Portrait of Nathan Jay Jaffee

Meet the 74 Most Famous Paintings by Nathan Jay Jaffee

Updated October 2026 · ranked by our popularity score (searches, visits and orders for each work) · 74 works by Nathan Jay Jaffee in our catalogue

In short

If you know one Nathan Jay Jaffee painting, it's probably Fools of Desire (1980). Canal Street (Ace) (1980) and Two Men in Subway (1979) round out the three pieces people recognise right away. Our catalogue has 74 works by Nathan Jay Jaffee. Below are the 74 people know best, each with its year, where to find it and what makes it special.

1921 – 1999 Contemporary realism Most works: Harvard Art Museums

Start here: the top 10 Nathan Jay Jaffee paintings

More Nathan Jay Jaffee favourites, 11 to 74

11Clouds and Landscape 16 (1990) by Nathan Jay JaffeeClouds and Landscape 161990 12Man Blinding Himself By Staring at the Sun (1991) by Nathan Jay JaffeeMan Blinding Himself By Staring at the Sun1991 13Bryant Park (1953) by Nathan Jay JaffeeBryant Park1953 14Two Men (1977) by Nathan Jay JaffeeTwo Men1977 15Man Walking and Tree (1976) by Nathan Jay JaffeeMan Walking and Tree1976 16Man and Woman with Shadows (1974) by Nathan Jay JaffeeMan and Woman with Shadows1974 17Anti Vietnam March 1 (1977) by Nathan Jay JaffeeAnti Vietnam March 11977 18Man with Bowler (1980) by Nathan Jay JaffeeMan with Bowler1980 19Man in Frame (1980) by Nathan Jay JaffeeMan in Frame1980 20Self Portrait (1979) by Nathan Jay JaffeeSelf Portrait1979 21Industrial Building Lobby (1980) by Nathan Jay JaffeeIndustrial Building Lobby1980 22Downtown, Brooklyn (1980) by Nathan Jay JaffeeDowntown, Brooklyn1980 23Pillars in Sunlight (1980) by Nathan Jay JaffeePillars in Sunlight1980 24Building Repair (1979) by Nathan Jay JaffeeBuilding Repair1979 25Girl on Skates (1980) by Nathan Jay JaffeeGirl on Skates1980 26Sun Park 2 (1980) by Nathan Jay JaffeeSun Park 21980 27IRT Train Detail 2 (1979) by Nathan Jay JaffeeIRT Train Detail 21979 · Harvard Art Museums 28Man with Straw Hat (1980) by Nathan Jay JaffeeMan with Straw Hat1980 29Merry Go Round (1979) by Nathan Jay JaffeeMerry Go Round1979 30House and Tree (1978) by Nathan Jay JaffeeHouse and Tree1978 31Strange Fruit (1979) by Nathan Jay JaffeeStrange Fruit1979 32Under the El (Handball Players) (1980) by Nathan Jay JaffeeUnder the El (Handball Players)1980 33Wall Street (1980) by Nathan Jay JaffeeWall Street1980 34Bagpipe Player (1980) by Nathan Jay JaffeeBagpipe Player1980 35Novelty Shop (1979) by Nathan Jay JaffeeNovelty Shop1979 36From the Pompidou (1983) by Nathan Jay JaffeeFrom the Pompidou1983 37Synagogue (1981) by Nathan Jay JaffeeSynagogue1981 38Looking at Sand Sculpture (1981) by Nathan Jay JaffeeLooking at Sand Sculpture1981 39Two Artists Under the Brooklyn Bridge (1983) by Nathan Jay JaffeeTwo Artists Under the Brooklyn Bridge1983 40Woman with Broom (1981) by Nathan Jay JaffeeWoman with Broom1981 41Tire Store (1981) by Nathan Jay JaffeeTire Store1981 42Old Straw Hat (1981) by Nathan Jay JaffeeOld Straw Hat1981 43If You Believe in Credit (1981) by Nathan Jay JaffeeIf You Believe in Credit1981 44At the Minster (1982) by Nathan Jay JaffeeAt the Minster1982 45Worth Street, Facing West (1981) by Nathan Jay JaffeeWorth Street, Facing West1981 46Hanger Sculpture (1986) by Nathan Jay JaffeeHanger Sculpture1986 47West Neck Beach (Two Figures) (1985) by Nathan Jay JaffeeWest Neck Beach (Two Figures)1985 48Coffee Shop (1987) by Nathan Jay JaffeeCoffee Shop1987 49Spectators, May Day Parade (1986) by Nathan Jay JaffeeSpectators, May Day Parade1986 50Overcoming Love (1985) by Nathan Jay JaffeeOvercoming Love1985 51Power Station (1986) by Nathan Jay JaffeePower Station1986 52Woman Looking Out Window (1989) by Nathan Jay JaffeeWoman Looking Out Window1989 53Sculpture with White Paint (1989) by Nathan Jay JaffeeSculpture with White Paint1989 54Clouds with Landscape 12 (1990) by Nathan Jay JaffeeClouds with Landscape 121990 55White Birches, Mohonk, New York (1988) by Nathan Jay JaffeeWhite Birches, Mohonk, New York1988 56Clouds with Landscape 11 (1990) by Nathan Jay JaffeeClouds with Landscape 111990 57Seaman Strike, Treasury Building, NYC (1990) by Nathan Jay JaffeeSeaman Strike, Treasury Building, NYC1990 58Group Picture (1989) by Nathan Jay JaffeeGroup Picture1989 59Oriole Baths (1989) by Nathan Jay JaffeeOriole Baths1989 60Foliage, Caumsett Park, Long Island (1989) by Nathan Jay JaffeeFoliage, Caumsett Park, Long Island1989 61Woman Under Movie Marquee (1989) by Nathan Jay JaffeeWoman Under Movie Marquee1989 62Clouds and Seascape 1 (1990) by Nathan Jay JaffeeClouds and Seascape 11990 63Baltimore Gunsmith (1989) by Nathan Jay JaffeeBaltimore Gunsmith1989 64House and Field (1990) by Nathan Jay JaffeeHouse and Field1990 65Clouds and Landscape 18 (1990) by Nathan Jay JaffeeClouds and Landscape 181990 66Shalom (1991) by Nathan Jay JaffeeShalom1991 67Share with Others (1991) by Nathan Jay JaffeeShare with Others1991 68Lloyd Harbor Pond, Frame 11 (1991) by Nathan Jay JaffeeLloyd Harbor Pond, Frame 111991 69Man Walking, Brooklyn Bridge (1991) by Nathan Jay JaffeeMan Walking, Brooklyn Bridge1991 70Clouds with Landscape 5 (1991) by Nathan Jay JaffeeClouds with Landscape 51991 71Spring 2 (1992) by Nathan Jay JaffeeSpring 21992 72Morning Scene (1992) by Nathan Jay JaffeeMorning Scene1992 73Wall Graffiti (1983) by Nathan Jay JaffeeWall Graffiti1983 74Ban the A Bomb (1989) by Nathan Jay JaffeeBan the A Bomb1989

