New York Songlines: 22nd Street

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Thomas Smith Park

Named for a secretary of Tammany Hall's executive committee; has a dog run, ball fields.

South:

Dia Center for the Arts

548: This art space, opened in 1987, helped transform Chelsea into Manhattan's main gallery district. Specializing in large-scale single-artist installations, it's featured the work of Joseph Beuys, Andy Warhol, Jenny Holzer and Richard Serra.

530: American Fine Arts; Brent Sikkema

522: A satellite gallery of Matthew Marks

520: Comme des Garcons; fascinating futuristic clothing store.

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Corner (162 11th Ave): Once the International Longshoremen's Association Union Hall--headquarters for the corrupt president Joe Ryan who inspired the movie On the Waterfront. Now the Sanford Meisner Theater, named for the legendary acting teacher whose students included Robert Duvall, Gregory Peck, Grace Kelly, Diane Keaton and Joanne Woodward.

559: Opus 22. On May 23, 2006, bouncer Stephen Sakai allegedly shot a man to death outside this nightclub, then confessed to another unsolved killing-- and was a suspect in a couple of other deaths. Was Open, a cafe inspired by airport lounges.

535: Marianne Boesky Gallery; Frederich Petzel Gallery; Printed Matter, promoting books as works of art

545: Dia extension gallery

525: D'Amelio Terras; 303 Gallery; Messino Wyman Projects

515: Barbara Gladstone Gallery

511: Wild Lily Tea Room; very zen.

505: Nikolai Fine Art

South:

436: Shakespearean actor Edwin Forrest lived in this house; fans of Forrest led the Astor Place Riot against British Shakespearean Charles Macready in 1849.

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Empire Diner

Corner (210 10th Ave): Classic railroad car diner dates back to 1943. Featured in Men In Black.

435: Actress Geraldine Page died at her home here, 1987.

427: Writer Sherwood Anderson lived in a cheap room here in 1918, where he liked to spend his time looking into other people's apartments.

South:

360: Editor and critic Malcolm Cowley lived in a former building here from 1930 to 1934, while he was editing The New Republic, whose offices were nearby on W. 21st Street.

318: The address of West End Records, pioneering dance music label associated with the legendary Paradise Garage.

302: Allerton Hotel; Patti Smith and Robert Mapplethorpe lived here together.

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The Onion

245 (corner): This building houses the headquarters of America's Finest News Source, which moved to New York from Madison, Wisconsin in 2001.

South:

Corner (208 7th Ave): Regional Thai Taste

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277c: Unicorn, gay porn outlet

275: Barracuda, friendly gay bar

South:

136: From 1972-74, this was the first home of This & That Gallery, a private disco.

132: The Stanwick Building houses the Irish Repertory Theater

Adams Dry Goods

Corner (675 6th Ave): Was Adams Dry Goods, upscale shop built in 1900; note "ADG" on arch. Was a Barnes & Noble from 1994-2008; Mattel Toys has its offices here.

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Corner (209 7th Ave): Restivo, Italian

161: This was the orginal home of the fabulous Upright Citizens Brigade Theater, home to various improv groups; got kicked out because the building was a firetrap. Earlier it was the Harmony Burlesque Theater, a raunchy strip club. UCBT is now at 26th and 8th.

143: Willem de Koonig's loft (1930s-40s). He washed it top to bottom every Saturday.

137: PB Cuban Cigars

135: DeMask; high-end latex fetish gear store claims to have sold Janet Jackson her Superbowl bustier--and insists it did not malfunction.

127: Second Hand Rose Music has 100,000 titles in stock.

125: Chelsea Playhouse

Corner (699-709 6th Ave): Was Ehrich Brothers (1889-1911); bargain store. Now Burlington Coat Factory, Staples.

South:

Corner (688 6th Avenue): Maffei Pizza, Sicilian lunch counter, is ''culinary nirvana,'' says the the Voice. A U.S. Army Recruiting Center is upstairs.

64: Daniele's Piadina sells Romagnese flatbread sandwiches.

62: Mosaic House sells Moroccan tiles. The mysterious Green Spa is upstairs.

60: An optical shop that's been around since 1947.

56: New York Cake & Baking Supplies, for the serious cake baker. Upstairs is Chisholm Gallery, which exhibits and sells original vintage posters.

54: Soon Beauty Lab--a spinoff of an East Village salon-- is in an intricately decorated building; note the glasswork above the entrance.

