1920s skyscrapers towering over Times Square

With so many skyscrapers in the city topping out with more than 70, 80, even 100 floors, the tall buildings shown in this photo of Times Square look pretty puny.

But they impressed New Yorkers at the time, and the caption on the back of the card boasts about them. “This aerial photograph of the Times Square section of New York shows many of the skyscraper office buildings located in the heart of New York,” it reads.

“Among the best known are the Times Building, the Bush Terminal Building, recently completed Loew’s State Theatre, and the famous Hotel Astor on Broadway.”

What Times Square looked like in 1911

That’s when it was still known as Longacre Square, though the name was officially changed in 1904 when The New York Times built its new headquarters there.

Looks so small-town, doesn’t it?

A Times Square postcard from the late 1940s

An Ephemeral reader sent in this supercool postcard.

The once-glam Hotel Astor is on the left. A vertical sign on its facade seems to say “Roof Astor,” a reference to the glorious roof garden that was once the place for city high rollers to see and be seen.

Great naked statues flanking the Bond store sign, right? And look closely; that’s a Woolworth’s on the ground floor.

Three ways of looking at Times Square

West 47th Street and Broadway (looking south) comes off like a frontier town in this 1878 photo. Check out the dirt roads!

At the time, it was the city’s carriage trade district, home to carriage makers and stables. Soon it would be renamed the more elegant-sounding Longacre Square, after the carriage district in London.

Things changed a lot by 1975, when the above photo was taken. Longacre Square became Times Square in 1904, and the northern end was renamed Duffy Square in 1939.

Today, Times Square the pedestrian mall still has a TKTS kiosk. But Florsheim Shoes and Burger King are gone, and gleaming glass office buildings sparkle along Broadway and Seventh Avenue.

[First two photos from New York Then and Now]

The stunning roof garden of the Hotel Astor

Times Square’s Hotel Astor, opened in 1904 on West 45th Street, was an opulent 500-room palace boasting luxurious banquet halls, terraces, tea parlors, and a Louis XV–decorated ballroom.

It also had a huge, elaborate roof garden where Gilded-Age New Yorkers dined, danced, and entertained themselves, catching cool river breezes in a pre–air conditioned era.

It’s been gone since 1967, replaced by an office tower. But back in the day, a New York Times article from 1920 had this to say:

“Down near Times Square the Hotel Astor Roof Garden and Belvedere Restaurant make it possible for the wayfarer to leave the torrid stretches of Seventh Avenue and in a few moments find himself in a real garden surrounded by flowers.

“There is the open-air dancing floor and the restaurant is conspicuous for dangling ferns and trailing vines. A unique feature of the restaurant is the gabled-glass roof over which flows a miniature Niagra.”

Times Square all lit up in Technicolor

This vintage postcard captures a rain-slicked Times Square bursting with color and light at night. It must be 1951; Ten Tall Men and Across the Wide Missouri were both released that year. 

The Automat is on the left. Who knew that its heyday as the place to go for machine-dispensed food and drink anytime of the day or night would soon be drawing to a close?

Best Times Square strip club sign ever

Who would’ve thought that Gotham City Ladies World, on 8th Avenue in the 40s, appreciated their customers so much? The sign taped to the entryway says it all. Maybe if Show World and Billy’s Topless put up something as nice as this, they’d still be open.

Here’s the image on the marquee above the ground floor, one of the last of the illustrious Times Square porno signs. The hearts on either side of the electric neon lady are a classy touch. 

“Shall we go down by the automat?”

This ad for Horn & Hardart’s automat in Times Square survives in midtown, but the automat itself is pretty much part of restaurant history. It was a terrific machine-age idea: Pop a few coins in the slot, select the dish you want, and out comes your food from one of the many compartments.

Dozens of automats thrived all over the city. But after the 1960s, fast food outlets multiplied, and, well, you know the rest. The last Horn & Hardart’s, on Third Avenue and 42nd Street, was shuttered in 1991. 

The Times Square automat was a big hangout for Beat writers. In Lonesome Traveler, Jack Kerouac writes, “Shall we go down by the automat and watch the old ladies eating beans?”