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:
9:05:26 p.m.: Standing on windowsill, telling secretary I'll jump if she leaves me now. She says I don't have the guts and the window doesn't even op
9:05:59 p.m.: Awning.
9:06:27 p.m.: Nother awning.
9:06:43 p.m.: Yellow Cab™ roof.
9:11:23 p.m.: Whatta town.