The circa 1901 photo above, which has much to recommend it, is filed at the Library of Congress under the title “The Tallest buildings in the world, New York City”. That’s half right. The building on the right is the 1899 Park Row Building, which was the tallest skyscraper at that time and for the next few years, until the Singer Tower was built. The building to its left, the 1897 St. Paul Building, was not the second tallest, as the headline suggests, but rather the fifth. When the heights of the tallest buildings increased rapidly a few years later, starting with the Singer Building, the St. Paul Building faded from public consciousness as being particularly tall.
We’re looking any the rear facades of both of those buildings, as can be seen by how very plain the masonry is; the big windows on Park Row suggest the skeleton frame within. Certainly this is not the way the architects and owners of these buildings would want them to be seen, but it gives a sense of how these intruders fit in the cityscape of older and smaller buildings.
Here’s the skyline of lower Manhattan as seen from Brooklyn around 1913 or so. (Both the Woolworth Buidling at center and the Municpal Building at right are in the final stages of construction. Singer, off to the left, was about five years old.) Note the Park Row Building just to the left of Woolworth, and St. Paul left of that, both looking a bit shorter than in the photo above.
Here are the surviving pieces of a 1911 panorama “Skyline from lake front, Chicago:
Here’s an early 1910s view of Pittsburgh’s Fifth Avenue:
It occurs to me that many of the early skyscrapers in New York, as well as the tallest buildings here in the 1910s, 20s, 30s, and again starting around 2000 fit the image of a “sky scraper”: they have some form of spire or pointed top that fits that phrase. The height-limited and blockier buildings elsewhere are more like sky-bludgeoners.
More on early skyscrapers: The Structure of Skyscrapers.