. They came to the Observer as young men in the early ‘90s, before Kaplan, and they honed their craft in an era when newsprint was king. The Observer is famously a writer’s paper, but it was also Johnny on the spot for boom-era New York: a newspaper born out of the lore of newspapers, reporting on a city that was likewise rebuilding itself on the groundwork of its own mythology. Although Stevenson and Windolf have both moved on, the Kaplan years linger at the core of their vocational identity. Stevenson said, “The fun of these Twitters, in our mind, is the continuation of the voice of the New York Observer that we loved.”

He and Windolf first got practice writing in a shared voice in the ‘90s, playing pranks on Peter Kaplan and the rest of the Observer staff. They played a lot. Swapping drafts back and forth, they’d forge memos from Kaplan, imparting the details of a lackluster Christmas party or a staff retreat at the Ramada Inn. They drew up phony issues of the paper parodying the prose style of writers who were on their way out. And they composed bitter, bawdy roasts for Kaplan’s birthday dinners at Elaine’s. Not all of their jokes were verbal: Once, they took the automatic spray deodorizers off the wall of the men’s room and hid them in Kaplan’s office, where they’d dispense during meetings.

Shortly after meeting with Stevenson and Windolf, I got a call from Peter Kaplan, who is today creative director at Condé Nast Traveler. In a previous e-mail, Kaplan had described the Wise and Cranky portraits of him, which his children follow, as “extraordinarily accurate.” I was interested to learn how far he thought the similarities went.

Real Kaplan does not participate in Twitter, and seemed alarmed by the idea of trying, but he said he checks the Wise and Cranky feeds every couple of weeks and believes the characters capture something real about his inner life. “I said to somebody at the beginning, it’s a little bit like being Jack Benny,” he said. “You have this staff writing you. It’s somewhat like you. It’s truer emotionally, obviously, than literally. Both those guys, Wise and Cranky, are some weird combination of irrational and somewhat sentimental.” Kaplan lifted his voice half a register and gave a plaintive sigh into the blower. “I mean, for me, it’s a big, beautiful narrative poem,” he said. “It’s this incredible ongoing haiku.”

Kaplan told me that he feels greater affinity with Wise than with Cranky (“I’ve never gone near gin in my life. It’s bad stuff. You shouldn’t drink it, either, Nathan”) but that he’s pleased to be in the tank with both personae. “Listen, I’m your basic squeamish guy. I’m not crazy about anything involving bodily functions. But that aside, nothing’s really made me uncomfortable,” he said. “I don’t go to many parties, but every once in a while, at a party, somebody will tell me how great my tweets are, and I always thank them. I never disabuse anybody, because—why would you, you know? It would be like telling them you weren’t Ring Lardner.”

Stevenson says that when he meets Real Kaplan these days, he sometimes catches himself taking mental notes, filing away turns of phrase that may someday be fodder for the Twitter characters. “As much as it’s an idiotic hobby,” he explained, “we actually work on it.” He and Windolf say they each spend a total of about an hour a week writing for the accounts. Windolf: “We’re probably underestimating so we don’t look too bad.”

Although the Kaplan feeds have good days, bad days, and vulnerabilities—the tone and plot lines of the Wise and Cranky accounts have slowly been converging—the Kaplans have so far enjoyed nine lives both in creative stamina and in their fictional world. Cranky was once run down by a Volkswagen. Wise, not long ago, leapt from his office window. His dive, a lovely free fall down the Condé Nast building, defied physics, played off Twitter’s frame-by-frame short form, and perfectly distilled the Kaplans’ resilience to the perils of their madcap world:

Not even Jack Benny could hit that mark.

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