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Chapter One: Midtown South: Second Avenue

22nd Street to 28th Street

One day, while wheeling two-year-old daughter Tracy in her stroller, I made a startling discovery. A row of tenements on the north side of 26th Street close to Second Avenue had vanished. Absent the buildings, the Empire State Building, a ways away at Fifth Avenue and 34th Street, sprang up like a giant jack-in-the-box.

The two buildings adjacent to the demolition site—clearly next on the razing block—were unexpected wonders. Their tall, bracketed pediments rose high above the cornices, enclosing identical sculptures: long-haired Victorian-looking ladies with sweet faces, wide wing spans, and clawed feet gripping balls. The wrecking crew, although mystified by the request, agreed to save the eagle ladies for me. The laborers warned me, however, that the brownstone sculptures would weigh a ton. They must have been surprised when the pieces turned out to be made of much lighter tin, for they inexplicably tossed the first one down into the rubble. Happily, the remaining sculpture made it safely to my apartment. Several dwellings later, she is still with me, soaring atop the double doorway between my living and dining rooms.

The newly created building site was filled in by 225 East 26th Street, a seven-story rental apartment house of 1963. The two tenements to the east (right) are still standing. I mislabeled my painting of the streetscape: the Eagle Lady was at 233 (not 235) East 26th Street.

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Chapter Two: Midtown South: Third Avenue

21st Street to 34th Street

In a view from 23rd Street northwest across Third Avenue, the wood water tower atop the tripartite George Washington Hotel seems to compete with the campanile of Met Life—but in vain. Although the rear of the hotel presents a blank face in this view, the front and side facades of the lower floors of the 1928 French Renaissance Revival–style hotel at 23rd and Lexington are heartbreakingly lovely. Clad in handsome salmon-colored terra cotta, the building has arched windows decorated with elaborately carved pilasters and winged putti. The once-esteemed hotel has hosted a brothel and, during Prohibition, a bootleg enterprise; in the 1930s, it was the lodging of choice for such creative types as writer Christopher Isherwood and poet W. H. Auden. After the hotel’s eventual decline, its architecturally significant features saved it from demolition. The building was subsequently leased to the School of Visual Arts for dormitory space, though a few fortunate early rent-stabilized tenants were able to remain. In 2016, SVA built new dorms on 24th Street and the property’s ground lease was purchased by the investment firm Alliance Bernstein, which remade the building as budget-conscious hotel Freehand New York.

To the east (right) of the 18-story hotel is the short but architecturally noteworthy Madison Square Station post office of 1937; it is almost indecipherable in the painting. Designed by Lorimer Rich, the Classical Revival structure has a facade and Doric piers of polished Dakota granite. Its street front bears bronze plaques with witty relief sculptures that represent different forms of communication: the god Mercury, jungle drums, mail, carrier pigeon, and smoke signals. The building is on the U.S. Register of Historic Places.

Beneath the two water towers in the center of the scene are four brick tenements in a block-long row. By 2006, a blindingly white, 21-story brick-and-glass building had assaulted the wide sky, forever obliterating from there the sight of the glorious New York Life Tower. The New York University dormitory devoured the entire row of tenements except for the one on the 24th Street corner, making this part of the neighborhood feel like a college town.

At the southeast corner of 23rd and Third (just out of view to the left) was Connelly’s, an esteemed watering hole that served the area from 1925 to 1975. County Sligo–born Tom Connelly ran the saloon until his death in 1937, when his son Gene, an MIT-trained electrical engineer, took over the business. The highly polished exterior was faced in bronze, with five sets of beveled glass doors and large windows topped with stained-glass panels. Below its pressed-tin ceiling were walls and booths of mahogany; the long marble-topped lunch counter had a brass foot rail. On Mondays, smoked pork tenderloin was served; Wednesdays brought Irish lamb stew. At its closing, a Connelly’s partner commented, “I’d say it’s been the home of good fellowship.” The site has since been occupied by a bank, a bodega, and other local businesses.

