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Top 10 Antique Paintings Depicting Historic New York City

New York City is legendary—it’s no surprise it’s been the muse for countless artists. Painters and photographers have long been capturing the city’s vast urban sprawl into one, static image. Whether you’re a collector of vintage art, decorating your new home, or dreaming about life in New York City, here are some antique portrayals of the most impressive cityscape in the world.
Mark Rothko's "Subway"
Mark Rothko’s “Subway”
  • Jane Dickson, Hotel Girl, 1983. Jane Dickson’s Hotel Girl captures the duality of Times Square in the early ’80s—both its gritty underbelly and glamor. In 1981, Jane and her husband Charlie Ahearn moved into a loft overlooking Times Square. While working on the first-ever Spectacolor billboard, Jane painted a series of works, including Hotel Girl, during the period when Times Square was as notorious as it was iconic.
  • Theresa Bernstein, The Lunch Counter at S. Klein’s in Union Square in the 1930s, ca. 1930–39. Theresa Bernstein’s watercolor portrays the racially integrated lunch counter at S. Klein’s, a beloved New York City department store. For 65 years, S. Klein’s, located by Union Square, was a magnet for bargain hunters. According to an archival New York Times article, the Manhattan store (and others in Flushing, Queens, and Lake Success, Long Island) closed their doors in 1974 due to declining sales.
  • Mary Heilmann, Chinatown, 1976. Mary Heilmann’s Chinatown reflects her early experimentation with color theory and her integration into the New York art scene. After moving to New York City in 1968, the sculptor resided in a Chinatown loft and was deeply influenced by Josef Albers, considered one of the most influential 20th-century art educators in the United States.
  • Ilse Bing, New York, the Elevated, and Me, 1936. In 1936, German-Jewish photographer Ilse Bing was invited to solo-exhibit her work at the June Rhodes Gallery. During her two-month stay in New York City, she photographed the resilience and growth of the city in the post-Depression era. One of her standout images, New York, the Elevated, and Me, captures the Manhattan skyline from an elevated train station, framing the Chrysler Building.
  • Andy Warhol and John Palmer, Empire, 1965. Empire, a black-and-white silent art film by Andy Warhol, was shot from the 44th floor of the Time-Life Building. The film features eight hours and five minutes of slow-motion footage of the Empire State Building from a fixed perspective. Warhol sought to compare the cinematic experience to a statement on the passage of time. Empire is distributed by the Museum of Modern Art’s (MoMA) Circulating Film and Video Library.
  • Berenice Abbott, New York at Night, ca. 1933. Berenice Abbott was best known for her portraits of New York City, which she viewed as art itself. New York at Night—one of the many photographs from a project recording New York’s 1920s building boom—is a birds-eye view of the West Side looking north.
  • Diego Rivera, Frozen Assets, 1931. After arriving in New York City from Mexico City in 1931, Diego Rivera became fascinated by Manhattan’s distinctive vertical architecture. Frozen Assets, which was created for the Museum of Modern Art, is divided into three sections: the skyline, the Municipal Pier on 25th Street, and a Wall Street bank vault. It was a critique of the city’s economic stratification during the Great Depression.
  • William Chappel, Manhattan, ca. 1808. Travel back to early 19th-century New York; an era when streets and sidewalks were lit up by whale oil and lamp lights each night. This oil painting series is by William Chappel, a tinsmith and amateur painter who lived at 165 Bowery.
  • Mark Rothko, Untitled (The Subway), 1937. This painting is part of Rothko’s 1930s Subway Series, completed after the first line of New York City’s Independent Subway System (IND) opened in 1932. The Subway paintings capture Rothko’s love-hate relationship with urban life and have since found a home in the Elie and Sarah Hirschfeld collection.
Diego Rivera, "Frozen Assets"– a critique of the NYC's economic stratification during the Great Depression.
Diego Rivera, “Frozen Assets”– a critique of the NYC’s economic stratification during the Great Depression.
map of New York City