What: Forms of Transit.
Why: Clad in his top hat and coat, the gentleman in the carriage is particularly dapper while the scene around him suggests a world that was becoming ever more cosmopolitan, evidenced largely by the large double decker bus behind.
When: Judging by other shots in the batch whose dates can be pinpointed, this seems to be Winter 1939 or 1940.
Where: New York, NY. The Fifth Avenue location was pretty easy to identify. Not only is there a street sign at the right that can be made out, but the bus also shows its routing as being via 5th Avenue. I had expected this to be much further South however, and began my searches at 29th Street, only to discover this to be considerably more northward in location, spotting in at 82nd Street, in front of MoMa!
Who: Regrettably, no identifier for this gentleman.
How (much): One of a batch of 9 I got for about $20.00 on ebay a few months back. Others can be seen in some previous episodes that date back as far as 1938!