ARTnews wondered which paintings would be chosen by artists, museum directors, curators, and art historians today as the “greatest.”

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“The greatest picture in the world…you smile,” wrote Aldous Huxley in 1925. Although the claim sounded ludicrous to him, he went on to make a passionate and cogent argument for his choice: Piero della Francesca’s Resurrection. ARTnews wondered which paintings would be chosen by artists, museum directors, curators, and art historians today as the “greatest.” To find out, we queried a number of them. Many, understandably, declined to participate. A few struggled with their choices, and several circumvented the question—as in the case of Lawrence Rinder, the director of University of California Berkeley Art Museum and Pacific Film Archive, who chose a painting in his museum’s collection, which he sees often and knows well.

Some of the works selected tell stories of first love, beauty, and awakening; others hint at mysteries, angst, and defiance. In taking the question seriously, and not so seriously, the respondents collectively affirm that an artwork’s price and popularity are only surface criteria. What is valuable are the more subtle and powerful insights that reside in some of humanity’s most resonant examples of painterly expression.

The Altamira Cave Paintings in Cantabria, Spain.

RAMEESSOS/WIKIMEDIA

– Altamira Cave Paintings, Cantabria, Spain. “As I understand it, these paintings were made 15,000 years ago by people lying on their backs painting the ceiling by torchlight a mile into a dark cave. The images were a distillation of actual sights seen. The Altamira Cave paintings remain ritual, spiritual, essential, and magical.” —Richard Serra, artist

Saturn Devouring His Son(1820–23) by Goya.

COURTESY THE PRADO

– Francisco de Goya, Saturn Devouring His Son (1820–23), Prado, Madrid. “It is an unbelievably powerful painting. It remains timeless, universal, and forever relevant. It reflects our own anxieties as human beings mixed with social anxiety and political anxiety. The artist’s personal anxiety, his anguish, is embedded in the work. The first time I saw it, I was horrified and couldn’t breathe.” —Shirin Neshat, artist

The Isenheim Altarpiece (1512–16) by Matthias Grünewald.

COURTESY UNTERLINDEN MUSEUM

– The Isenheim Altarpiece by Matthias Grünewald (1512–16), Unterlinden Museum, Colmar, France. “Even in the 20th century, its influence has been profound for artists, including Max Beckmann, Pablo Picasso, Barnett Newman, and Jasper Johns. But most important, while its meaning, interpretation, and reasons for influence have shifted over the centuries, for me it is a painting that may be seen as contemporary, that is relevant for our own time, which is essential for any painting to be considered as the greatest painting.” —Gary Garrels, senior curator of painting and sculpture, San Francisco Museum of Modern Art

Malevich, Black Suprematic Square, 1915.

COURTESY STATE TRETYAKOV MUSEUM

– Kazimir Malevich, Black Suprematic Square (1915), State Tretyakov Gallery, Moscow. “Malevich described it as the ‘zero of form.’ In her recent book, Aleksandra Shatskikh pronounces it ‘the visual manifestation of a new period in world artistic culture at its inception.’ Boris Groys has written that the work is ‘the most radical gesture towards the acceptance of the total destruction of tradition.’ There are no Mona Lisa–style crowds signaling that you have arrived at a masterpiece, but Black Suprematic Square is surely a painting that possesses ineffable immensity.” —Kate Fowle, chief curator, Garage Center for Contemporary Culture, Moscow

Young Lady in 1866 (1866) by Manet.

COURTESY METROPOLITAN MUSEUM OF ART

–Édouard Manet, Young Lady in 1866 (1866), Metropolitan Museum of Art, New York. “Young Lady in 1866 shows Manet to be a consummate painter who rivals Velázquez. I always smile when I see it. It never disappoints in its urbanity, wit, and cleverness. It imparts a male presence without a male. It’s as if there should be a top hat tossed in the corner. It exudes sexuality in the most discreet and sophisticated way imaginable.” —Gary Tinterow, director, Museum of Fine Arts, Houston

Another Reinhardt, from the collection of the Museum of Modern Art, Abstract Painting, 1963.

COLLECTION OF MOMA

– Ad Reinhardt, Abstract Painting No. 3 (1960–63), Berkeley Art Museum and Pacific Film Archive, California. “What is remarkable about this painting—as well as many of Reinhardt’s later works—is that it can make sense of one’s own deepening consciousness of its qualities (color, shape, scale). It is a work of art that awakens one’s mind to itself.” —Lawrence Rinder, director, Berkeley Art Museum and Pacific Film Archive

Detail of Nine Dragons.

COURTESY MFA BOSTON

– Chen Rong, Nine Dragons (dated 1244), Museum of Fine Arts, Boston. “Chen Rong’s Nine Dragons embodies the humanism of China’s classical tradition, its polity, and its moral philosophy: dragons symbolize imperial power and order in national life, and they embody qi, the cosmic energy that animates the natural universe in Taoism. By tossing the dragons’ ferocious antics in the midst of nature’s impassive flux, the painting expresses on both pictorial and conceptual levels the yin-yang interplay of form and formlessness, substance and dynamism, flesh and eternity.” —Alexandra Munroe, senior curator of Asian Art, Guggenheim Museum

Dort, or Dordrecht: The Dort Packet-Boat from Rotterdam Becalmed (1818) Turner.

