In one of the most “meta” film openings to ever grace the silver screen — written and directed as only New York City’s greatest auteur, Woody Allen, could — Isaac, a comedy writer (played by Allen) struggles to pen the first few lines of his next masterpiece. Set to the nostalgic swells of “Rhapsody in Blue,” we hear his musings over a stunning black-and-white montage of 1970s New York. The writer written by a writer and played by a writer ponders the perfect introduction: “To him, no matter what the season was, this was still a town that existed in black and white and pulsated to the great tunes of George Gershwin.” The Jazz Age is, of course, long gone, as is Allen’s Manhattan , but their spirit lives on in the tangled, complex web that is the electric essence of the greatest city on Earth.

Join us as we take a trip down memory lane to recall what those earlier (better?) days looked like. From a building symbolically battling for greatness on Newspaper Row to the first (and second) incarnation of Madison Square Garden, click through to check out The Big Apple’s beautiful, lost buildings. Dear readers, what do you think? Should we have preserved these beauties, or is progress inevitable? Is the city today the most magnificent it’s ever been?

Pennsylvania Station by McKim, Mead and White – Manhattan

Images via ATDLines; TransportationNation; Maud Newton

The controversial demolition of the grand pink granite station some 50 years after its opening was the catalyst for the enactment of the city’s first architectural preservation statutes. Inspired by the Roman Baths of Caracella, its enormous main waiting room approximated the scale of St. Peter’s nave in Rome. It was the largest indoor space in New York City and — covering more than seven acres — one of the largest public spaces in the world.

Vincent Scully, Sterling Professor Emeritus of the History of Art and Architecture at Yale University (and one of the most influential architecture teachers ever according to Pritzker Prize winner Philip Johnson!), summed up the resentment by saying, “through it one entered the city like a god. One now scuttles in like a rat.”

Ebbets Field by Clarence Randall Van Buskirk – Brooklyn

Image credit: Ballpark Prints; Bob Henriques via Artspace

When Walter O’Malley, then owner of the Brooklyn Dodgers, decided to move the team to sunnier shores, a federal judge said that the removal of the franchise was “one of the most notorious abandonments in the history of sports.” Based in Brooklyn’s Flatbush community, the talented team outgrew their cozy stadium, and instead of keeping them near to their dear devoted Brooklyn fans — Atlantic Yards was presented as an option, but the New York Building Commissioner wanted a new stadium to be built in Queens instead, and a stubborn O’Malley refused — they ended up in Los Angeles.

The historic field was demolished in 1960 and replaced with apartment buildings.

Singer Tower by Ernest Flagg – Manhattan

Images via: whitewall buick

Singer Tower was a 47-storey office building completed at the turn of the last century that at the time was not only the tallest building in New York City, but also briefly held the title of tallest office building in the world — until it was surpassed by Philadelphia City Hall. It was demolished in 1968, and is now the site of One Liberty Plaza.

New York Tribune Building by Richard Morris Hunt – Manhattan

Image credit: PrintCollection; John Feulner via Historic American Buildings Survey; downtownexpress

One of the first high-rise elevator buildings in the city and a possible candidate for the first ever skyscraper, The New York Tribune Building was sandwiched between the Pulitzer Building — home to the New York World newspaper — and the New York Times Building on a stretch of Park Row dubbed Newspaper Row because most of the city’s newspapers occupied the street, conveniently located close to any and all action at nearby City Hall. The building was demolished in 1966 to make room for the 1 Pace Plaza building. All that remains is a statue of Benjamin Franklin holding a copy of his Pennsylvania Gazette, commemorating the publishing prowess that once was.

New York Herald Building by Stanford White – Manhattan

Images via Daytonian in Manhattan

After fleeing to a self-imposed exile in Paris after embarrassing himself by urinating in the fireplace of his future in-laws (needless to say the engagement was terminated), the playboy son of the Herald’s founder, James Gordon Bennett, Sr., made the rebelliously decision to move their headquarters away from the stiff competition on Newspaper Row to points north. The infamous Stanford White of McKim, Mead & White accepted the commission for a new building based on the Venetian Renaissance Palazzo del Consiglio. As the Daytonian in Manhattan reports, the eccentric son of the publishing powerhouse “had become obsessed with hoot owls. He had run editorials in the New York and Paris editions of the Herald fighting for the preservation of the species. The owl became the symbol of the newspaper. Along the roofline he had twenty-six four-foot bronze owls installed.”

