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The Skyline Paintings of Dorothy McEntee

By Katie Ott

Dorothy McEntee’s watercolors of the New York Skyline from Brooklyn Heights each tell a different story of the skyline. McEntee painted these watercolors between 1935 and 1983. As one looks through them, one notices the skyline changing over time. Most of McEntee’s paintings display a realistic image of the skyline, but it is important to note she did not aim for her paintings to be documentary. She instead wanted to portray an essence of the skyline by capturing its vibrant energy and life and the emotion behind it. The titles of her paintings point her audience towards what she is attempting to convey in each of her pieces. Although all of her watercolors display the same scene, each one conveys a different message about New York and the New York skyline.

This 1944 painting entitled “Wartime Smoke” is unique among Dorothy McEntee’s paintings because the skyline is barely visible. The buildings are almost completely obliterated by the smoke from each of the ships in the East River and docked at the Brooklyn waterfront. In this watercolor, the smoke takes the role of the war and the buildings that make up the skyline symbolize normal everyday life. The smoke masks the buildings, although the buildings still do stand. The country was consumed with the war effort, much like the smoke consumes this painting, yet the buildings, and everyday life during the war, go on.[1]


In the center of the bottom of the painting, we see a small American flag hanging off of the back of one of the ships. The flag, although small, is clearly a main focus of the painting. In 1944, America had been fighting in World War II for several years. By including the flag in her painting, Dorothy makes a statement about her patriotism.

In this 1968 painting, we can clearly see the skyline changing. In the center of the watercolor there is the bones of a new building being constructed. This building is located at 111 Wall Street and it will house 24 floors. It will be in the international style architecture, made with a combination of glass, steel, and concrete.[2]


One thing is particularly interesting about this piece. The building at 111 Wall Street was finished being built in 1966. However, McEntee has dated her watercolor with the building at 111 Wall Street under construction in 1968. Perhaps she was painting from memory after the building was completed? Or maybe she had started a draft of the painting before 1966 and came back to complete it in 1968?


It is also possible that McEntee was attempting to make a deeper meaning. The Manhattan skyline continues to grow and grow with new buildings going up every year. Although the New York skyline is certainly iconic, it never remains the same and undergoes constant change.

In her 1967 painting, “Feathery Clouds” McEntee creates an image of the skyline during an overcast and rainy day. One can see the fog permeating the picturesque skyline in the watercolor from the blurred buildings and swirls of the clouds above.[3]

In her 1968 “Low Ceiling” watercolor, Dorothy McEntee perfectly displays the skyline on a dark and stormy day. The title of the painting impeccably captions the display; there is a dark masking fog covering the tops of the skyscrapers, a low ceiling that the tallest buildings manage to break through. The points of these skyscrapers puncture the dark ceiling above, further illustrating their magnitude and the contrasting height between the buildings.[4]

“Night in Port from Brooklyn Heights Window,” painted in 1968, portrays the image of the skyline from Brooklyn Heights at night. The sky above the buildings is black, however the buildings shine light onto the dark sky. The lights from the buildings can also be seen in the reflection on the water.[5]

This McEntee untitled watercolor piece stands out because of a singularly noticeable and distinctive characteristic. In the top left hand corner of the painting, there is a large 5-pointed shining star. The light from this star shines down onto the buildings, giving them some color during the dark night. There are beams coming off of the star that further define its presence. The question is, why would Dorothy McEntee want to add such a comically stereotypical star to her otherwise realistic painting? None of her other images contain anything unrealistic. Perhaps Dorothy McEntee wanted to emphasize the height and magnitude of these buildings, several of which reach the height of the star. In fact, some of the skyscrapers surpass the star by climbing even higher into the sky. This may point to the idea of human construction overcoming nature. The buildings are so high and mighty that they surpass even the stars.


The star also may be a biblical reference, referring to the star of Bethlehem.[6] McEntee may be pointing to the treasure that New York City holds in its art. Or perhaps she is marking the treasure that is the New York skyline or that is New York City as a whole. Maybe it was merely a painting she did to celebrate the Christmas holiday.

