From 1909, we’ve got some amazing sketches of the view from the Singer Building, created to show how wonderful it would be to have an office there. South:

West:

North:

East:

I’m not going to go into detail about all the buildings you can see, as I’ve done so many times before. But these appear to be pencil sketches, which suggests that either the artist was an obsessive beyond all reason, or that he was working from photographs rather than standing at windows.
I will point out one interesting item in the view south. The foreground on the right, just above the words “From the Singer Tower” has 115 and 111 Broadway, the US Realty and Trinity near-twins. Past them is the large lot with Trinity Church (just visible) and beyond it is the Empire Building at 71 Broadway. To the right, we’re looking at the back of 2 Rector Street, with its deep light court. To the left of Trinity’s spire is the American Surety Building at 100 Broadway. In other words, the church and yard were pretty well boxed in by high-rises in the space of about 14 years from when American Surety, the oldest of the group, was built.
One last comment: the artist was Edward William Spofford, and be sure to use his middle name to distinguish him from Edward V. Spofford, who created somewhat similar art, but was 14 when these drawings were made.

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