Painting is an ancient medium that has persisted as a form of expression despite the development of photography, film, and digital technologies. Only a small portion of the numerous paintings that have been preserved over many centuries and millennia can be considered “timeless classics” that are well-known artwork to the general public—and which, coincidentally, were created by some of the most well-known artists of all time.
It begs the issue of what confluence of ability, brilliance, and circumstance results in the production of a masterpiece. The easiest response may be that you can recognize one when you see one, whether it’s at one of the many museums in New York City (including The Metropolitan Museum, the Guggenheim, MoMA, and others) or at establishments abroad. Of course, we have our own opinions on what qualifies, and we’ve included those in this list of the greatest paintings ever created.
1. Leonardo Da Vinci, Mona Lisa, 1503–19
Da Vinci’s captivating portrait, which was painted between 1503 and 1517, has been the subject of two inquiries ever since it was created: Why is the subject smiling, and who is she? Over the years, a variety of ideas for the former have been put forth: That she is Caterina, Leonardo’s mother, as imagined from his childhood memories of her; that she is the spouse of Florentine merchant Francesco di Bartolomeo del Giocondo (thus the alternative title for the piece, La Gioconda); and finally, that it is a self-portrait dressed as another person. About that fabled smile, its enigmatic character has long baffled mankind. Whatever the cause, Leonardo’s use of atmospheric perspective allows the idealized landscape behind Mona Lisa to fade into the distance while maintaining her expression of unnatural peace.
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2. Johannes Vermeer, Girl with a Pearl Earring, 1665
The young woman in Johannes Vermeer’s 1665 study is astonishingly genuine and strikingly contemporary, almost like a snapshot. This raises the question of whether Vermeer used a camera obscura, a type of pre-photographic equipment, to generate the image. Other than that, no one is certain who the sitter was, however it has been suggested that she might have been Vermeer’s maid. She appears to be trying to establish an intimate connection across the ages as he paints her glancing over her shoulder and locking her eyes with the viewer. Strictly speaking, Girl isn’t a portrait at all, but an illustration of the Dutch headshot style known as a tronie, which is more of a still life of the contours of the face than an attempt to capture a resemblance.
3. Vincent van Gogh, The Starry Night, 1889
The Starry Night, Vincent Van Gogh’s most well-known picture, was produced by Van Gogh while he was a patient at the Saint-Rémy institution, where he had checked himself into in 1889. When the night sky comes alive with swirls and spheres of frenetically applied brush strokes arising from the yin and yang of his personal demons and awe of nature, The Starry Night does indeed seem to mirror his volatile state of mind at the time.
4. Gustav Klimt, The Kiss, 1907–1908
The Kiss, a depiction of intimacy by Gustav Klimt from the turn of the century that is lavishly gilded and lavishly patterned, combines Vienna Jugendstil, an Austrian take on Art Nouveau, with Symbolism. Klimt presents his subjects as mythological beings who have been modernized by lavish surfaces of contemporary graphic elements. The piece is a high point of the artist’s Golden Period, which spanned 1899 to 1910 and was characterized by the frequent use of gold leaf. This technique was motivated by a 1903 trip to Ravenna, Italy’s Basilica di San Vitale, where he witnessed the church’s renowned Byzantine mosaics.
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5. Sandro Botticelli, The Birth of Venus, 1484–1486
The Birth of Venus by Botticelli, which was created for Lorenzo de Medici, was the first full-length, non-religious nude since antiquity. The Goddess of Love is said to be based on Simonetta Cattaneo Vespucci, whose favors are said to have been shared by Lorenzo and his younger brother Giuliano. Zephyrus and Aura, the wind gods, are seen blowing Venus on a large clamshell to land where the personification of spring is waiting in a cloak. Naturally, Venus enraged Savonarola, the Dominican monk who oversaw a fundamentalist crackdown on the Florentines’ secular preferences. During his campaign, famed “Bonfire of the Vanities” in 1497 took place, in which “profane” items like books, paintings, and cosmetics were burned on a bonfire.
6. James Abbott McNeill Whistler, Arrangement in Grey and Black No. 1, 1871
Whistler’s Mother, also known as Arrangement in Grey and Black No. 1, expresses the artist’s desire to create art for the sake of creating art. In the piece, which James Abbott McNeill Whistler created in his London studio in 1871, the formality of portraiture takes on the form of an essay. Anna Whistler, Whistler’s mother, is depicted as one of several components arranged in a series of right angles. Despite Whistler’s formalist goals, the picture came to represent motherhood because of her stern countenance, which blends in with the composition’s rigidity.
7. Jan van Eyck, The Arnolfini Portrait, 1434
This composition, one of the most important works created during the Northern Renaissance, is said to be among the earliest oil paintings ever created. It is said to be a full-length double portrait of an Italian merchant and a woman who may or may not be his bride. The renowned art critic Erwin Panofsky said that the artwork is actually a marriage contract in 1934. It is safe to say that the painting is one of the first interiors to use orthogonal perspective to create a sense of space that is adjacent to the viewer’s own; it has the appearance of a picture you could enter.
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8. Hieronymus Bosch, The Garden of Earthly Delights, 1503–1515
Generally speaking, this weird triptych is seen as a distant precursor to surrealism. In actuality, it’s the expression of a late medieval artist who thought that Heaven, Hell, and the Devil were actual places. The left panel of the three images portrays Christ delivering Eve to Adam, while the right panel displays the wrath of Hell; it is less clear whether the middle panel shows Paradise. The damned are attacked by giant ears brandishing phallic knives in Bosch’s vivid depiction of Hell, while a bird-beaked bug king wearing a chamber pot as a crown sits on the throne and consumes the unfortunate before swiftly defecating them out again. Its riot of symbols has generally resisted interpretation, which would explain why it is so popular.
9. Georges Seurat, A Sunday Afternoon on the Island of La Grande Jatte, 1884–1886
The iconic image by Georges Seurat, which evokes the Paris of the Belle Epoque, really shows a working-class suburban scene outside the city’s core. Contrary to the bourgeois depictions of his Impressionist contemporaries, Seurat frequently made this milieu the subject of his paintings. Seurat chose the idea of eternal permanence found in Greek sculpture above the capture-the-moment style of Manet, Monet, and Degas. And that is just what you get in this procession of individuals that resembles a frieze; their immobility is consistent with Seurat’s intention to create a classical landscape in modern form.
10. Pablo Picasso, Les Demoiselles d’Avignon, 1907
Les Demoiselles d’Avignon, considered the founding work of 20th-century art, marked the beginning of the modern era by blatantly departing from the Western tradition of representational painting and incorporating references to the African masks that Picasso had seen in the Palais du Trocadro, Paris’s ethnographic museum. El Greco’s The Vision of Saint John (1608–14), which is currently on display at the Metropolitan Museum of Art, is also a part of its compositional DNA. In reality, the women being portrayed are prostitutes from a brothel in Barcelona, the artist’s hometown.
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