The critics were unanimous: the most expensive newspaper building in the world was a show stopper. The architectural gem didn’t last long. Just 30 years after it opened its doors, it was reconfigured and renovated beyond recognition.

The Vanderbilt’s Petit Château by Richard Morris Hunt – Manhattan

Image via: nyc-architecture; Wikipedia

The design of this château-esque mansion at 660 Fifth Avenue was overseen by William Kissam Vanderbilt’s wife, Alva Vanderbilt, a Victorian-era Francophile whose petit Renaissance-style château served as inspiration for many mansion designs across the country. Surely such a project consumed a great deal of her time, but oddly she barely mentioned its tragic demolition in her memoirs.

Hotel Astor – Manhattan

Image via skyscraper city; Endless Streams and Forests

Located in Times Square, Hotel Astor was the Waldorf-Astoria’s successor. Complete with elaborately decorated public rooms and a roof garden way ahead of its time, its 1000 guest rooms occupied 11 Beaux-Arts stories topped off by a green copper mansard roof. As the Daily News reports, it was “advertised as The World’s Most Electrified Hotel, boasting 14,000 lightbulbs and thermostatic heat control.” The Astor set the pattern for a new species of popular hotels that soon clustered around Times Square, vast amusement palaces that catered to crowds with scenographic interiors that mirrored the theatricality of the Great White Way.

Despite being such a vital component of the city’s history, sadly, the building was razed in 1968.

Fox Theatre – Brooklyn

Image via: cinema treasures

With seating for some 4,300 patrons, Brooklyn’s Fox Theatre went through many ups and downs before finally being demolished in 1970 after sitting vacant for over two years. It was later replaced by a ConEd building.

Thatched Cottage by Olmsted and Vaux – Brooklyn

Prospect Park has always housed an odd assortment of rustic and classic elements. One early building belonging to the rustic variety was a whimsical thatched shelter fondly referred to as the “Swiss Thatched Cottage.” The perfect backdrop for a picnic or a game of croquet, the funny little building unfortunately burned to the ground in 1937. It was never rebuilt.

Temple Emanu-El by Leopold Eidlitz and Henry Fernbach – Manhattan

Image via: Robert Buchanan; nyc-architecture

Designed by Leopold Eidlitz — who is often credited with being the first Jewish architect in America — this Gothic-Moorish structure was decorated with bright yellow brownstone underneath alternating red and black tiled roofs. Also a noted critic, he was fond of saying that “American architecture is the art of covering one thing with another thing to imitate a third thing which, if genuine, would not be desirable.” Ironically, one of his great masterpieces was leveled at the turn of the 20th century, preserved only in postcards.

Madison Square Garden – Manhattan

Image via The Bowery Boys

Located at East 26th Street and Madison Avenue, this open-air arena presented flower shows, beauty contests, music concerts, illicit boxing matches, the circus, and, notably, the first Westminster Kennel Club Dog Show. The roofless Garden was too hot in the summertime and too cold in the wintertime, so it was demolished and replaced by a showy new arena lovingly known as Madison Square Garden II.

Madison-Square Garden II by Stanford White – Manhattan

Image via Daytonian in Manhattan; Wikipedia

The second incarnation of Madison Square Garden was designed and built by the exceedingly talented Stanford White. It hosted numerous events, including orchestral performances, light operas, romantic comedies, the annual French Ball, both the Barnum and the Ringling circuses, and the Democratic National Convention in 1924. It was also the crime scene of the very first Trial of the Century, where a jealous millionaire husband shot said talented Stanford White point blank with a solid gold revolver for having an affair with his beautiful, buxom wife, the famous actress Evelyn Nesbit. The clandestine affair and notorious murder inspired the now famous love crime drama film The Girl In The Red Velvet Swing starring Ray Milland and Joan Collins.

On par with the destruction of the original Penn Station, the demolition of White’s Madison Square Garden in 1925 is considered one of New York’s greatest acts of architectural vandalism.