Singer Building, 1913.

The Singer Building, constructed for the Singer Sewing Machine Corporation, was originally constructed as a small red brick building with a mansard roof in 1896. Designed by Ernest Flagg, the building was later incorporated into the larger, more well-known Singer Building, also designed by Flagg and completed in 1908. For a single year (1908-1909) it was the tallest building in the world. At 47-stories (the base was only 12 stories, while the tower topped out at 612 feet), the building was quickly surpassed by the Metropolitan Life Tower on 23rd Street.

Visitors to the building could pay 50 cents to take in the view from the 40th-floor observation deck. The Beaux-Arts building had a marble columned and bronze trimmed lobby and was described by architectural historian Christoper Gray as having "celestial radiance."

The building was sold in 1961 to Webb & Knapp, a real estate development company, who attempted to have the New York Stock Exchange moved into the structure. That bid was unsuccessful and in 1964 U.S. Steel purchased the building. It was demolished in 1967 (two years after the Landmarks Law was passed). Today the site is occupied by One Liberty Plaza, a 54-story office building completed in 1973.

The Singer Building remains the tallest structure to be intentionally demolished.