Nathan Jay Jaffee's paintings, period by period

What Nathan Jay Jaffee painted most

The four subjects that come up most often in these pieces, each with its best-known example.

Where you can see Nathan Jay Jaffee's paintings

The museum that holds the most of the paintings on this page.

Museum City Works by Nathan Jay Jaffee Paintings from this list
Harvard Art Museums, CambridgeHarvard Art Museums Cambridge 1 IRT Train Detail 2

Nathan Jay Jaffee decade by decade: one standout piece each

Works per decade

Pick a decade to see its standout piece.

Your questions about Nathan Jay Jaffee's paintings

Which Nathan Jay Jaffee painting is the most famous?See the answer

Top of the list is Fools of Desire (1980). Right behind it: Canal Street (Ace) (1980) and Two Men in Subway (1979).

How old was Nathan Jay Jaffee when Fools of Desire was made?See the answer

59 years old. Nathan Jay Jaffee was born in 1921, and Fools of Desire dates from 1980.

What are the 10 best-known Nathan Jay Jaffee paintings?See the answer

Fools of Desire, Canal Street (Ace), Two Men in Subway, Horse and Wagon, Kishke King, Fight for Peace, Two Boys (Shoe Shine), Woman Reading Paper Under the El, Hazard 1 and Woolworth Building. You'll find the year and the museum of each in the list above.

How many paintings did Nathan Jay Jaffee create?See the answer

We have 74 works by Nathan Jay Jaffee in our catalogue, dated 1953 to 1992.

Where can you see Nathan Jay Jaffee's famous paintings?See the answer

You'll find most of them in Harvard Art Museums (Cambridge). The museum list above has the full breakdown.

When did Nathan Jay Jaffee paint the best-known pieces?See the answer

In 1980s, more than any other time: 43 of the 74 pieces on this page date from then, Fools of Desire among them.

