2. Singer Building

Source: New York Public Library

With 7% of the votes, the Singer Building came in second. Never heard of the Singer Building you say? Well, it was once the world’s tallest building. If it was still standing, you’d see it right near the World Trade Center next to Zuccotti Park and Liberty Street and Broadway. It was built in 1908, designed by the architect Ernest Flagg for the Singer Company. One reader wrote, “Singer building. It was effing gorgeous. And it was replaced with a black box that has no style or personality.”

In 1961, the Singer Company sold the skyscraper to US Steel when the company moved to Rockefeller Center. The building’s shape, a narrow tower on a base, was considered not conducive to modern real estate needs (though the setback was a deliberate design by Flagg). The red brick, limestone, and terra cotta building was demolished in 1967 and replaced by the black steel tower you see today.