E. B. White's "Here is New York" has followed me around now for almost 25 years. I was given a copy of White's essay on my first trip to New York City, when I was a teenager, and I zoomed through it on the car ride down. It's not surprising that my 24-hour tour of the usual tourist spots (the United Nations headquarters, the Empire State Building -- where I got stuck in an elevator descending from the observation deck, I swear to God) didn't jibe with anything I read in White's book. And I'd forgotten about the book until this summer, when I found myself making the move I swore I'd never make: leaving Boston, where I'd lived all my life, to move to New York. Browsing through a bookstore in my new neighborhood, I came across White's book, which has just been republished in a 50th anniversary edition with an introductory appreciation by Roger Angell.

Some background: White was originally commissioned (by Angell, his stepson) to write the piece for Holiday magazine in the sweltering summer of 1949. By then, White had left New York for his home in Maine. In his foreword to the new edition, Angell notes that while the book now calls up nostalgia for post-war Manhattan, White had put his own nostalgia for the New York of his youth into the essay.

There's no denying the appeal of "Here is New York." To most of America, New York City embodies both romantic dream and urban nightmare, the place where we expect to find Fred Astaire taking to the floor in some Art Deco nightclub and a sap-wielding mugger waiting around every corner. White ameliorates those fears and substitutes the more realistic pleasures the city offers. Here is the threatening metropolis broken into small, self-contained neighborhoods; the immense city recast as a way to both lose yourself and find yourself; the embarrassment and out-of-place misery of tourists that results in charming faux pas; the most tender flower of young love blooming at a summer evening band concert. Anyone who wants to see New York but feels timid about actually braving it would read White and feel encouraged. And if you've moved to New York and are trying to feel your way into the city, you may take comfort in White's portrait of it as a place both open to the point of rawness and peculiarly insulated. At times White seems like the wise older uncle giving a blunt but not discouraging pep talk.

It's also possible, I think, never to have set foot in New York City and still recognize that "Here is New York" is almost completely phony. Certainly it's possible for outsiders to write intelligently about a place (isn't that what travel writing is all about?). But even a detached observer must be willing to engage with his subject if his observations are going to have any degree of authenticity. White doesn't. "Here is New York" is the work of a man who had decided long before he took the assignment that New York no longer held anything for him. That's discernible less in the sections where White laments the passing of the New York he knew (measuring its loss in newspapers that have folded, cops forsaking their beat for patrol cars, projects replacing slums, cabs replacing hackneys) than in the clichis he reverts to in order to describe what he sees. "A poem compresses much in a small space and adds music, thus heightening its meaning. The city is like poetry: it compresses all life, all races and breeds, and adds music and the accompaniment of internal engines." Is there a freshman composition teacher anywhere who wouldn't have at that trite metaphor like a bull sighting a red flag?

In a dissenting 1947 opinion on White's much-revered essays, critic Robert Warshow wrote of White and the New Yorker that they "always dealt with experience not by trying to understand it but by prescribing the attitude to be adopted toward it. This makes it possible to feel intelligent without thinking, and it is a way of making everything tolerable, for the assumption of a suitable attitude toward experience can give one the illusion of having dealt with it adequately."

Thus, White can encounter the residents of the Lower East Side sitting on their stoops on a hot summer night and banish the crowding and poverty by transforming it into "the nightly garden party of the Lower East Side ... It is folksy [emphasis added] here with the smell of warm flesh and squashed fruit and fly-bitten filth in the gutter, and cooking." Visit exotic New York! See the quaint and colorful peasants! "A large, cheerful Negro" panhandler begging coins from a crowd exiting a Broadway show prompts White to observe that "a few minutes of minstrelsy improves the condition of one Negro by about eight dollars. If he does as well as this at every performance, he has a living right there." (And eventually, no doubt, a summer place in the Hamptons.)

Imagining the budding artists drawn to New York, White sustains a patch of hokum better suited to one of Carol Burnett's parodies of '40s movies: "Whether it is a farmer arriving from Italy to set up a small grocery store in a slum, or a young girl arriving from Mississippi to escape the indignity of being observed by her neighbors, or a boy arriving from the Corn Belt with a manuscript in his suitcase and a pain in his heart, it makes no difference: each embraces New York with the intense excitement of first love, each absorbs New York with the fresh eyes of an adventurer, each generates heat and light to dwarf the Consolidated Edison Company." Even allowing for a distance of 50 years, did this ever sound like anything more than a load of hooey? Is there anything in White's thumbnail caricatures of the folksy poor, the cheerful Negro, the disgraced girl or the anguished young writer that he couldn't have gotten from the bottom half of a double bill or by scanning the paperback rack in his hotel newsstand? He solves the problem Warshow noted, the messiness of actually confronting experience, by substituting clichis out of radio melodrama, B movies and "women's" fiction.

Throughout the essay, it's White's language -- once praised by William Shawn as "thoroughly American and utterly beautiful" -- that continually gives him away. It doesn't hit the excruciating depths of Richard Nixon trying to sound like a regular guy by asking David Frost, "How was your weekend? Did you do any fornicating?" But its false bonhomie is that of a man deeply uncomfortable with the quickness and slanginess and good-natured rude energy of American vernacular, a vernacular that reaches its apex in New York City. Warshow quoted White as saying, "Allied soldiers had a hunch that they disliked the idea behind the word 'Heil.' They preferred the word 'Hi' -- it was shorter and cleaner." Apart from the insulting notion that Allied soldiers were so simple and goodhearted that they fought and died over a syllable, the whole tone of that sentence feels as off as a Mentos ad. Can anyone imagine the man who wrote it saying, "Hi!" like he meant it, as if it came naturally to him?