52: Derelict rowhouse--you don't see too many buildings with bricked-up windows anymore.

48: Christopher Stanley, subtle hair colorists

46: Arezzo, spendy Italian named for the setting of Life Is Beautiful. The painter Phillip Guston moved here in 1937, writing to a friend, “It's the best place we’ve ever lived in N.Y. and only 25 a month!”

44: Fancy old brownstone

36: Pascal Boyer Gallery, 20th Century decorative arts; Robert Passal Interior Design

32: Just Calm Down: A Jewel of a Spa

30: The Van Alen Institute, named for Chrysler Building architect William Van Alen, is dedicated to improving public design in New York City.

28: Site of The Ladies' New-York Club, organized in 1889

20: The zen-like Salon O2; Color Resource Center

16: Deep, the club formerly known as Ohm

4: Prey was the Star Bar, cosmic-themed lounge, and before that the neo-Polynesian Tiki Room. There's a sign here that says "Artist Residing in Building"--not sure if the sign itself is an art project or if there's actually some need for people to know this. The Dezer real estate company that owns this property has named more than one of its buildings after itself, which hardly seems fair.

Sohmer Piano Building

Corner (170 5th Ave): Zales jewelry is on ground floor of this 1898 building, noted for its gilded rooftop dome. Was a piano showroom; now houses publishing and design companies.

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The Caroline

Corner: Shopping and apartments built in 2002 on site of Edwin Booth Theater (1869-1883). This was run by and featured New York's most prominent Shakespearean actor--brother of John Wilkes Booth. Sarah Bernhardt made her New York debut here. Later James W. McCreery (1895-1907), "Dean of the Retail Trade." Demolished 1975. A bust of Shakespeare from the old theater can be seen on the new building's west side.

49: Site of the New Etching Club.

43: Manhattan Village Academy, a college prep school, is in a concrete building with interesting polychrome details. Country Home & Comfort is at the same address but in a seemingly different building--one that could not look more urban and utilitarian.

23: A handsome red brick and cast-iron building serves as an employees' entrance for Home Depot--could be put to more prominent use.

19-9: This seems to be the back side of the old Stern Brothers department store, now Home Depot.

17: Site of the Electric Club, organized in 1885 to promote electrical science and industry.

11: The address of the Harvard Club's first clubhouse, which it left in 1895.

3-7: Classic Sofa is in the Spinning Wheel Building, built over the last home of telegraph inventor Samuel Morse, who died here April 2, 1872.

1: L&I Photo & Digital is in an odd, three-story blue building.

Corner (172 5th Ave): Lucky Brand Blue Jeans. Formerly a cigar store, complete with wooden Indians.

South:

Albert Building

Block (935-939 Broadway): The building that houses Renaissance Hardware was built in 1861-62 as the Glenham Hotel by architect Griffith Thomas. Also known as the Albert or Mortimer Building. On the Broadway side, outlines of letters that once spelled out "ALBERT" can be seen. According to City Reads, this building once housed the saloon of Dr. Jerry Thomas, master mixologist (for whom the Tom and Jerry was named). Cornelius Vanderbilt Jr., son of the Commodore, shot himself here on April 2, 1882, after a night of drinking and gambling.

The long-stopped clock on the 5th Avenue corner inspired the They Might Be Giants song "Four of Two"-- though it's running now.

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Flatiron Building

Block (175 5th Ave): Built in 1903 as the Fuller Building, its unusual and striking shape (designed by Daniel Burnham to match its triangular lot) quickly earned it its lasting nickname. It is not true that is New York's first skyscraper-- just one of its most memorable. A traditional publishing center, it's home to Henry Holt and Company, a publishing house founded in 1866 that has printed such authors as Robert Louis Stevenson, H.G. Wells, Ivan Turgenev, Robert Frost, Hermann Hesse and Norman Mailer. Today its roster includes Paul Auster, Thomas Pynchon, Salman Rushdie and Barbara Ehrenreich. It also houses St Martin's Press, which "prides itself on having the largest and broadest list of any U.S. publisher, expressing the widest possible range of human experience." In the 1910s, it contained the offices of the Socialist Labor Party, ancestor of most U.S. left parties. It features in the movie Spider-Man as the Daily Bugle building, and Jimmy Stewart and Kim Novak are teleported here in Bell, Book and Candle. Origins and MAC cosmetics are the high-end businesses found on the building's relatively broad 22nd Street end.

