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Painting Pretty Penny

“There’s a man outside making a picture,” exclaimed Helen Hayes’ daughter Mary while looking out the window of their home, Pretty Penny, on North Broadway in November 1939. Mary espied Edward Hopper seated in the front yard wearing his trademark fedora and overcoat sketching Pretty Penny. Mary’s father, Charlie MacArthur, commissioned an oil painting of the house by Hopper as a gift for his wife, Helen Hays, a two-time Oscar winner and one of the few people to have won the EGOT ( an Emmy, Grammy, Oscar, and Tony award).

Hellen Hayes, Mary, and Charles MacArthur

That day, Edward Hopper took a bus from his Washington Square apartment to make his first sketches of the house for the only commission he ever accepted. The work made him very grumpy despite the hefty $2,500 commission. Aside from his days at art school, it was to be the only time that anyone told Hopper what to paint.

Pretty Penny by Edward Hopper, 1939. Courtesy of the Smith College of Art Museum.
A view of Pretty Penny in 2017, similar in perspective to Hopper’s painting, shows how accurately Hopper incorporated architectural details into his final work,

The Italianate house at 235 N. Broadway that Became Pretty Penny

Pretty Penny has a lengthy lineage. Eli Gurnee, a Nyack merchant and landowner, built the Italianate-style house, with its distinctive central rooftop belvedere, around 1857. In 1872, local architect Horace Greeley Knapp completed an expansion and remodeling of the house. The interior is theatrical; there are unusual details, including a 2-story glass-topped entry way on the north side.

Behind the house, overlooking the Hudson River, a series of terraces step down to the river. Hayes’ rose garden still thrives along with a terraced fountain and swimming pool. The lower tennis court and boat dock are long gone, replaced with a contemporary river front building. Hayes installed a brick wall along the sidewalk for privacy. Later, Rosie O’Donnell added tall evergreens to obscure the face of the house.

Photo of a 1971 Nyack Garden Club event in the Rose Garden. Courtesy of the Nyack Library.

According to common legend, Hayes exclaimed that the house cost them a pretty penny, and the name stuck. Artist Bennard Perlman offered a different suggestion, that “the name does not refer to the $1,500 Depression-era price they paid for the house, but rather to a radio series, ‘The New Penny,’ in which Hayes played a part.” “All the money I made on that show went into the house and to buy the painting,” Hayes once confessed.

Commissioning the Painting

The year 1939 was a lean time for Hopper. When he got the MacArthur commission, he hadn’t painted anything for months. His art dealer, Frank Rehn, told Hopper that MacArthur chose him because Hopper grew up just down the street. Both Rehn and Jo, Hopper’s wife, encouraged him to take the commission; the money was good.

Hopper self-portrait circa 1925-1920. Courtesy of the Whitney Museum of Modern Art

Hopper resisted for all kinds of reasons. After viewing the house on November 3, he declared it was impossible to paint because it was too hard to simplify. According to Jo’s diary, “the back (of the house) was too cut up with staircases coming down from 2 sides & much doing in the grounds: swimming pool, tennis court and boat landing.” During his first visit with MacArthur and Hayes on November 3, Hopper told them he didn’t want to paint the house. Hayes claimed Hopper said that “it does nothing for me…there is no light and there’s no air that I can find for the house.” Jo found his behavior embarrassing, but she convinced Edward to get started before it got any colder.

Contemporary view of the river side of Pretty Penny that Hopper found “too busy” to make a good painting.

Painting Pretty Penny

Hopper did most of his paintings in his studio from detailed sketches made on site. He made his first on-site sketches of Pretty Penny on November 8. Hopper returned with Jo the next day to make a sketch of the front of the house. He also made sketches of details of the façade. On the 10th, he made another sketch that included a tree branch dangling from the top left. He incorporated it into the final work.


Hopper stretched the canvas on November 16, making it small (40″ x 28″). The canvas framed the house exactly without much foreground or sky. He approached the work as he had done with his earlier commercial illustration work, transferring the sketch mechanically to the canvas. On November 24, Edward and Jo came back to Nyack to check the color of the house and note more details. To complete the work, Hopper got up early in the morning so as to paint in the dim December light of his studio. By December 11, he finished the clapboards. He worked steadily until he finished on the 16th.

Final sketch for Hopper’s painting. Courtesy of the Whitney Museum of Modern Art.

On December 17, Edward was cussing out his wife Jo, Helen Hayes, and his dealer because they requested that he paint in Hayes’ daughter and their French poodle. He did not give in. On December 21, he took the painting in to Rehn with the title Pretty Penny. When MacArthur called to say how pleased he was, Hopper was gruff. Jo had hoped to invite MacArthur and Hayes down to their studio but Edward was having none of it. Hayes hung the painting in the downstairs parlor of Pretty Penny.

Helen Hayes in her parlor with Hopper’s painting on the wall. Courtesy of the Nyack Library.

Pretty Penny Today

The painting appeared in exhibits at the Whitney and the Chicago Art Institute during Hopper’s lifetime. In 1964, Hayes donated the painting to the Smith College Museum of Art, which had awarded Hayes an honorary degree in 1940. The house has gone through several owners over the years including Rosie O’Donnell, who started the authentic restoration work that was completed by later owners.


Mike Hays is a 38-year resident of the Nyacks. He worked for McGraw-Hill Education in New York City for many years. Hays serves as President of the Historical Society of the Nyacks, and Vice-President of the Edward Hopper House Museum & Study Center. Married to Bernie Richey, he enjoys cycling and winters in Florida. You can follow him on Instagram as UpperNyackMike.


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