The 50 Greatest American Paintings

Is there such a thing as American painting? Yes, whether Hopper or Hicks, landscapes or lovers, it is weird and wonderful.

There are some conditions though. For example, American painting has always been influenced by art made in other parts of the world. Good American painting borrows from art history and either imparts a lesson or tries to effect social change. Great American painting does all of this and makes you feel something too.

These are, in no particular order, the 50 American paintings everyone should know.

The 50 Greatest American Paintings.

Written by @debyrd.

Follow @complex_art on Twitter.

Painter: Gilbert Stuart

Year: 1796

Stuart's painting is the exemplar for Washington's portrait on the dollar bill. It is thus arguably the most reproduced American painting of all time. Stuart was also concerned with the dollar. Recognizing the appeal of his Athenaeum portrait of Washington, he chose not to finish it; instead, he devoted his time to making as many copies of it as possible. Dollar, dollar bill y'all!

Painter: Emanuel Gottlieb Leutze

Year: 1851

This depiction of George Washington's perilous Revolutionary War crossing before the Battle of Trenton might be the most famous American painting of all time. It is meant to be seen with Wagner's Ride of the Valkyrie playing in the background.

Painter: Robert H. Colescott

Year: 1975

Satire is the name of Colescott's game. His work constantly deals with issues of racial representation and history by recasting well-known historical figures as African-Americans in familiar Western paintings. In this painting, George Washington, Revolutionary War general and first U.S. president becomes George Washington Carver, the black scientist and inventor.

Painter: Jasper Johns

Year: 1958

Here, Johns manages to divest the flag of much of its symbolic meaning. Instead he forces the viewer to focus on the richly painted surfaces and depth created by stacking three canvases on top of each other.

Painter: James Rosenquist

Year: 1960-61 and 1964

A close-up of John F. Kennedy's face, a woman's hands holding a slice of cake, and a portion of a Chevrolet, somehow combine and work well as a composition. Rosenquist explained the juxtaposition's logic: “The face was from Kennedy's campaign poster. I was very interested at that time in people who advertised themselves. What did they put on an advertisement of themselves? So that was his face. And his promise was half a Chevrolet and a piece of stale cake.”

Painter: Shepard Fairey

Year: 2008

Known to many of us as the poster plastered everywhere in support of now-President Barack Obama, this image began life as a 60” x 44” collage in Fairey's studio. OBEY.

Painter: Irina Rozeal Brown

Year: 2003

Twelve different colors are used to create Brown’s hybrid Afro-Asiatic figures. These mash-ups explore the intersections between Japan's ganguro culture and black American hip-hop and fashion. Brown isn’t just a visual artist, she is a DJ too and her paintings thrum with the beat of complexity of identity.

Painter: Martin Johnson Heade

Year: ca. 1870-1880

Heade masterfully negotiates representations of the background with close-up views of the money shot, err, let me try that again. Heade paints the natural habitats of exotic flora and fauna with a particular focus on the interrelationship of all God's creatures. In this painting, he depicts the moment shortly before consummation, prior to the hummingbird's encounter with the orchid.

Painter: Benjamin West

Year: 1770

The death of British General James Wolfe during the Battle of Quebec of the Seven Years War is figured by West as if it is Christ-like. In this neo-Lamentation scene, Wolfe is surrounded during his last moments. The scene is given a uniquely American cast by the figure of the kneeling Native American who is seemingly lost in deep thought. West's incredible history painting was criticized at the time for rendering the subjects in contemporary dress. Before West's painting, classical attire was thought to have been the only appropriate way to memorialize the event.

Painter: Kerry James Marshall

Year: 1994

Marshall takes on our American appetites, whether love of amusement parks, like California's Great America, or our (former) appetite for slavery. The National Gallery's announcement of their acquisition of Marshall's painting interprets it thus: “In Great America [Marshall] re-imagines a boat ride through the haunted tunnel of an amusement park as the Middle Passage of slaves from Africa to the New World. What might in other hands be a work of heavy irony becomes instead a delicate interweaving of the histories of painting and race.”

Painter: probably John Rose

Year: 1785-1790

For many years, scholars considered The Old Plantation to be the most important depiction of life on the plantation. They assumed that the painter must have had intimate, and unprecedented access to a slave community to have so carefully rendered slaves dancing the pat juba to music played on African-inflected instruments; some scholars went so far to suggest that he may have been even been a slave. Nope. Recent scholarship suggests that John Rose, a South Carolina rice planter, enslaved and painted the people depicted in this watercolor. Plantations were complex geopolitical entities.

