1. Les Demoiselles d'Avignon (1907), Pablo Picasso
The ur-canvas of 20th-century art, Les Demoiselles d'Avignon ushered in the modern era by decisively breaking with the representational tradition of Western painting, incorporating allusions to the African masks that Picasso had seen in Paris's ethnographic museum at the Palais du Trocadro. It's compositional DNA also includes El Greco's The Vision of Saint John (1608--14), now hanging in the Metropolitan Museum of Art. The women being intruded upon by the small still-life at the bottom of frame are actually prostitutes in a brothel. An early study for the painting featured a medical student entering from the left to make his selection for the night, but Picasso wisely decided to leave him out in the final composition, leaving only Avignon in the title as a clue to his subject's origin: It's the name of a street in the artist's native Barcelona, famous for its cathouses.
2. Gold Marilyn Monroe (1962), Andy Warhol
No Warhol demonstrates the artist's worship of glamour better than this painting, created the year Monroe died in an apparent suicide. It is the altarpiece in Andy's Pop Art church of celebrity. But by the same token, the work also speaks to Warhol's background as an observant Catholic; it wouldn't look all that out of place at St. Peter's Basilica in Rome or at St. Patrick's Cathedral on Fifth Avenue, where Warhol regularly attended mass (sans wig). The image is based on a publicity still for the film Niagara, in which Monroe played opposite Joseph Cotton as an unhappily married woman, plotting the murder of her husband.
3. Self-Portrait with Cropped Hair (1940), Frida Kahlo
This gender-bending self-portrait by the celebrated Mexican artist and feminist icon was occasioned by her divorce from Diego Rivera---the muralist notable not only for his own artistic genius, but for his philandering ways. Kahlo had apparently enough of the latter, but as the painting indicates, she couldn't quite quit Rivera. She pictures herself in a chair, hair shorn, with her signature peasant blouse and skirt replaced by Rivera's clothes---effectively transforming herself into her ex-husband's likeness. Her locks, now scattered across the floor, seem to writhe menacingly around her, and she captioned the composition with the words from a popular Mexican love song: "Look, if I loved you it was because of your hair. Now that you are without hair, I don't love you anymore." Unsurprisingly, Kahlo remarried Rivera the following year, so this weirdly compelling painting could also be described as a monument to codependency.
4. Flag (1954--55), Jasper Johns
Johns has said that the idea of painting the flag came to him in a dream, and while the image of the Stars and Stripes appears elsewhere in American art, no one transcribed the subject as literally as the artist did here: The canvas is the same shape and size as a typical flag, all but eradicating the distinction between the object and its representation. Of course, that isn't entirely the case. Created with encaustic---pigment mixed into melted wax---Flag, with its drips and smears seemingly frozen into place, is indubitably painted, and one can easily see a collage of newspaper strips running beneath the colors. Still, it serves as a banner for an artist who fired some of the first shots against Abstract Expressionism, the dominant style at the time, helping to usher in a new era of American art defined by Pop Art and Minimalism.
5. The Piano Lesson (1916), Henri Matisse
One of the artist's most personal pieces, The Piano Lesson shows Matisse's son Pierre at the keyboard. It's a composition about space, but also about time, as it echoes again and again the pyramidal shape of the metronome on the piano---in the band of green slicing across a casement to the left, and in the shadow falling across Pierre's face. He is set between two of his father's works depicting females, the matronly Woman on a High Stool and a small sculpture of a sensuous, reclining nude. More than a simple description of a family life, The Piano Lesson serves as a meditation on manhood, and one boy's impending introduction to it.
6. Woman I (1950--52), Willem de Kooning
In the signature painting of De Kooning's career, the artist jokingly inserts an interplay between enormous eyes and breasts (strapped down here as if they might burst from the picture plane and smother the viewer), taunting us with the question, which would you look at first? The flurry of violent marks defining the figure could be easily read as misogynistic, but complaining about misogyny in New York's postwar art world is a bit like complaining that Rembrandt didn't have electric lights. With her verticality and frontal positioning, Woman I seems enthroned: the regent of De Kooning's imagination.
