7. The Singer Building
The Singer Building rising in the background, behind City Investing Building (both have been since demolished). Image from Library of Congress.
In 1967, the Singer Building, once the tallest in the world, was the tallest building ever to be demolished. It remains to this day the third-tallest building ever to be destroyed after the World Trade Center towers. The Singer Building was sold in 1961 by the Singer Company to US Steel, a few years before the creation of the Landmarks Preservation Commission and was never granted landmark status. Prior to demolition, extensive photo documentation of the lobby was done before demolition which we fortunately still have today at the Library of Congress. The Singer Building was replaced with the US Steel Building (now One Liberty Plaza) which still stands today.