Painter: Chuck Close

Year: c.2000-1

Close's large canvasses are incredibly detailed, forcing the viewer to combine small geometric details into one coherent image. Many have wondered if he uses computers to achieve the pixilated effect of his paintings. Nope. Close takes photographs of his subjects and then grids the photos and canvas to be painted.

Painter: Charles Wilson Peale

Year: 1822

From the carefully rendered turkey to the precisely administered cages replete with American fauna, Peale argues that art is the accurate transcription of observable facts. Too bad his upraised arm seems to have no connection to his shoulder.

Painter: Edward Hicks

Year: ca. 1825-30

The Quaker preacher, Hicks painted 61 different version of this composition. He believed that his paintings could impart important religious lessons. Under the guidance of Quakers, America is Eden where even the lion and ox peacefully co-exist.

Painter: John Singleton Copley

Year: 1778

Watson and the Shark was inspired by an event that took place in the harbor, Havana, Cuba. In 1749, fourteen-year-old Brook Watson was attacked by a shark while swimming in the harbor. His brave shipmates came to his rescue. Copley masterfully orchestrates all of the elements of the turbulent scene for maximum effect. Could Copley have picked a more dramatic moment to depict?

Painter: George Caleb Bingham

Year: 1846

Riverboat men on the Mississippi are the subjects of this painting. The boat holds little cargo suggesting that it is headed back up the Mississippi River. The men are free to engage in leisure activities as the central figure of this triangular composition dances to a tune we cannot hear.

Painter: John Smibert

Year: ca.1729-39

George Berkeley left London in 1729 to found a college in Bermuda; he and his entourage had their portrait made to commemorate their passage. The resulting painting is a conversation piece: Berkeley manages to simultaneously be well integrated in the group and set-off as a visionary. He looks heavenward to receive a message, which transmitted by him through the zigzag carpet pattern to his amanuensis on the viewer's right. It is like a divine game of telephone; My telephone, m-m-my telephone.

Painter: Henry F. Darby

Year: 1845

The hyper-real appearance of the sitters in this painting might be an indication of the pressures of early photography on the practice of painting. Darby was only seventeen when he made this painting of Reverend Atwood and his family. The sitters' pious appearance – they read five bibles – is juxtaposed against the fashionable furnishings and lush textiles that surround them.

Painter: Samuel F.B. Morse

Year: 1831-33

Morse faithfully transcribed what he believed to be the best paintings at the Louvre before transporting it back to the United States for display. He hoped that this painting would expose Americans to the best of European painting. The exhibition of Morse's massive painting was a flop. Today, Morse is best remembered for his invention of the telegraph and Morse code, not his paintings.

Painter: Asher Brown Durand

Year: 1849

Spirits was Durand's tribute to his dear and departed friend Thomas Cole. Durand created the perfect composite view of Cole's favorite sites, Kaaterskill Falls and the Catskill Cove. With his paintbrush Cole points to the great beyond, his final destination, as his friend William Cullen Bryant looks on. This painting was famously purchased from the New York Public Library as a different sort of tribute for the Crystal Bridges Museum in Bentonville, Arkansas.

Painter: Winslow Homer

Year: 1865

In an evocation of the Grim Reaper this Civil War veteran, his jacket and canteen discarded in the foreground, reaps golden wheat in a field. The scythe is strapped to the veteran in the way that his gun would have been during wartime. The viewer is denied the opportunity to see the veteran's face as he cuts down wheat in its prime; it only enhances the somber undertones of the painting.

Painter: Thomas Eakins

Year: 1875

This most “powerful, horrible, and fascinating” painting features a self-portrait of Eakins as the seated figure who scribbles with a writing implement that is as much scalpel as it is pen. It is based on a surgery led by Dr. Gross on the cancerous femur of a young man witnessed by Eakins. The painting was rejected for the art exhibition of the Centennial Exposition of 1876; it was relegated to ornament in the U.S. Army Hospital display.

Painter: Richard Philips

Year: 1998

Gossip Girl aficionados will recognize this painting from the Van der Woodsen apartment. Contrary to popular belief, the woman in the painting is not Blair (Leighton Meester) but inspired by a 1960s fashion advertisement.

Painter: Andrew Newell Wyeth

Year: 1948

Perhaps because it has been misunderstood as a depiction of teenage angst, for decades Christina's World was a dorm room poster staple. The woman actually depicted in the painting is Christina Olson, a woman who was paralyzed from the waist down as a result of a degenerative disease. Wyeth imbues the scene with emotion -- even for the viewer who is unaware of Olson's plight -- through the taut, yet invisible line stretching between her head and the peak of the house. Christina's destination seems impossibly far away.

