New York is nev­er just one city; it’s always sev­er­al, inter­act­ing with – or push­ing out – each oth­er. This goes for the city’s archi­tec­ture as much as for its pop­u­la­tion. Its stra­ta of pub­lic works projects, cul­tur­al insti­tu­tions, depart­ment stores, hotels, hos­tels, hous­ing, and sky­scrap­ing office build­ings tell the sto­ry of its evo­lu­tion. Now, artists, urban­ists, and archi­tects protest face­less con­dos and big box stores. In decades past, they fought the face­less tow­ers that rose into the atmos­phere and blocked the sun. Such oppo­si­tion stretch­es back well over 100 years, to the turn-of-the-cen­tu­ry New York of the Flat­iron Build­ing and Beaux Arts won­ders like Penn Sta­tion, a build­ing, The New York Times writes, that “once made trav­el­ers feel impor­tant.”

“In the 1890’s,” writes Christo­pher Gray, Paris-trained archi­tect Ernest Flagg “denounced the grow­ing crop of sky­scrap­ers, and by the turn of the 20th cen­tu­ry he was hor­ri­fied by the dark­ened streets and raw side walls pro­duced by such build­ings.” Flagg’s opin­ions were of lit­tle inter­est to his New York employ­ers, so he “shift­ed his focus to reform­ing sky­scraper design” instead of decry­ing them out­right.

The endeav­or pro­duced a mod­ern mar­vel, “a one-of-a-kind tow­er” ris­ing above the New York City sky­line, notes the video above, “a total mas­ter­piece of archi­tec­ture and engi­neer­ing unlike any­thing seen before” — the Singer Tow­er, built for the Singer Sewing Machine Com­pa­ny in 1908.

So impres­sive was it for its time that Flag­g’s build­ing won com­par­isons to the pyra­mids of Ancient Egypt. For a brief moment, between the years 1908 and 1909, it was the tallest build­ing in the world, until it lost the title to the Met­ro­pol­i­tan Life Insur­ance Com­pa­ny Tow­er, anoth­er unusu­al build­ing unlike the rec­tan­gu­lar sky­scrap­ers against which Flagg railed. Uncon­cerned with max­i­miz­ing avail­able real estate, he “urged that sky­scraper tow­ers more than 10 or 15 sto­ries high should be set back from the prop­er­ty lines, so that the tow­er occu­pied only one-quar­ter of the lot,” writes Gray. “All four sides could then be treat­ed archi­tec­tural­ly, and ‘we should soon have a city of tow­ers instead of a city of dis­mal ravines.’ ”

Work­ing in a Beaux-Arts style, Flagg put his the­o­ries to the test in the Singer Tow­er, also called the Singer Build­ing, expand­ing an orig­i­nal 10-sto­ry base to 14 sto­ries, then build­ing a small­er 33 ‑sto­ry tow­er atop it. Capped by a dome with a lantern and flag­pole ris­ing from it, the tow­er’s “bul­bous top became one of New York’s best known land­marks.” Its lob­by had the ornate lux­u­ry “seen in world’s fair and expo­si­tion archi­tec­ture of the peri­od.” But Flag­g’s vision of “a city of free-stand­ing tow­ers” would remain the dream of a sin­gle archi­tect. Despite his work for leg­is­la­tion to curb sky­scrap­ers that took up entire city blocks, such build­ings, includ­ing the 34-sto­ry City Invest­ing Build­ing, would con­tin­ue to rise around the dis­tinc­tive Singer Tow­er.

Final­ly, Flag­g’s quirks proved too much for New York’s real estate elite. When the Singer com­pa­ny moved its head­quar­ters in 1961, inter­est in the Tow­er remained low “because the small square footage of the build­ing’s nar­row tow­er was anti­thet­i­cal to the boom­ing growth of mod­ern busi­ness, which demand­ed more, not less, office space,” writes Katie Hiler. Decon­struc­tion of the first sky­scraper “ever to be peace­ful­ly demol­ished” began in 1967, five years after the demo­li­tion of Penn Sta­tion. In place of the Singer Tow­er would rise the 54-sto­ry One Lib­er­ty Plaza, a har­bin­ger of things to come in the city’s new finan­cial hub, the World Trade Cen­ter.