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Chapter Three: Midtown: Third Avenue

40th Street to 60th Street

The stark contrast between old and new along the east side of Third Avenue suggested, to me, a “tenement sandwich.” The ragtag walk-ups between 52nd and 54th Streets are the filling; the 1960s office towers surrounding them are the bread.

The southern slice (right) is 845 Third Avenue, a block-long office building between 51st and 52nd Streets. Designed by Emery Roth & Sons, the 21-story International Style structure was built in 1963. The American and British flags in front indicate two of the tenants: the U.S. Passport Office (since relocated) and the British Consulate General.

The northern slice is another full-block building, 909 Third Avenue of 1968, between 54th and 55th Streets. Max O. Urbahn Associates and Emery Roth & Sons (again) designed the brutalist tower. The FDR Station Post Office occupies its podium base. The AIA Guide to New York writes: “The tower’s deeply coffered, cast concrete walls seem a honeycomb for the killer bees of Manhattan businesses.” One block to the north stands the (tall for the time) 47-story 919 Third Avenue, designed by Skidmore, Owings & Merrill. P.J. Clarke’s survives on the 55th Street corner.

And what of the tenements in between? The 52nd–53rd Street block would become the site for 875 Third Avenue. Skidmore, Owings & Merrill designed the structure around the “holdout” tenements on the southeast corner. The 53rd–54th Street block would be demolished for 885 Third Avenue, Philip Johnson’s Lipstick Building. The bus in front of the tenements bears my snarky message “Stay Home.”

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Chapter Four: Midtown: Madison Avenue

48th Street to 60th Street

My reference photographs for this streetscape of Madison Avenue from 55th Street north were taken from across the street, near the New York Exchange for Woman’s Work with its red-and-white-striped awning (changed to green sometime before I documented it in 1980; plate 58). The Women’s Haberdashery shop, the low white building at the corner of 55th and Madison, is draped in sleek mid-1930s Moderne. Its windows, trios of short-tall-short, chase each other around the limestone facade. The building was a two-story taxpayer: many of these structures, built during the Great Depression, brought in just enough rent to cover the property taxes.

556 Madison Avenue, directly to the north (right) of Women’s Haberdashery, was once a private brownstone, as all the buildings on the block had been. By 1969, its lower two floors had been altered for society stationers Dempsey & Carroll. The company’s calling card of an advertisement is painted discreetly but colorfully on the building’s south wall. Next door is a seven-story limestone building with polished granite details and distinctive second-story oval window. William Van Alen, soon to design the Chrysler Building, reconfigured the row house in 1926. The Alice Maynard needlepoint shop occupied the first two floors. Christopher Gray once posited, in his Streetscapes column, that the broken pediment of number 556 might have influenced the broken pediment of the 37-story AT&T (then Sony) Building, which replaced it in 1984. The architect, Philip Johnson (with John Burgee), was not amused. Once humorously referred to as the “Chippendale building,” AT&T/Sony is now simply 550 Madison Avenue. Its distinctive exterior was landmarked in July 2018.

A sedate 12-story mansard-roofed apartment hotel, the Hotel Essex, occupied the northwest corner of Madison and 56th, sharing the block with a building for IBM. For many years, Henry Halper Chemists was resident in the ground floor of the Essex. It was known as much for the long soda fountain/lunch counter facing 56th Street as for the fashion models perched on the stools: the offices of Mademoiselle and Charm magazines were across the street. The rear of the pharmacy had a wide bank of wood-and-glass telephone booths, an unofficial Midtown basecamp for those needing to set up appointments. The stepped-back 22-story IBM building of 1926 was designed by Donn Barber and known as the Ley Building. The blockfront was replaced in 1983 by a new IBM tower designed by Edward Larrabee Barnes. Clad in polished gray-green granite with horizontal bands of tinted glass in the same color, the prismatic 41-story building has five sides and a perilous-looking cantilever suspended several floors above the 57th Street corner entrance.