South:

Corner (936 Broadway): This was once the site of the Buck's Horn Tavern, which as long ago as 1816 was described as "an old and well-known tavern." Later the first bicycle-riding school opened on this site in 1868. Still later it was Abbey's Park Theater, where Lillie Langtry's American debut was scuttled by the theater burning down on October 30, 1882. Present building built for Brooks Brothers in 1883--it's been "modernized" since. Now houses Domain interiors.

12: Borough was Caviar & Banana Brasserio, Brazilian, which replaced the short-lived Rocco's, subject of the NBC "reality" show Restaurant. Earlier was the ironic Commune, a popular spot for the characters on Sex and the City.

22: Was Alva, swanky bar with too many cigar smokers

24: Miwa Alex, hair salon whose co-owner claims to take inspiration from Michelangelo

26: Was Pauline Yeats home interiors

36: Kitchen 22; the owner of Aureole and Metrazur offers a $25 prix fixe here. (Time Out calls this New York's "best value"-- haven't they heard that the dot.com boom is over?)

38: The New York Kids Club

Corner (276-278 Park Avenue S): Gramercy Place was the 1894 Bank for Savings (as the stone still notes), saved from demolition in 1987 by the placement of a high-rise apartment on top. Associated Supermarkets on the ground-floor corner.

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Madison Green

5: Very large luxury condo building was built after Wonder Drugs Fire of October 17, 1966, which killed 12 firefighters--the worst disaster in FDNY history until the World Trade Center attacks.

21: Princeton Ski Shops, founded in 1916, originally specialized in figure-skating equipment.

23: Bolo, hip Spanish--also featured on Sex and the City

29: Stupell International, china

33: In 1903, this was the National Christian League for Promotion of Social Purity.

43: Tamarind, fancy Indian

45: Beppe, expensive Italian, has the best ribs in town, says the Village Voice

Corner (300 Park Avenue South): The Mills & Gibb Building, a 15-story building from 1910 designed by Starrett & Van Vleck for the Mills and Gibbs linen store. Note waterbaby carvings. Built on the site of the 4th Avenue Presbyterian Church. Wilhelmina, a modeling firm founded in 1967 by model Wilhelmina Cooper, is based here.

South:

Protestant Welfare Agencies Building

Corner (281 Park Avenue S): Robert Gibson's lovely 1894 building, seemingly all pillars and arches, was originally the (Epicopal) Church Missions House. Note frieze above entrance depicting St Augustine preaching to the Saxons, and Bishop Seabury preaching to the Indians-- we were heathens once, too, is the message.

102: The Gramercy Arms is a 10-story brown-brick apartment building built in 1928, with creative brickwork and beautiful terra-cotta tiles. An extraordinary example of what can be done with an ordinary building. On the ground floor is Novita, modern Italian.

The back of 60 Gramercy Park

118: Site of the house of architect Isaac Newton Phelps Stokes, who designed Columbia's St. Paul's Chapel and wrote the six-volume Iconography of Manhattan Island.

120: Site of composer Charles Ives’ home.

Sage House

Corner (4 Lexington): Built to house the Russell Sage Foundation, started in 1915 by Olivia Sage to coordinate the dispersal of the fortune she inherited from her tight-fisted husband. "For the Improvement of Social and Living Conditions" can still be read on the frieze, which features emblems of civic virtues--Health, Work, Study, Play, Housing. From 1949-76 it was the Catholic Charities Building; now apartments.

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United Charities Building

Corner (287 Park Avenue S): This marvelous pale-brown building, built in 1891 to an R.H. Robertson design, was the site of the founding of the NAACP on May 31, 1909. It still houses charities like the Community Service Society.

111: Built in 1915 as an annex to the United Charities Building, it originally held the New York School of Philanthropy, then from 1946 to the 1980s it was the headquarters of the Dockbuilders Union. It now houses Elite Model Management, which has represented perhaps more supermodels than any other agency, including Cindy Crawford, Claudia Schiffer, Kate Moss, Linda Evangelista and Naomi Campbell. BLT Prime, part of Laurent Tourondel's burgeoning empire, is opening on the ground floor.

115: The back of United Cerebral Palsy of NYC's building

School of the Future

127 (corner): A progressive middle school/high school that emphasizes integration of technology into all academic work. Built as the Manhattan Trade School for Girls in 1919, it was designed by CBJ Snyder in the Collegiate Gothic style and built largely out of white terra cotta.