COURTESY YALE CENTER FOR BRITISH ART

– J. M. W. Turner, Dort or Dordrecht: The Dort Packet-Boat From Rotterdam Becalmed (1818), Yale Center for British Art, New Haven. “Only when seeing the painting over time and under different illumination can one appreciate its extraordinary responsiveness to light, adapting in a way that makes the painting almost seem to breathe.” —Amy Meyers, director, Yale Center for British Art

Velázquez, Las Meninas, ca. 1656.

COURTESY THE PRADO

– Diego Velázquez, Las Meninas (ca. 1656), Prado, Madrid. “The peculiar sense of never being able to finish looking at this painting has always stayed with me. Every time I approach the painting, it’s as if I’m stepping outside of my reality and being pulled toward the pictorial space that Velázquez created.” —Dan Cameron, chief curator, Orange County Museum of Art

The Mona Lisa (1503–17) by Leonardo.

COURTESY THE LOUVRE

– Leonardo da Vinci, Mona Lisa (1503–17), Louvre, Paris. “If we define greatness as having exercised the greatest hold over cultural imaginations across the world, there is only one answer: the Mona Lisa. I’m sorry to trigger a collective groan, but that’s how it is. Leonardo poured all his skill and all his philosophy of art and nature into it over a number of years. That’s a lot to pour in.” —Martin Kemp, emeritus professor of the history of art, University of Oxford

There are some questions in the art world that are not well received. Most of these have to do with money and rank. Asking how much an artwork costs or how important it is can seem a little crass and demeaning to the intensely personal experience of viewing high art.

James Oles, professor of art history at Wellesley College and a specialist in Latin American art, focusing on modern Mexican art and architecture, compared individual involvement with an artwork to a kind of knowledge that is as elusive as falling in love, and the idea of justifying or ranking such an effect as pointless.

“One might say that works of art that generate multiple and complicated interpretations from a variety of perspectives (often conflicting), and manage to do so over a long period of time to a wide variety of audiences . . . are perhaps somehow, well, more interesting than others, though with the caveat that sometimes minor or idiosyncratic works of art can be even more ‘important’ at a given moment,” Oles said. “But an engagement—emotional or intellectual—that would lead anyone to even consider saying or thinking any particular work of art is the ‘greatest’ is like their experience of falling in love: nice for them, but in actuality blinding, easily idealized, terribly individualized, rarely a model for the behavior of others, and ultimately rather meaningless in the grand scheme of things.”

And most emphatic was art historian Svetlana Alpers’s response: “I am sorry, but naming the greatest painting in the world is not a game I want to play. It has never occurred to me to be a question, and I am not going to consider it now.”

Even Gary Tinterow, director of the Museum of Fine Arts, Houston, who preferred to name his favorite, rather than the “greatest,” painting (Édouard Manet’s Young Lady in 1866) described his state in the face of the query as “kicking and screaming. I don’t believe it is a relevant question.” Lawrence Rinder likewise expressed reservations in his selection of Ad Reinhardt’s Abstract Painting No. 3, a favorite painting in the Berkeley Art Museum’s collection. “It is an interesting thought exercise,” he said. “While I don’t believe that there is a ‘greatest painting,’ pondering this question has had the benefit of causing me to reflect on many paintings that I know and love.”

Nearly a century ago, Huxley anticipated a similar kind of reaction when he dedicated his 1925 essay, “The Best Picture,” to the splendor of Piero’s Resurrection (1467–68). “The expression is ludicrous, of course,” he wrote. “Nothing is more futile than the occupation of those connoisseurs who spend their time compiling first and second elevens of the world’s best painters, eights and fours of musicians, fifteens of poets, all-star troupes of architects and so on. Nothing is so futile because there are a great many kinds of merit and an infinite variety of human beings. Is Fra Angelico a better artist than Rubens? Such questions, you insist, are meaningless. It is all a matter of personal taste. And up to a point this is true. But there does exist, none-the-less, an absolute standard of artistic merit.”

Jackson Pollock once proclaimed José Clemente Orozco’s giant mural of Prometheus at Pomona College in California, completed in 1930, “the greatest painting done in modern times.” Barnett Newman considered Matthias Grünewald’s painting of the Crucifixion in the Isenheim Altarpiece at Colmar “maybe the greatest painting in Europe.” And, in Marcel Proust’s opinion, Vermeer’s View of Delft (1660–61) was the world’s most beautiful painting. As Newman observed to ARTnews editor Thomas Hess in 1966, “The problem of ambition moves in all kinds of areas, but in the studio you do the greatest painting that has ever been made—not the greatest painting that you can make—the greatest painting that has ever been made. And to that extent the dialogue moves in relation to Michelangelo or Cézanne or whoever it is.”

