from perplexity.ai:
Yes, an airplane did crash into the Empire State Building. On July 28, 1945, a B-25 Mitchell bomber of the United States Army Air Forces crashed into the north side of the Empire State Building in New York City while flying in thick fog. The plane struck the building around the 79th floor, creating a large hole and causing a fire that spread over multiple floors. The crash resulted in 14 deaths, including the three crew members on the plane and 11 office workers in the building, as well as many injuries. Remarkably, the steel structure of the Empire State Building withstood the impact and remained standing. One notable survivor was Betty Lou Oliver, an elevator operator who survived a 75-floor fall in an elevator shaft caused by the crash.
<holy shit