In the distance to the northwest (upper left) is the white limestone Squibb Building of 1930, which occupies the southeast corner of 58th Street and Fifth Avenue. The backdrop to the entire scene is the 50-story GM Building; the high-rise is set back from Fifth Avenue by a plaza more than a hundred feet deep and otherwise takes up the block between Fifth and Madison and 59th and 60th. It was completed just one year before my painting was done and lords it over all the smaller animals in the urban barnyard.

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Chapter Five: Midtown West

Times Square To 57th Street

Painted wall advertisements started to appear throughout New York in the late 1880s. They were executed by artists who referred to themselves as “wall dogs.” Frank Jump documented many of the works in his book Fading Ads of New York City. Whispers of early signs are still to be found: produced with lead-based paint, owners feared the health hazards of sandblasting them off.

One such notice, a guest from the 19th century, takes center stage in my busy 1998 scene: an advertisement for J. A. Keal’s Carriage Manufactory. New York Times columnist David W. Dunlap reports that business directories from the 1870s showed Keal’s factories—“carriages, light wagons and phaetons a specialty”—at several addresses around Longacre (now Times) Square. This particular ad plugged the branch at 1515 Broadway, two blocks south (left) between 44th and 45 Streets. The billboard vanished behind new construction but reappeared fleetingly when the later structure was razed for the glitzy W New York—Times Square.

In 1904, the Keal’s branch on Broadway made way for the luxe Astor Hotel. The hotel, in turn, was replaced by the 54-story One Astor Plaza in 1972. The black glass tower, designed by Der Scutt of Kahn & Jacobs, stands at the south end of the streetscape; its top is adorned with pointed white projections (plate 66).

Large-scale painted advertisements succumbed to printed vinyl and, more recently, to digital displays that rotate through a series of messages. But two of the outmoded notices feature in my scene: the blue Maxwell House billboard (“Good to the Last Drop”) and the placard for Yasmina Reza’s play Art.

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Chapter Five: Midtown West

Times Square To 57th Street

The city once dispensed unexpected vistas with regularity: sudden glimpses over low-lying buildings opened up to distant high-rises like a folded fan opens up to a vividly painted scene. In this serendipitous outlook streetscape, low stables on 52nd Street frame two 59th Street towers.

Although in decline by 1983, 52nd Street between Fifth and Seventh Avenues reigned as Swing Street for the 50 years following the repeal of Prohibition. Clubs such as Jimmy Ryan’s and Leon & Eddie’s hosted jazz greats Thelonius Monk, Marian McPartland, and Billie Holiday. Glowing neon signs announced the eateries Hickory House, House of Chan, and Lum Fong’s. This scene documents Peking Paradise, Blarney Stone, and Bill Hong’s. All three tenant converted stables, though Bill Hong’s venue is disguised by a modern facade.

To the east (right) is the rear section of 1301 Avenue of the Americas of 1964, between 52nd and 53rd Streets, and the massive New York Hilton Midtown of 1963, between 53rd and 54th. These were two early efforts to transform tawdry Sixth Avenue into corporate Avenue of the Americas. The parking garage to the west (left) of the low stables is part of the Sheraton Centre (today the Sheraton New York Times Square). The hotel, designed by Morris Lapidus, retains its striking yellow-brick spandrels.

The former stables were replaced in 1985 by a 47-story commercial and residential structure, the Manhattan, designed by Rafael Viñoly. Financial difficulties left the building empty until 1991, when it became the Flatotel. By 2013, the wheel of fortune had turned once more. Today, floors 2 through 6 are occupied by commercial space, while the upper floors have become a glimmering residential condominium. Architect CetraRuddy inserted floor-to-ceiling windows, a 423-foot “light saber” installation by French lighting artist Thierry Dreyfus, and a soaring lobby.