Which famous Nathan Jay Jaffee paintings came first and last?See the answer

The earliest piece here is Bryant Park (1953); the most recent is Spring 2 (1992).

What subjects show up most in Nathan Jay Jaffee's paintings?See the answer

Black and white image (3), Black and white (3) and Social commentary (3), out of the 74 pieces on this page.

What art movement was Nathan Jay Jaffee part of?See the answer

Contemporary realism and Documentary photography, as you can see in the pieces on this page.

Getting to know Nathan Jay Jaffee

Nathan Jay Jaffee: A Chronicle of American Life

Nathan Jay Jaffee (1921-1999) wasn’t a name immediately recognized by the public, yet his photographs offer an intimate and remarkably honest portrait of mid-20th century America. More than simply documenting scenes, Jaffee possessed a keen eye for capturing the essence of everyday life – from bustling city streets to quiet rural landscapes, from political rallies to solitary moments of reflection. His work, often characterized by its understated elegance and subtle social commentary, reveals a deep understanding of human nature and a profound connection to the American spirit.

Born in Brooklyn, New York, into a family of Russian immigrants, Jaffee’s early life instilled in him a strong sense of independence and resilience. He began working as a typesetter at a young age, supporting himself through the challenging years of the Great Depression. This experience, coupled with his military service during World War II – earning a Bronze Star for valor – shaped his perspective and informed his artistic approach. Following the war, he enrolled in photography classes taught by Sid Grossman, a key figure in the influential Photo League, an organization dedicated to socially conscious documentary photography. Grossman’s guidance proved pivotal, introducing Jaffee to techniques of street photography and fostering a commitment to capturing authentic representations of urban life.

The Early Years: Brooklyn Streets and the Echoes of the Photo League

Jaffee's early work focused primarily on the streets of Brooklyn – a vibrant tapestry of immigrant communities, working-class neighborhoods, and burgeoning cultural scenes. He meticulously documented these environments, capturing the faces, gestures, and textures that defined daily life. His photographs weren’t grand pronouncements; instead, they were quiet observations—a solitary figure reading a newspaper, children playing in a stoop, the weathered facade of a tenement building. This approach echoes the ethos of the Photo League, though Jaffee ultimately forged his own distinct style, characterized by a sensitivity to light and composition that set him apart.

Crucially, Jaffee’s connection to the Photo League extended beyond mere instruction; it provided him with a framework for understanding photography as a tool for social engagement. He participated in exhibitions alongside other members of the league, contributing to a broader dialogue about the role of art in reflecting and shaping society. His early work was later compiled and published in 1976 under the title “N. Jay Jaffee: Photography 1947-1956,” solidifying his place within this important photographic movement.

Expanding Horizons: From Urban Landscapes to Social Commentary

As time progressed, Jaffee’s subject matter broadened beyond the confines of Brooklyn. He traveled extensively throughout the United States and Europe, documenting diverse landscapes and capturing scenes of political demonstrations and social movements. The rise of the Civil Rights Movement and the anti-war protests of the 1960s profoundly influenced his work, leading him to photograph rallies, marches, and gatherings where individuals voiced their concerns about injustice and peace.

His portraits became increasingly significant during this period. He photographed a diverse range of subjects – artists, intellectuals, activists, and ordinary people—capturing their personalities and conveying their stories with remarkable empathy. Notable among his portrait subjects were Yoko Ono, Pete Seeger, Isaac Bashevis Singer, and Stan Brodsky, reflecting his engagement with the cultural and intellectual currents of his time.

A Shift Towards Nature: Late Works and Enduring Legacy

In later years, Jaffee’s focus shifted towards nature photography. He moved to Lloyd Harbor, Long Island, where he found solace and inspiration in the landscapes surrounding him. His late works are characterized by a serene beauty and a contemplative mood—images of coastlines, fields, and forests that evoke a sense of timelessness and connection to the natural world.

Despite his relatively quiet career trajectory, Jaffee’s work has been recognized for its enduring quality and artistic merit. A major retrospective, “Inward Image: Photographs by N. Jay Jaffee,” was held at the Brooklyn Museum in 1981, followed by another significant exhibition in 1999 at the Heckscher Museum of Art, Long Island, shortly after his death. His photographs are now housed in numerous museums and institutions across the United States and abroad, testament to their lasting impact on American photography. Nathan Jay Jaffee’s legacy lies not in grand pronouncements or revolutionary styles, but in his quiet, observant eye—a window into the heart of America.