The perspective in this 1949 watercolor “Tugboats (from Lizzy’s Window)” is much further down than most of the other McEntee paintings. The skyline is shown in the right corner, as opposed to the center focal point. In this watercolor, the focal points are the Brooklyn waterfront and a larger boat out in the East River. The bottom portion the painting focuses on a pier of the Brooklyn waterfront, with the image of a warehouse and railroad cars at the water’s edge.[7]

Dorothy McEntee’s watercolor entitled “Chess Castle Tugboat offers a glimpse of the skyline out of McEntee’s own living room bay window at 57 Montague Street in Brooklyn Heights. Painted in 1983 after she retired, it is the last watercolor she painted of the skyline that we know of. This painting displays the Twin Towers of the World Trade Center is all their glory. They dominate over the skyline.[8]

In this 1944 watercolor, entitled “Rotting Pier”, McEntee displays a decaying pier along the Brooklyn waterfront. The pier represents what the waterfront was and what it is in the process of becoming. From McEntee’s painting, it appears that traffic along the waterfront is may be beginning to slow as tunnels start to be created and New Yorkers become less and less reliant on traveling by boat.


Today, we still see images of the rotting docks in the skyline that point to the past.[9]

McEntee’s painting “Mr. Pierpont’s Ghost” was painted in 1942. In the watercolor, we see a building being built along the Brooklyn waterfront. Looming behind this building being constructed is the New York skyline. One can tell it’s an earlier skyline of the city because of the massive gaps between each of the buildings. Both the buildings that compose the Lower Manhattan skyline and the buildings at the Brooklyn waterfront stand in sharp contrast to McEntee’s deep blue sky in the watercolor. [10]


In her title, McEntee speaks of “Mr. Pierpont.” Henry Pierpont played a significant role in the planning of Brooklyn as a city.[11] The painting displays Brooklyn being built up and, from McEntee’s title, one can assume that the ghost of Mr. Pierpont would be smiling down at his flourishing city.

In one of her paintings titled “Bathsheba in Brooklyn” from 1949, Dorothy McEntee portrays something completely unusual both for her and for the waterfront: a sun bathing woman dressed in nothing but a bikini resting on one of the docks in Brooklyn.[12] Especially considering the conservative mindset of the 1940s, it is fascinating that Dorothy would chose to depict such a scene.


This watercolor also displays how the people of Brooklyn have become so accustomed with the scenery around them that they are able to lay back and relax because they are accustomed with the waterfront and its corresponding machinery. This woman isn’t made uncomfortable by the massive boats or the water underneath and surrounding the pier she is sleeping on.

This 1968 watercolor entitled “The Lady Watches” is a perfect example of how McEntee’s titles point towards what she is attempting to convey in paintings. In the painting, the Statue of Liberty is quite small, appearing in the upper left corner. Viewers may not have paid much notice to her, however, McEntee’s title conveys her importance. Powerful Lady Liberty watches over the East River, much like a mother watches over her young.

“Arrival #3” was painted by McEntee with the other two “Arrival” watercolors in 1968. The painting displays large, impressionistic, cumulonimbus clouds above the skyline. These puffy clouds stand in stark contrast to the boxy dark buildings of the skyline below. The arrival in each of the paintings appears to be a large boat in the East River. In the bottom right of the painting, we see the outline of three of the warehouses on the Brooklyn waterfront.[13]

Painted in 1968, “Arrival #2” is a part of a series of paintings entitled “Arrival” by McEntee. The watercolor displays large, impressionistic, cumulonimbus clouds above the skyline. The arrival in each of the paintings appears to be a large boat in the East River. In the bottom right of the painting, we see the outline of three of the warehouses on the Brooklyn waterfront. “Arrival #2” is different that both “Arrival #3” and “Arrival #1” in that the clouds contain a peach pink underside.[14]

“Arrival #1”, like “Arrival #2” and “Arrival #3” was painted by McEntee in 1968. The painting displays large, impressionistic, cumulonimbus clouds above the skyline. The arrival in each of the paintings appears to be a large boat in the East River. In the bottom right of the painting, we see the outline of three of the warehouses on the Brooklyn waterfront. “Arrival #1” differs from “Arrival #3” and “Arrival #2” in that there is a thick black line outlining the largest cloud in the sky.[15]

McEntee’s painting entitled, NY: A Winter Playground or NY Winter Sport”, was painted in 1982 from her apartment window or the roof of her building. Viewers can see the rooftop of the building in front of McEntee’s building in Brooklyn Heights. The rooftop is easily distinguishable from its smokestacks.


