9. Flatiron Building by Joseph Pennell

Flatiron Building From Fifth Avenue and Twenty-Seventh Street” (ca. 1904-1908) by Joseph Pennell Via Library of Congress Prints and Photographs Online Catalog

One of the first skyscrapers in New York that captured the public’s imagination was the Fuller Building, located on the triangular block at Fifth Avenue, Broadway, and 23rd Street. Due to its distinctive wedge shape it immediately became known as the Flatiron Building. Designed by Chicago architect Daniel Burnham, the building, with its dramatic setting at a crossroads intersection and facing Madison Square Park, also became a favorite of artists.

“The Flat Iron” (1904) by Joseph Pennell Via NY Public Library Digital Collections

One of those under the spell of the Flatiron was Joseph Pennell (1857-1926), a Philadelphia native who lived in London for many years before moving to New York. His Flatiron works are among his most famous in a decades long career that included other New York scenes as well.