As ardent as New York’s architectural preservation movement is today, historians are quick to remind us that it wasn’t always this way. With the skyscraper boom of the early 20th century and then the modernist construction fervor of the 1960s and 70s, a number of extraordinary buildings met their untimely demise, making way for the city we know today. Perhaps the most famous of these, and one that still haunts architectural historians and city residents alike, is the demolition of the original Pennsylvania Station, whose dismantling was met with a now-famous New York Times editorial pronouncing: “A city gets what it wants, is willing to pay for, and ultimately deserves.” But for as many unfortunate parables, there are victories to be celebrated, and extraordinary structures to be remembered. Here, 12 remarkable buildings that once grazed the New York City skyline.