The watercolor also displays people relaxing on the Brooklyn Promenade with their pet dogs.[16]

This 1949 McEntee painting entitled “Brooklyn Bridge,” displays how the Brooklyn Bridge cuts through the city of Brooklyn.[17]

McEntee painted this watercolor entitled “Curtain Going Up” in 1949. In the watercolor, the clouds act as the curtain rising up over the skyline.[18]

Dorothy McEntee’s skyline watercolor entitled “Workaday River” was painted in 1962. McEntee’s title clearly points to what she is attempting to convey in this painting. In “Workaday River”, she questions how many jobs are held in her view of the skyline. Thousands if not millions of New Yorkers work in the large buildings, which compose the actual skyline, and in the river and Brooklyn waterfront, which create the frame for the skyline. All of those people are a part of the view of one person.[19]

In her 1961 painting, “Entrance to the Esplanade,” Dorothy McEntee captures a single person walking along the Brooklyn Promenade. Behind the person, one can see the Brooklyn waterfront, complete with piers, warehouses, cranes, and a large ship in the harbor.[20]

In Dorothy McEntee’s 1968 watercolor entitled “Metamorphosis: Manhattan (From Brooklyn Heights Window)”[21] we see the skyline changing, specifically at the tip of Manhattan near the Staten Island Ferry dock. McEntee depicts a building under construction. We see a skeleton of a short fat building that will eventually become Four New York Plaza. Finished in 1968, this building will go on to become a 21-story high-rise built in the international style.[22]

In McEntee’s watercolor from 1973, entitled “Late Light,”[23] one can see the entire New York Plaza completed. The One New York Plaza building and the Two New York Plaza building block many of the buildings that used to dominate this section of the skyline.[24]

Dorothy McEntee’s painting “Tug Leaving” was painted in 1967. In the painting, the skyline appears to become more of a block of buildings as opposed to her earlier images of the skyline, which depicted much more space and sky in between each of the buildings of the skyline.[25]

McEntee’s “Smoke Trail & Snow” watercolor, painted in 1962, is unique amoung her skyline paintings in the fact that snow appears on the actual skyline. The snow is not overwhelming and just forms a white line across the tops of the buildings in the skyline and along the Manhattan piers.[26]

Dorothy McEntee’s painting “Smoke Plumes” was painted in 1980. In the watercolor, it appears that she may be pointing towards the pollution the skyline brings about from its massive buildings.[27]

One of McEntee’s later works ,“A Man, A Bird, and a Boat”, was painted in 1978. It is fascinating that of all the “things” that appear in this painting, Dorothy choses to ignore the skyline in her title. She does not entitle the watercolor, “A Man, A Bird, a Boat, and the Skyline” but rather “A Man, A Bird, and a Boat”, completely disregarding the massive skyline that dominates the scene.[28] This tells us that the skyline has become part of the background landscape of everyday life to McEntee. Because it has become so commonplace, it doesn’t even need to be named in her title like the bird, boat, and man do.

This 1979 watercolor entitled “Daphne Oak” does not show the water front or the skyline. “Daphne Oak” instead focuses on the view of the promenade from Dorothy’s apartment. In this image, we see a snow covered promenade with spectators walking along. Some stand by the edge of the promenade, presumably looking at the same skyline that McEntee focuses on in her watercolors.