The surprise view north from 52nd Street focuses on two Central Park (aka 59th Street) South buildings. Hampshire House, the 37-story white-brick apartment tower designed by Caughey & Evans, was completed in 1938. Its interiors were the work of America’s first interior decorator, Dorothy Draper, while the twin chimneys are reminiscent of those atop the splendid Savoy-Plaza Hotel (see plate 60). The 44-story Art Deco Essex House of 1930 was designed by Frank Grad as a residential hotel, and in 1979, it was redone as a condominium/luxury hotel combination. Today it is called JW Marriott Essex House. Still dear to the hearts of New Yorkers is the giant illuminated rooftop sign. How the city smiled, some years ago, when the first two letters of “Essex” burned out.

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Chapter Five: Midtown West

Times Square To 57th Street

The word “automat” summons up images of countless rows of chrome-and-glass-fronted cubicles and endless assortments of tasty dishes—not to mention the many nickels necessary to free the provisions from their cages. The automat was developed by Joseph V. Horn and Frank Hardart, who ran several lunchrooms in Philadelphia. Captivated by a Swiss-invented “waiterless restaurant” in Berlin, the duo adapted the concept for American use. In 1912, the first automat opened in Times Square, capturing imaginations and appetites for decades.

Lorraine B. Diehl and Marianne Hardart (Frank’s great-granddaughter) chronicled the chain’s culinary and social history in their charming book The Automat: The History, Recipes, and Allure of Horn & Hardart’s MasterpieceM. The authors describe the great variety of comfort food on offer; the footed metal Lazy Susans presenting catsup, mustard, salt, and pepper as well as Worcestershire Sauce and celery salt; and the fast-handed female “nickel throwers” in their glass-paneled booths. Nickel cups of coffee were dispensed from ornate metal dolphin-head spouts. The automat’s egalitarian appeal extended from shoppers to job-hunters, from down-and-outs nursing their free Depression cocktails (catsup and water) to latch-key kids, and even, on occasion, to celebrities looking for a late-night bite.

At one time, there were more than 50 automats in New York City, each with its own distinct architecture. The 57th Street outpost, which was designed in 1938 by Ralph Bencker, an Art Deco architect from Philadelphia, had curving forms and blush-pink, gold-banded terra-cotta cladding, giving the impression of a streamlined radio. When I documented it in 1982, the automat had closed, as had its successor, the discount Marboro Bookstore, which retained the automat’s “self service restaurant” nomenclature. By 1984, the New York Delicatessen occupied the site; by 1995, the Motown Café. Shelley’s New York took over in 2000, painting the gold banding black and adding a penthouse floor and garish red signage. Attempts to landmark the structure failed because not enough of the original automat remained.

The six-story building to its west (right) began life as yet another high-stooped four-story brownstone. Beyond it is 110 West 57th Street. The undistinguished brick-and-glass commercial building, topped by a lone water tower, was completed in 1949 over the structural remains of the noble 1909 Renaissance-inspired Lotos Club. It currently houses the Directors Guild of America and street-level DGA New York Theater, once the 57th Street Playhouse. To the east of the automat is the 1963 light-gray-brick co-op Carnegie House; it extends down Sixth Avenue to 56th Street and today remains almost unchanged.

Towering behind the automat on 56th Street is the 42-story Thompson Central Park hotel, formerly Le Parker Meridien of 1981, designed by Philip Birnbaum. In 2007, the automat and its western neighbor gave way for the 28-story West 57th Street by Hilton Club, which blocks the view of the Thompson Central Park. The shiny green glass facade of the Hilton Club reflects no personality of its own, only the buildings across the street.

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Chapter Six: Upper East Side

69th Street To 88th Street

My parents and I left the Upper East Side in 1944, but I returned in 1969 with my own family. For ten years, the five of us lived in a 12-foot-wide townhouse on 89th Street between Lexington and Third Avenues. Third Avenue was our Main Street, our destination for errands of all sorts. One morning in 1971, upon hearing that the east side of Third between 87th and 88th was about to be torn down, I dashed over to the friendly vendor at the Fruit House, on the 87th Street corner, to ask if it was true. He assured me it was not. But the very next day, “urban relocation” signs appeared on all the tenements on the block. As I photographed the familiar scene for a future painting, the comment of an astute wag came to mind: Those developers, they knock your block off. This particular block was knocked off in 1975 by the 30-floor Claridge House rental apartment building. Ground-floor shops front on Third Avenue; the resident entrance is not on 87th or 88th Streets, as might be expected, but hidden midway inside the back, on an unusual through-block private driveway.

