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

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."