7. Drowning Girl (1963), Roy Lichtenstein
Lichtenstein's Pop icon is at once a coolly ironic deconstruction of pulp melodrama and a formally dynamic---even moving---composition, thanks largely to the interplay of the subject's hair (swept into a perfect Mad Men--era coif) and the waves (which seem to have wandered in from a Hokusai print) threatening her. The image, a crop from a panel in an early-'60s comic book titled Run for Love!, shows that Lichtenstein's in full command of his style, employing not only by his well-known Ben-Day dots, but also bold black lines corralling areas of deep blue. It's a complete stunner.
8. Broadway Boogie Woogie (1942--43), Piet Mondrian
Mondrian came to New York in 1940, fleeing the Nazi invasion of his native Holland. He died here four years later, and though he probably didn't know it at the time, his brief sojourn would have a lasting, if delayed, impact on American art. Though AbEx put the U.S. on the map, Minimalism was to become our most enduring stylistic export, and its rigorous, reductive geometry owed a lot to Mondrian's de Stijl aesthetic. Broadway Boogie Woogie, his second to last painting, is a love letter to his adopted home, inspired by jazz and the energy of the Gotham's streets---a strangely prescient, if abstract, portrait of the city as the center of a nascent superpower.
9. The Persistence of Memory (1931), Salvador Dal
Dal described his meticulously rendered works as "hand-painted dream photographs," and certainly, the melted watches that make their appearance in this Surrealist masterpiece have become familiar symbols of that moment when reverie seems to uncannily invade the everyday. The coast of the artist's native Catalonia serves as the backdrop for this landscape of time, in which infinity and decay are held in equipoise. As for the odd rubbery creature in the center of the composition, it is the artist himself, or rather his profile, stretched and flattened like Silly Putty.
10. The Bather (c. 1885), Paul Czanne
Czanne was that most contradictory type of modern artist: a radical conservative who pushed the envelope of late-19th-century painting, while also trying to maintain ties to art-historical tradition. The Bather is exemplary in this regard, a balancing act between timeless subject matter and avant-garde technique. With his flaccid musculature and awkward posture, the eponymous figure is both monumental and yet decidedly unheroic, and Czanne describes him in a flurry of brushstrokes that threaten to meld into the background. At once contemporary and classical, The Bather represents transcendent form fashioned from the clay of ordinary experience.
11. Masks Confronting Death (1888), James Ensor
Ensor was born and spent the bulk of his career in the Belgian seaside resort of Ostend, which, like New Orleans, is famous for an annual masquerade. Ensor's family owned a small emporium that catered to tourists, selling oddities, seashells and carnival masks of the sort that populate compositions like this one. Indeed, though it appears that Ensor is juxtaposing the natural with the supernatural in this painting, he isn't describing some dream or premonition. The elements here are clearly props---masks and skulls plopped onto heaps of clothing. Ensor was obsessed with mortality, especially his own, but he wasn't lugubrious about it; he treated death as a cosmic joke. Considering that he lived until he was 89, he had a long time to laugh at it.
12. M'Amenez-y (1919--20), Francis Picabia
Picabia was modernism's original bad boy, a writer as well as a painter who, along with Man Ray and Marcel Duchamp, helped to spread the Dada contagion from Europe to New York City. A self-described "pickpocket" and "imbecile," Picabia was a consummate antiartist whose love of language, especially puns, and disregard for artistic convention are on full display in this painting: It includes snarky observations about artistic craft (the phrase along the top edge translates as "portrait with castor oil," a comparison of the foul-tasting laxative with the linseed oil used by painters), plus the machine imagery that characterized the artist's Dadaist phase.
