6. Old Waldorf Astoria Hotel

Old Waldorf-Astoria Hotel circa 1901. Photo by A. Loeffler from Library of Congress.

In the spring of 1928 Billy goes to senior prom with his first steady girlfriend in the old Waldorf-Astoria Hotel, which was located at 34th Street and 5th Avenue. Shapiro describes the scene:

Billy’s senior prom started Friday, May 4, at eight thirty, in the big dance hall at the Waldorf-Astoria Hotel, with music by the Dick Stiles Orchestra. It was a relief to not enter the floor as a stag begging for a dance…that May night, the hall was bathed in fragrance, with flowers at every table and girls in evening gowns with flowers pinned in their hair gliding over the dance floor with their escorts, each, like Billy, wearing a boutonnière. The student newspaper the Textilian‘s final issue for the year called the evening perfect down to the last waltz.”

Not to be confused with the current Waldorf Astoria, the original hotel was demolished in 1928 and replaced by the Empire State Building. The hotel, the largest in the world when it opened in 1897, was built on the site of the Astor family mansion and designed by architect Henry Hardenbergh, who would later design The Dakota apartments.