But contemplating what makes a work “the greatest” is “very large and complicated,” said painter James Rosenquist, citing such possible choices as the prehistoric cave paintings, Michelangelo’s Sistine Chapel, Braque and Picasso’s Cubism, the French Impressionists’ treatment of color, Kandinsky and Malevich’s non-objective painting, and modern Americans Hans Hofmann and Joan Mitchell, “who never let extraneous images accidentally into their paintings.”

“In history, there have been many incredible ‘best’ paintings. And one is very lucky to learn from them,” said Rosenquist. “I tell young art students that some of the most famous paintings in some of the most famous museums are done with minerals mixed in oil and smeared on cloth with a hair from the back of a pig’s ear—which are fine Chinese bristle brushes. And some of the greatest drawings are merely done with burned wood drawn on parchment or some kind of paper.”

Today, critical voices strain to compete with an international press that is more likely to look to price or popularity as a statement of a work’s importance. When Francis Bacon’s Three Studies of Lucian Freud(1969) sold for $142.4 million at Christie’s in November 2013 (overriding the previous record holder, Edvard Munch’s $120 million The Scream), New York Times critic Roberta Smith wrote, “More than ever, the glittery auction-house/blue-chip gallery sphere is spinning out of control far above the regular workaday sphere where artists, dealers and everyone else struggle to get by. It is a kind of fiction that has almost nothing to do with anything real—not new art, museums or historical importance.”

Smith added that the triptych “might also be termed a portrait of a middlebrow artist by another middlebrow artist.” When an American Idol–like BBC poll selected J. M. W. Turner’s The Fighting Temeraire (1839) as the greatest painting in Britain in 2005, the late critic Robert Hughes told a Scottish newspaper, “As for saying what is the greatest, the fastest, the thinnest, and all that stuff, is not what I am into. In my opinion there is nothing to which it could be relevant except a minor circulation-building exercise.”

According to Amy Meyers, director of the Yale Center for British Art, time and historical context aren’t always kind to the “greatest” label. In the later 18th century, Meyers says, Nicolas Poussin’sTestament of Eudamidas (1644–48), “was considered one of the greatest paintings in the world, its fame spread through the engravings of Jean Pesne and Marcenay de Ghuy. Then it was held up as an example of excellence for artists and imitated widely. Nowadays visitors to the National Gallery of Denmark can pass by this small painting without a second glance.

“In the same way,” Meyers continued, “Thomas Gainsborough was perhaps the best-known artist in the world in the early 20th century, when portraits like The Blue Boy reached the United States. A century on, if you stopped someone and asked them to list the names of great artists, Gainsborough’s name would scarcely ever be mentioned,” she pointed out. “Neither Poussin nor Gainsborough is a better or worse painter today than they were in 1760 or 1900, but our judgments and discriminations about the greatness of paintings and painters are mutable.”

While for artist Shirin Neshat, greatness in art means “transcending all differences, despite where an artist is from,” for some people, the definition of “greatness” itself is problematic. “If it means painting as painting, then Velázquez’s Las Meninas takes some beating,” according to Martin Kemp, emeritus professor of the history of art at the University of Oxford. “The Rembrandt self-portrait at Kenwood in London is in the same league. If we mean the most epoch-changing, we would look to Masaccio’sTrinity or Picasso’s Les Demoiselles d’Avignon. If we mean my all-time favorite, it would probably be Bellini’s Saint Francis in the Frick.”

Some paintings, such as Picasso’s Les Demoiselles d’Avignon (1907), have had tremendous impact in art history and are as famous for not being seen in the years following their creation as for their place in textbooks today. “From the mid-1930s to the late 1980s, Malevich’s Black Square, along with works by many other artists, went unseen and unaccounted for in the Soviet Union, and until the late ’50s were virtually unknown elsewhere,” said Kate Fowle, chief curator of the Garage Center for Contemporary Culture in Moscow.

“What we (I) take for granted as the legacy contemporary Russian artists inherited was, for years, a void in itself,” she said. “The question is, how many potentially ‘greatest’ works have never been exposed to enough people to even stand the chance of being recognized as such?”

A certain criterion for the greatest painting in the world is the test of time, said Alexandra Munroe, senior curator of Asian art at the Guggenheim Museum. “Has the painting spoken across centuries, or if it’s modern, can you imagine that it could? Does it express the highest order of human thought its civilization developed, or perhaps, like Picasso’s Guernica, express its basest? Have the arbiters of later cultures regarded the work as a touchstone of universal humanity, assuming relativism hasn’t made such a claim irrelevant? And has the artistic virtuosity of its expressive powers been surpassed? Tens if not hundreds of pictures by artists around the world throughout history could qualify. What’s arbitrary, personal, and wonderful is which one you might select at any given moment in your life.”

Ultimately, the passage of time reveals the vulnerability of “greatness” itself. “Future generations undoubtedly will look back at our lists and disagree, just as we look back at earlier assessments of the greatness of works of art and are left surprised or bemused by how our forbears judged works of art and came to their assessments of artistic value,” said Meyers. “But that in itself is an illuminating insight into the taste and reasoning of an earlier generation, and a reminder to us that our value judgments are fallible and disclose much more about us than we might realize.”