13. The Sleeping Gypsy (1897), Henri Rousseau
Rousseau's career represents the first instance, perhaps, of a self-taught outsider artist who won the admiration of insider peers, though the road to recognition wasn't easy. The story goes that Picasso first stumbled upon the work of this toll-collector-turned-painter while it was being sold on the sidewalk as used canvas to be painted over. Since then, Rousseau's mix of dreamy naive figuration and exotic landscapes (all imagined; he never left France) has become indelible---never more so than in this painting, in which the juxtaposition of beauty and beast has an unearthly quality.
14. Three Women (1921--22), Fernand Lger
Sleek tubular forms are the hallmarks of Lger's style and certainly dominate this chic if slightly odd composition, depicting nude female models enjoying a kaffeeklatsch. In reality, the piece is harem scene out of Ingres, transposed to an upscale Parisian apartment, but what is especially notable about it---and most of Lger's work---is its serene, streamlined sensibility, evoking an unshakable faith in modernity's promise of the good life. That optimism, along with an almost comic-book-like propensity for bright colors and bold black outlines, defined Lger not only as modernist pioneer, but a precursor of Pop Art.
Ren Magritte, The Palace of Curtains, III (1928-29)
15. The Palace of Curtains III (1928--29), Ren Magritte
Magritte created this work around the same time as his much more familiar icon of a pipe that isn't, but it deals with the same theme: the slippery nature of represention, whether verbal or visual. Two framed objects---both vaguely coffin-shaped---lean side by side against a wainscotted wall, perhaps in a library or drawing room, though who really knows? One bears the French word for "sky," the other depicts a patch of blue scudded with clouds. Neither, however, conforms to the truth, Magritte seems to say, because language and painting are constructs of culture and nothing more. A true meta-mind-fuck, the piece expresses a deeply radically notion in a deceptively traditionalist fashion.
16. Embryo II (1967), Lynda Benglis
Benglis rocked the art world in 1974 with her ad for Artforum, in which she posed nude with a double-ended dildo between her legs, so the phallic shape of this beeswax on wood relief painted seven years earlier can be seen as a forerunner of that notorious piece. Its elongated form was inspired by the vertical stripes or "zips" in the paintings of Barnett Newman, whom Benglis met shortly after arriving in New York.
Robert Rauschenberg, Rebus (1955)
17. Rebus (1955), Robert Rauschenberg
This seminal painting by Rauschenberg is considered part of his series of "combines"---aggregations of three-dimensional objects with two-dimensional painting---though the piece itself is flatter than the typical combine from this period. Rebus is all about gritty urban tude: It's made up of hunks of fabric, newspaper comics and campaign flyers that Rauschenberg found in the streets surrounding his studio in lower Manhattan. He considered the work a capsule of a particular time and place.
18. Suprematist Composition: White on White (1918), Kazimir Malevich
Though it was painted nearly a century ago, this painting's radical nature continues to astonish. Malevich's aim wasn't pure reductivism, though. Inspired by Russia's icon tradition, the early Soviet avant-gardist believed that the Russian Revolution had ushered in a new age in which materialism would give way to spirituality. He called his philosophy Suprematism, and White on White serves as the supreme manifestation of the artist reaching for transcendence.
19. Vir Heroicus Sublimis (1950--51), Barnett Newman
Measuring 18 feet long and eight feet high, this canvas was meant to overwhelm the viewer's senses, and indeed, it does just that, especially if you view the painting as the artist intended: up close with your nose practically in it. Unlike other AbEx classics, Vir Heroicus Sublimis (the title is Latin for "man, heroic and sublime") isn't about the artist's emotions captured in a gesture---it's painted uniformly---but rather about the viewer's emotional response while confronting it.
20. Untitled (1961), Lee Bontecou
In the macho scene of postwar American art, Bontecou was a rare female presence, but when it came to making tough work, she could keep up with the boys and then some. This piece is made with industrial canvas salvaged from a conveyor belt that had been tossed out on the street by a laundry located below the artist's East Village apartment. The glowering form---suggesting a wormhole into some dimension of Cold War terror, or an eyepiece from a gas mask---was achieved by stretching fabric across a steel frame.