“Daphne Oak” is distinctive among Dorothy McEntee’s paintings because it is clearly painted from her apartment window. But the most unique aspect of “Daphne Oak” is that McEntee shows the perspective of the scene not from a window pane as she does in two of her other works, but by depicting ice sticking to her window. The technique that McEntee uses to create the ice sticking on the window is very impressive in a watercolor.[29]

McEntee’s “Pink Light #III” was painted between 1967-1968. In the watercolor, we see a pink sunset over the skyline. Light pours out of the windows of the buildings, creating a beautiful scene that is then reflected in the East River.[30]

“Skyline Wall Street” by Dorothy McEntee is dated 1967-1977. The watercolor depicts the Lower Manhattan Skyline framed by a dark green sky and the East River.[31]

“Empire State Bridge” is among the three watercolors that Dorothy McEntee clearly drew from her apartment windows at The Breuklyn. In this 1975 watercolor, we see the frame of the window swung out to the left, leaving an uninterrupted view of the edge of the skyline. Presumably, this watercolor was drawn from McEntee’s bathroom window, as it is the only window in her apartment with a single pane of glass as opposed to a window with multiple panes, such as the bay window in her living room or the 3-paned window in her kitchen. Initially, the painting only seems to feature the Staten Island Ferry harbor and a pretty pink sky at sunset with a tugboat and a warehouse prominent at the Brooklyn waterfront. But then, as we look closer, we see the image of the skyline reflected in the glass of the window. We can clearly make out the Wollworth building and 111 Wall Street, along with some other buildings that are not nearly as descript.[32]

This 1938 watercolor is unique among Dorothy’s paintings for several reasons. First off all, it is the only watercolor that we still have access to that displays the skyline from the Brooklyn Bridge. It is not only obvious that McEntee is painting from the bridge from the location of the buildings, but she painted the wire cables of the bridge across the painting. The cables run both vertically and diagonally crossing over each other, creating a sort of net. These cables section off the watercolor, allowing viewers to focus on individual portions of the skyline separated from the entirety of the skyline. The lines that the vertical cables create mimic the vertical lines created by the buildings in the skyline.


“Thru the Cables” was also the watercolor that Dorothy exhibited at the 1940 World’s Fair.[33]

In this painting, we see the East River filled with tugboats and other ships carrying people and goods. Unlike the majority of Dorothy McEntee's paintings, neither the skyline, nor the Brooklyn waterfront, is the focus of this watercolor. Instead, it is the ships that dominate the scene. The amount of ships that McEntee features in "Busy Harbor" create a feeling of busyness and crowding. The pluming smoke coming from each of the ships further illustrates this emotion.[34]

McEntee’s “River Plate Wharf”, painted in 1942, focuses on the Brooklyn waterfront. On the water’s edge we see a yellow building with a gray roof with a sign labeling the building as “River Plate.” We see multitudes of people walking on the pier, as if they are walking home from work. There are many other small buildings along the waterfront and a tugboat crossing the East River.


There is also an image of the skyline in background, although many of the buildings are blotted out and unidentifiable, as if they are concealed in a mask of fog.[35]

[1] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.45.

[2] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.37.

[3] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.28.

[4] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.30.

[5] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.17.

[6] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.13.

[7] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.27.

[8] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.26.

[9] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.3.

[10] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.5.

[11] “A Short History of Brooklyn Heights,” Brooklyn Heights Association, 2014, http://www.thebha.org/about-the-neighborhood/history/.

[12] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M1991.36.7.

[13] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.18.

[14] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.19.

[15] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.20.

[16] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.21.

[17] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.22.

[18] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.23.

[19] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.24.

[20] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.25.

[21] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.29.

[22] “New York City Skyscraper Map,” Skyscraper Source Media, 2014, http://skyscraperpage.com/cities/maps/?cityID=8.

[23] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.31.

[24] “New York City Skyscraper Map,” Skyscraper Source Media, 2014, http://skyscraperpage.com/cities/maps/?cityID=8.

[25] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.32.

[26] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.33.

[27] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.34.

[28] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.36.

[29] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.39.

[30] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.40.

[31] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980), M.1991.36.29.

[32] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.48.

[33] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.49.

[34] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.50.

[35] "Dorothy McEntee: Realist in Watercolor," (Accession files for Dorothy Layng McEntee paintings, Brooklyn Historical Society, 1980),M1991.36.51.