Painter: John Singer Sargent

Year: 1884

Scandal! When this painting was exhibited at the Paris Salon of 1884, one strap of the subject's gown had fallen down her shoulder. Viewers were titillated and horrified. Madame X's mother demanded that the painting be taken down. Sargent refused on the grounds that he had painted her as she was dressed. He later repainted the strap to make it look more secure.

Painter: Anonymous

Year: c.1671-74

I don't know about you, but when I think Puritan I do not think about red and blacks ribbons and jewelry. Perhaps it is the contrast between the highly ornamented clothing of Elizabeth and her baby, Mary and their otherwise pious appearance that give this picture such a haunting feeling.

Painter: James Abbott McNeill Whistler

Year: 1871

This painting is so much more than a Mr. Bean plot point or an Arrested Development episode title. Alternatively referred to as an American icon or the “American Mona Lisa,” it is an emblem of motherhood and family values. Eschewing any sentimental value, Whistler pawned this painting shortly after creating it, and it eventually ended up in the Musée d'Orsay, Paris.

Painter: Henry Ossawa Tanner

Year: 1897

Tanner knew Whistler's painting and sought to pay homage to his mother in the same manner. He elevates the depiction of his own mother by humanizing her through gesture: one hand rests on her cheek; the other is dropped in her lap. The contemplative atmosphere is enhanced in the cool, moody palette.

Painter: Frederick Remington

Year: ca. 1908

This is the only nocturne to make the list. It is hard to pick out which element makes this painting feel so haunting. Maybe it is the way that the swath of burned grass separates the viewer from the picture, or the spooky look of the faces lit from below. I guess it doesn't matter what it is, because This. Picture.is.Disturbing.

Painter: Ernie Barnes

Year: ca. 1972

Ohhh, you thought JJ from Good Times painted this? No. Ernie Barnes AKA the NFL's 1960 10th draft pick did. He drew on his southern childhood and athletic experience to render fluid bodies in a style that is more mannerist than “Dy-no-mite!”

Painter: George Bellows

Year: 1909

Bellows was a mostly-pro baseball player –turned artist. As a result, he is especially attentive to the boxers/stags who lock horns in the ring. The gritty, dirty vulgarity of the fight is echoed in the audience, especially the figure on the far side of the ring who seems as violent as the event he watches.

Painter: Joseph Stella

Year: 1919-1920

Although Stella did not faithfully reproduce the bridge, his deft composition contains the bridge's most striking elements, including pedestrian walkways, Gothic arches, and the thicket of wires and cables. The hellish-red at the base of the painting is juxtaposed against the heavenly-blue that is the focus of the composition. Stella's painting is affective, and more evocative than a literal transcription of the bridge would be.

Painter: John Marin

Year: 1920

Marin famously painted New England landscape scenes and made even the most familiar views abstract. Here, even the city is made abstract; his depiction of the Woolworth building veers dangerously toward total abstraction. The building teeters ominously over us. Marin's roughly handles the surface: he dryly washes pigment and even scratches up of the paper's surface. Marin demonstrates that watercolor can be a modernist medium.

Painter: Grant Wood

Year: 1930

Yes, I know you've seen this painting before; but have you truly looked at it? If so, you would see that the painting is rigorously organized. The pitchfork in the man's hand is mirrored by a similar pattern in the stitching of his overalls. The stripes of his shirt are echoed in the boards of the house and barn behind him. The woman is tied into the composition through the pattern of the circles on her shirt, which rhyme with the spectacles on the man's face. In the ultimate rhyming pattern, the pair is rendered in a stiff manner, which ultimately resounds with the very surface it is painted on: a board.

Painter: Georgia O'Keeffe

Year: 1930

Skyscrapers, skulls or *ahem* flowers, O'Keeffe used the same technique to picture them all. She enlarges the subject to the edges of the frame, resulting in a fully frontal, oversized depiction. Anything O'Keeffe thus captures takes on a totemic quality: it is to be worshipped.

Painter: Edward Hopper

Year: 1942

Strangely enough, for a painting dripping with feelings of loneliness and estrangement it keeps pretty good company. Blade Runner's look was inspired by it. Wim Wenders famously recreated this scene for a film within a film in the History of Violence. The Simpsons featured it prominently in an episode. Tom Waits wrote an album of songs inspired by it. Gottfried Helnwein replaced the sitters with Marilyn Monroe, Humphrey Bogart, James Dean and Elvis in Boulevard of Broken Dreams. Joyce Carol Oates penned a novel giving an interior life to the pictured characters.

Painter: Lee Krasner

Year: 1949

Krasner's work from 1949 deploys hieroglyphic like signs against a grid. These signs, or glyphs have no specific meaning allowing the viewer to revel in the secret world of signs. Her “all-over” technique influenced Pollock's work; and, let's face it, without her there would be no “him.”