South:

Corner (7 Lexington): Park Gramercy apartments, drably generic building put up in 1951 (though some claim it has redeeming Art Deco features), replacing the former corner, No. 9, which had been the home of Peter Cooper, who ran first the U.S. railroad (the Tom Thumb), helped lay the trans-Atlantic telegraph cable and invented Jello. He founded the Cooper Union for the Advancement of Science and Art, which to this day continues to charge no tuition. Cooper died here on April 4, 1883, and the house was inherited by his son-in-law, Abram Hewitt, a New York mayor (1886-87) who opposed Tammany Hall and promoted the building of subways. The crafts collected here by Hewitt's daughters, Eleanor and Sarah, became the core of the Cooper-Hewitt Museum.

134: Fresh out of Yale, Cole Porter lived and threw many parties at an earlier apartment on this site (1916-17). Now Gramercy Row, a 1975 apartment building with notable balconies.

144: The Lexington, a 1901 Beaux-Arts apartment building that is one of the very first New Law tenements, planned almost immediately after the Tenement House Act went into effect.

150: An 1893 carriage house with a stepped Dutch gable, designed by Sidney V. Stratton for Miss E.L. Breese.

152-156: Gramercy Court, a 1907 apartment house with an eclectic style.

Corner (280 3rd Ave): Building dates back to c. 1845.

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Baruch College

135 (corner): This building, now housing the administrative offices of CUNY's business school, was built in 1939 as the Family Court Building. Aluminum bas reliefs by H.P. Camden reflect various functions of the family--education, protection, nutrition, etc.

137: Built as the Children's Court in 1916, this Classical Revival building now houses Baruch's Steven L. Newman Real Estate Institute.

145: A 1940 Colonial Revival apartment house.

151: Gustavus Adolphus Swedish Lutheran Church, dedicated in 1887, was designed by Josiah Cleveland Cady, who also designed the Natural History Museum.

155: An 1889 Queen Anne-style apartment building, since 1947 the Gustavus Adolphus parish house. Painter John Sloan reportedly lived in this building in 1911-12.

Corner (282 3rd Ave): Lamarca Pasta was Pippin's restaurant

South:

Corner (281 3rd Ave): Rolf's German-American Restaurant seems like a 19th Century survivor, but it actually dates back to the late 1960s.

220: A quirky apartment building--it appears that a former mansard roof has been partially absorbed by later additions.

234: The Epiphany School, a Catholic school connected to the church next door, was founded in 1869; this building dates to 1888.

Church of the Epiphany

Corner (373 2nd Ave): Roman Catholic church built 1967, replacing an older church destroyed by fire; one of the rare successful examples of modernist religious architecture. Built on the site of Rose Hill, the mansion of Horatio Gates, the Revolutionary War general who won the Battle of Saratoga, arguably the most important victory of the war. This neighborhood is sometimes referred to as Rose Hill, though few New Yorkers could tell you where that is.

The Epiphany Peace Garden is a memorial to the parishioners, neighbors and local police and firefighters who died in the September 11 attacks.

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Corner (283 3rd Ave): Lyric Diner

205: Gramercy Park Habitat, a robust red-brick building from 1896.

A quite beautiful garden here seems to be reserved for Gramercy House residents.

Corner (381-387 2nd Ave): Gramercy House apartments have cool deco trim. Comprises Bruno Ravioli (No. 387), The French Butcher (No. 383B) and Gramercy Fish Co. (No. 383A).

South:

310 (corner): Building with green polychrome details houses medical facilities like Gramercy MRI Associates, NYU's Faculty Practice MRI, NYU's Department of Physical Therapy and the Phillips Beth Israel School of Nursing. The Madison Square Boys & Girls Club used to have its 22nd Street Clubhouse in the basement.

312: Gramercy East Condominium

342: Broken Cup, cozy cafe

Corner (375 1st Avenue): Stuyvesant Deli News & Smokes, formerly PB Deli & Grocery

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301 (corner): Gramercy Food Market is on the ground floor of the ugly white-brick apartment building.

327: Ungar House, foster housing for LGBT youth, is dedicated to John Ungar, "who believed in the dignity of children."

Corner (377 1st Avenue): Lucky Chicken, formerly Chirping Chicken

South:

Peter Cooper Village

420-440: Built in the late 1940s by Met Life Insurance Co. as affordable housing; now being converted to luxury condos. Built on the site of the notorious Gashouse District, where fumes from chemical plants kept out all but the poorest immigrants. Terrorized by the Gashouse Gang.

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Peter Cooper Village