The scene’s typical Yorkville turn-of-the-century tenements, except for the two on the north (left), are now gone. The Valley National Bank, on the northeast 88th Street corner, long ago modernized its two-story facility and now serves the residents of nearby pool-and-concierge skyscrapers. Just beyond it is the great-granddaddy of neighborhood hardware stores, Wankel’s, in business since 1896. Only the “ardware” portion of its side wall advertisement shows. Wankel’s, currently run by the founders’ great-granddaughter, occupies two tenements between 88th and 89th Streets. The facade is delightfully patriotic, with bright red cornices and fire escapes, vivid blue bricks, and white banding and trim.

Laurence Stelter interviewed Karl Wankel, third-generation owner of Wankel’s Hardware, in his fascinating book By the El: Third Avenue and Its El at Mid-Century. Born when the neighborhood was primarily German and Irish, the hardware merchant explained that since the ground level in this section of Manhattan is higher than it is farther downtown, the El tracks here were only 11 feet above the street. This situation made passage underneath risky. One too-tall poultry delivery truck ended up damaged, unwittingly providing a chicken for every pot in the vicinity. Also, since flat 89th Street suddenly slopes precipitously downhill toward Second Avenue, an additional flight of stairs was necessary to reach the uptown 89th Street station platform.

My son owns this painting. He insists that his childhood was deprived because I never took him to the Papaya store at the southeast corner of 87th and Third. He’s right; we never patronized it (nor does anyone anymore; the block was replaced in 1992 by a 23-story mixed-use building, 200 East 87th Street). What he doesn’t remember is that I often took him to the more popular—and still thriving—Papaya King on the northwest corner of 86th Street and Third Avenue, built in 1932. Of course I did: what mother would go home to cook a real dinner when there was a feast of hotdogs and papaya juice waiting nearby?

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Chapter Seven: Upper West Side

60th Street To 95th Street

The Loews 83rd Street movie theater, at the northeast corner of Broadway, was designed by Thomas W. Lamb in 1921. A three-story white-glazed-terra-cotta Palladian-style entry/commercial volume fronts a taller red-brick stepped-roof auditorium. Flanking the Broadway marquee are small neighborhood businesses: the Outdoorsman General Store; a tax preparer/driving school/insurance brokerage; the Pet Bowl; and Charamis Hairdressers. Headquartered on the second floor is the West Side Republican Club.

Loews 83rd became a triple-screen venue in 1976 and a quad in 1978; its last picture show took place in May 1985, with demolition soon after. The Loews Corporation had purchased the five-story apartment house directly to the north (left) and built a new movie house there by March 1985. Held & Rubin designed the three-story limestone-clad Loews 84th Street Sixplex and, in recognition of Loews’ intentions to sell the theater’s air rights, installed within it concrete pillars capable of supporting a sizeable structure above. In 1985, developer William L. Haines purchased the 83rd Street site and development rights to the sixplex. Two years later, the Bromley, an upmarket 23-story condominium, rose there. Designed by Costas Kondylis of Philip Birnbaum & Associates, the red-brick building has a three-story base clad in white limestone. The blockfront has a unified look even though the movie house is still a Loews property.

The AMC 84th Street 6 (as it is known today after a Loews/AMC Theaters merger) remains a neighborhood destination. In 1996, Rockwell Group created a New York City–themed entrance lobby. Nine years later, the auditoriums were outfitted with plush power recliners. These La-Z-Boy-style faux-leather seats, one-and-a-half-people wide, can transform from an upright seat to an almost bedlike lounge.