3. The Drake Hotel/432 Park Avenue

The Drake Hotel never officially achieved landmark status but before it was demolished, but it was one of the most recognizable and distinguished hotels on Park Avenue. It hosted many popular icons including Frank Sinatra, Muhammad Ali and Jimi Hendrix and was the preferred site for Led Zeppelin whenever they played in New York. It was also the site of scandals: in 1973 slightly over $200,000 was stolen from Led Zeppelin’s safety deposit box in the building.

New York City real estate developer Harry Macklowe purchased the property for $440 million in 2006. 432 Park Avenue, at one point one of the tallest residential buildings in New York City, has risen in its place.