Painter: Jackson Pollock

Year: 1950

Pollock famously worked with the canvas on the floor, using any means necessary to muscle paint around. Pollock admitted that these seemingly abstract “drip” paintings were sometimes representational, adding that “when you're working out of your unconscious, figures are bound to emerge.” Let me translate that for you: look at something long enough and see…

Painter: Eric Fischl

Year: 1979

Should we be allowed to gaze at the sleepwalking boy standing in a kiddie pool? Is he urinating? masturbating? Fischl has the uncanny ability to make the viewer into voyeur, however, the more we look at this painting, the less we understand.

Painter: Robert Motherwell, LXX

Year: c. 1961

Motherwell was only a teenager during the Spanish Civil War, but it affected him deeply. He made more than 200 paintings on this theme. I could make an argument here for symbols, forms and abstraction, but let's just call a penis, a penis.

Painter: Alma W. Thomas

Year: c. 1973

Thomas used short strokes of blue color reminiscent of mosaic tesserae to create this work of accessible and affective abstraction. Lean back in your desk chair right now and imagine this painting in place of your ceiling. Dreamy, right? So magical that the Obamas chose it for their private quarters at the White House.

Painter: Patrick Nagel

Year: c. 1980s

Think of the woman from Duran Duran's Rio album cover. Or maybe you remember his illustrations from your dad's Playboy magazines? The Nagel “woman” is highly stylized with bright white skin and black hair. She is rendered in two-dimensional form marked with bright colors.

Painter: Keith Haring and Andy Warhol

Year: 1985

Haring and Warhol famously collaborated on this project in which Haring's delicate graffiti handwork compliments Warhol's silkscreened newspaper “headlines.” The duo gave this pop + graffiti mash up to Madonna and Sean Penn for their 1985 Malibu wedding.

Painter: Kara Walker

Year: 1996

Kara Walker is best known for mounting large black silhouettes, and organizing them into antebellum scenes on white gallery walls. Themes taken up in these passages include race, sexuality, region and history. The phantasmagorical Allegory reveals Walker's painterly roots.

Painter: Vincent Desiderio

Year: 2002

This triptych pays homage to the three-panel altarpiece form so popular during the Renaissance. Three seemingly unrelated pieces are linked together: the all-seeing powerful eye of the satellite rhymes with the cleft of the woman's buttocks and the window of the tower. Pantocrator, the Byzantine term for ruler of all, powerfully articulates the increasingly menacing role of science and technology in our everyday lives.

Painter: Thomas Cole

Year: 1836

Movement is the key to understanding this painting. As seen from Mount Holyoke, the Oxbow was formed when the Connecticut River pushed past its banks to create a curved shape. If the painting is read from right to left, its mood is ominous; there is nothing but storms ahead. Read from right to left, optimism reigns; the storm has passed and left sunshine in its wake.

Painter: Marsden Hartley

Year: 1914

Hartley's portrait of a fallen friend, Karl von Freyburg, is awash in symbols and riotous color. The palette is Fauvist, while the splintered view is standard Cubism. The numeral four may be reference to his friend's regiment, while twenty-four marks the age at which his dear friend was slain. Many scholars have ascribed the portrait's deeply emotional nature to the fact that Freyburg and Hartley may have been lovers.

Painter: Peter Saul

Year: 2006

Saul's acid-hued painting features a grinning President George W. Bush, who embraces a misshapen, bullet-ridden Iraqi soldier with one arm, while probing the distorted soldier's mouth with another. Bush's gesture could be influenced by a number of art historical sources. One wonders which gesture Saul references: The trader in Gerome's The Slave Market exploring the mouth of a potential human purchase? Or is Caravaggio's Doubting Thomas poking his hands into Christ's wounds. Ultimately, only Saul knows…

Painter: Cheyenne Tribe

Year: ca. 1870s

Until the second half of the nineteenth century Plains Indians often recorded their oral traditions in paintings on rocks, cave walls, and tipis. Once explorers forged west, ledgers were introduced and a new form, the ledger painting, was born. Artists used watercolor and pencils to capture important events. In this painting, a warrior takes part in a raid.

Painter: Norman Rockwell

Year: 1943

Rockwell painted a quartet of canvases for the Four Freedoms Series inspired by an FDR speech; the Four Freedoms included freedom of expression, freedom of worship, freedom from fear, and freedom from want. Freedom from Want was reproduced in an edition of the Saturday Evening Post, a place where many Americans saw Rockwell's iconic domestic images. This painting is emblematic of Rockwell's disturbing nostalgia: all is mostly well, except for the strange-looking boy in the back rear of the composition.