http://www.brooklynpix.com/catalog09f.php?locality_no=12611 Check out what happens when one of them birds comes down in Borooklyn

I'm guessing 1939. The wing says MD, McDonell Douglas, which would make it a DC4. I was going to say 1956, but the limited number of skyscrapers makes me scale back in time. Is this a Bourke White photo maybe taken to honor technology at the time of World's Fair?

good call on the triple tail, must be 1939 indeed.

DC-4E, note the triple tail, flew only in 39', sold to the japanese and was successfully reverse engineered.

I would think that there would have been airspace restrictions during the war, so I'll say 1938....

DC-4 flying over New York City, 1939 photographed by Margaret Bourke White for Time.

I agree with Jack D. Ripper, looks like 1939.

1896

1940, just after la guardia opened.

September 11, 1948

1939, DC-4.

1947

3rd Ave el train closed in 1955. I'm gonna say... eh 1955.

1941.