New York magazine once ran a competition in which readers were invited to submit titles that just didn't make it. Some of the winners were gems like "The Sun Comes Up Too," "The Colored Gentleman of the Narcissus" and "Those Karamazov Boys!" Reading "Here is New York," it struck me that all the entries could have been penned by E.B. White. His phrasing has the feel of someone trying to pass himself off as an average, casual man by trotting out old chestnuts and awkward locutions: "By rights New York should have destroyed itself long ago ... It should have been touched in the head by the August heat and gone off its rocker." On hailing a cab: "You grab a handle and open the door, and find that some citizen is entering from the other side." Citizen? Not fellow, or guy or even schmo? And White's pretensions to plain-spokenness just wind up making his grandiloquent moments sound even worse: "In Turtle Bay there is an old willow tree that presides over an interior garden. It is a battered tree, long suffering and much climbed, held together by strands of wire but beloved of those who know it. In a way it symbolizes the city: life under difficulties, growth against odds, sap-rise in the midst of concrete, and the steady reaching for the sun." And, Honey, I miss you. And I'm being good.

White's insulation from everyday life isn't just the main characteristic of his writing about New York -- I'm guessing it's the reason for this essay's continued appeal. In his foreword, Angell says "If Andy White could visit New York once again ... I think he would want to rush back home to Maine the same afternoon." Angell goes on to list the usual suspects: crime and violence (without noting that they are at record lows), increased rudeness and diminished sophistication, evidenced by people who dress entirely in black. (And why not? It goes with everything, resists showing dirt and is slimming besides.) But "Here is New York" makes it clear that White had the same impulse to high-tail it Down East even back in the summer of 1949. I question how truthfully anyone can write about New York while disdaining its common energy and dirt (or at least making those qualities the basis for an honest account of revulsion). We should expect more from a writer who has taken it upon himself to engage with the city. White spends paragraphs insulting the commuters who, he says, see only the train station and the block of their office building before retreating to the suburbs. But those are precisely the people that "Here is New York" is written for. It contains about as much authentic experience as a theater weekend.

Luckily, we don't have to be satisfied with "Here is New York." The last few years have seen the reprinting of some particularly evocative New York writing that captures the tone of the city between the '40s and the early '60s. There is Joseph Mitchell's "Up in the Old Hotel," the fruit of a lifetime's wanderings; the glimpses of the moneyed classes in the novels of W.M. Spackman; the chill creeping through postwar New York in the three novels that make up Isabel Bolton's "New York Trilogy," novels that suggest an American Jean Rhys. Recently there was the genuine curiosity and compassion of the vignettes in "Keys to the City," Joel Kostman's account of the people he encounters as a New York City locksmith. Best of all, there are Maeve Brennan's New Yorker Talk of the Town pieces collected in "The Long-Winded Lady" (the name she signed to those pieces).

It may seem odd to make a case for writers being engaged in their subject by pointing to a writer who was so much of a loner. The impression you take from reading Brennan is of someone more comfortable with the temporary, demarcated relations she had with waiters and bartenders and shopkeepers than with the potentially messy interactions between friends and lovers. And yet the rootlessness that seems to be Brennan's permanent condition, the sidelong judgments that have a way of sticking with you (seeing Park Avenue after reading Brennan's description of it, I realized she was right: take away the trees and it would be the most anonymous avenue in the city), her constant alertness for whoever ventures into her sphere and her dedication to rendering them as exactly as she can are all the signs of someone willing to encounter New York, even if she rarely ventures outside the role of silent observer. Her book's best piece, "Faraway Places Near Here," ends with her encounter with a familiar panhandler whom she approaches to assuage her guilt over lunching in a good restaurant, only to see him riffling through the back seat of a parked car. Where White might have said, "Ten cars like this a day and the fellow would have found a living," Brennan is afflicted by a mixture of guilt and shame and confusion that "no hail fellow, well met" remark will clear away.

It's the combination of being willing to be open to the unexpected and resisting the temptation to see the city in CinemaScope that provides the truest New York writing. Being true to the specific oddities or generosities or cruelties she encounters keeps Brennan from falling into the shallow knowingness of White's attempted overview. Even just a few months in New York is enough time to begin noticing your own oddities. I like the way you can guess at the makeup of a neighborhood by seeing what porn mags are featured on the newsstand (in my neighborhood, it's "Black Tail"). I like the way that dogs seem to act as the city's goodwill ambassadors, expressing the enthusiasm and friendliness their owners keep bottled up. I like gawking at the length of subway cars, which makes me feel just as much of a hick as gawking at tall buildings but is a lot less obvious. I hate that there are no baggers in my local supermarket. I'm not yet comfortable with white eggs. I hate watching the cops roust black kids drumming and dancing in Times Square station but not bothering the white classical musician who takes the dancers' place. I hate Times Square. Nothing depresses me faster or more reliably than seeing the tourists who've flocked there and who are trying to convince themselves that they're having a good time. The most amazing thing about New York City to me is that I'm actually enjoying myself here. That was the most unexpected event of all, but I'm getting used to it.