Relat­ed Con­tent: 

Watch the Com­plete­ly Unsafe, Ver­ti­go-Induc­ing Footage of Work­ers Build­ing New York’s Icon­ic Sky­scrap­ers

The Sto­ry Behind the Icon­ic Pho­to­graph of 11 Con­struc­tion Work­ers Lunch­ing 840 Feet Above New York City (1932)

An Intro­duc­tion to the Chrysler Build­ing, New York’s Art Deco Mas­ter­piece, by John Malkovich (1994)

Josh Jones is a writer and musi­cian based in Durham, NC. Fol­low him at @jdmagness

This month brought the 20th anniver­sary of Sep­tem­ber 11, 2001, which prompt­ed peo­ple around the world to remem­ber all that was lost on that day. The fall­en Twin Tow­ers of Minoru Yamasak­i’s World Trade Cen­ter have only gained sym­bol­ic res­o­nance over the past two decades, despite hav­ing been unloved when they still stood. “They often appeared to New York­ers like a pair of mid­dle fin­gers — to good devel­op­ment, to good eco­nom­ics, to good taste,” writes Gothamist’s Hen­ry Stew­art. “They brought all, high and low, rich and poor, togeth­er to hate.” Some crit­ics of the World Trade Cen­ter made com­plaints root­ed in pol­i­tics, finance, and urban design; most just did­n’t like how the thing looked.

For 28 years, what the World Trade Cen­ter in gen­er­al and its Twin Tow­ers in par­tic­u­lar sym­bol­ized was all that the Amer­i­can pub­lic detest­ed about what it thought of as the out­landish scale, aes­thet­ic drea­ri­ness, and sheer inhu­man­i­ty of “mod­ern archi­tec­ture.” But as Bet­ty Chen of ARTic­u­la­tions points out in the video above, there’s mod­ern archi­tec­ture, and then there’s Mod­ern Archi­tec­ture.

“A tru­ly Mod­ernist design,” she says, “adheres to a strict set of for­mal rules that upholds Mod­ernism’s fun­da­men­tal prin­ci­ple: form fol­lows func­tion.” Such Mod­ernists as Wal­ter Gropius, Lud­wig Mies van der Rohe, and Le Cor­busier sub­scribed to the notion that “archi­tec­tur­al design should be dis­as­so­ci­at­ed from his­toric ref­er­ence, be free of unnec­es­sary orna­men­ta­tion, and be sim­pli­fied to the essen­tials of func­tion.”

As ver­sions of these prin­ci­ples for rebuild­ing a new post­war civ­i­liza­tion — vul­gar­ized ver­sions, some might say — caught on in the mid­dle of the 20th cen­tu­ry, cities around the world set enthu­si­as­ti­cal­ly about putting up “emp­ty box­es of noth­ing­ness.” Or so argued Mod­ern Archi­tec­ture’s detrac­tors, who gained the cul­tur­al upper hand short­ly there­after. “If the first half of the 20th cen­tu­ry is con­sid­ered to be the age of Mod­ern Archi­tec­ture,” says Chen, “then the lat­ter half of the cen­tu­ry can be defined by a con­tin­u­al, unre­lent­ing assault on Mod­ern Archi­tec­ture.” That assault includ­ed the demo­li­tion of anoth­er of Yamasak­i’s mid-cen­tu­ry projects, the Pruitt-Igoe hous­ing com­plex, which began on March 16, 1972. Though car­ried out with­out mur­der­ous intent, it did involve a notable death: the death, as archi­tect Charles Jencks famous­ly declared, of archi­tec­tur­al Mod­ernism itself.

Relat­ed Con­tent:

Every­thing You Ever Want­ed to Know About the Beau­ty of Bru­tal­ist Archi­tec­ture: An Intro­duc­tion in Six Videos

The World Accord­ing to Le Cor­busier: An Ani­mat­ed Intro­duc­tion to the Most Mod­ern of All Archi­tects

How the Rad­i­cal Build­ings of the Bauhaus Rev­o­lu­tion­ized Archi­tec­ture: A Short Intro­duc­tion

A Quick Ani­mat­ed Tour of Icon­ic Mod­ernist Hous­es

Watch 50+ Doc­u­men­taries on Famous Archi­tects & Build­ings: Bauhaus, Le Cor­busier, Hadid & Many More

1,300 Pho­tos of Famous Mod­ern Amer­i­can Homes Now Online, Cour­tesy of USC

Based in Seoul, Col­in Mar­shall writes and broad­casts on cities, lan­guage, and cul­ture. His projects include the Sub­stack newslet­ter Books on Cities, the book The State­less City: a Walk through 21st-Cen­tu­ry Los Ange­les and the video series The City in Cin­e­ma. Fol­low him on Twit­ter at @colinmarshall or on Face­book.