King Kong (1933)

King Kong is a 1933 film directed by Merian C. Cooper starring Fay Wray, Robert Armstrong and Bruce Cabot. The story is about a nautical expedition that finds a giant gorilla on Skull Island in the south Indian Ocean. The ape is brought back to New York City and put on display. Kong escapes and rampages through Manhattan until he's cornered at the top of the Empire State Building where a squadron of biplanes attack him until he falls to his death in a famous sequence.

Curtiss F8C-5/O2C-1 Helldiver
A small squadron of these biplanes attack Kong at the top of the Empire State Building.