The building was commissioned by Frederick Bourne, the head of the Singer Sewing Machine Company, who hired architect Ernest Flagg, an early proponent of the Beaux-Arts architectural style. Flagg had also designed the company's still-extant previous headquarters at 561 Broadway between Prince and Spring Streets—in what is now SoHo, Manhattan—which was referred to as the "Little Singer Building" after the new building was erected. Plans and working drawings were prepared by George W. Conable. Flagg believed that buildings more than 10 or 15 stories high should be set back from the street, with the tower occupying only a quarter of the lot. The 12-story base of the building filled an entire blockfront, while the tower above was relatively narrow. The tower floors were squares 65 feet on a side. New York Times architectural critic Christopher Gray wrote in 2005:
The lobby had the quality of "celestial radiance" seen in world's-fair and exposition architecture of the period, as the author Mardges Bacon described it in her 1986 monograph "Ernest Flagg". A forest of marble columns rose high to a series of multiple small domes of delicate plasterwork, and Flagg trimmed the columns with bronze beading. A series of large bronze medallions placed at the top of the columns were alternately rendered in the monogram of the Singer company and, quite inventively, as a huge needle, thread and bobbin.
In 1961, Singer sold the building and subsequently moved to Rockefeller Center. The building was then acquired by real estate developerWilliam Zeckendorf, who sought unsuccessfully for the New York Stock Exchange to move there. In 1964, United States Steel acquired the building, along with the neighboring City Investing Building, for demolition. By the 1960s, the building was uneconomical because of its small interior dimensions. The tower portion of the building contained only per floor, compared with per floor of the building that replaced it, the U.S. Steel Building. One Liberty Plaza had more than twice the interior area than the two former buildings combined. Although New York had a newly created Landmarks Preservation Commission by the time demolition commenced in 1967, and the Singer Building was considered to be one of the most iconic buildings in the city, it did not receive landmark designation, which would have prevented it from being torn down. Alan Burnham, executive director of the commission, said in August 1967 that if the building were to have been made a landmark, the city would have to either find a buyer for it or acquire it. Demolition commenced in August 1967 and was completed the following year. At the time, it was the tallest building ever to be destroyed, a record it held until the September 11, 2001 attacks, when the nearby World Trade Centercollapsed. It remained the third-tallest building to be destroyed, and the tallest to be destroyed by its owners, until 2019, when deconstruction of the 270 Park Avenue building started in midtown Manhattan.
