The most famous paintings of all time

When ranking the most famous paintings of all time, we have to realize that the act of painting is an ancient medium, dating as far back as 40,000 years ago, when early humans applied ochre and charcoal to cave walls to create images of animals or stencils of their own handprints. It was, in other words, present at the birth of symbolic thought, predating the written word by 35,000 years or so.

Even with the onset of the modern era, and the introduction of photography, film and digital technology, painting has remained a persistent mode of expression, in spite of cyclic pronouncements of its death.

It's impossible to say just many paintings have been limned over dozens of millennia, only that a relatively small percentage of them could be construed as timeless classics that have become familiar to the public—and not coincidentally produced by some of the most famous artists of all time. That may be stating the obvious, but it leaves open the question of what mix of talent, genius and circumstance leads to the creation of a masterpiece. Perhaps the simplest answer is that you know one when you see one, whether it's at one of NYC's many museums (The Metropolitan Museum, the Guggenheim, MoMA and elsewhere) or at institutions in other parts of the world. We, of course, have our opinion of what makes the grade and we present them here in our list of the best paintings of all time.

1. Leonardo Da Vinci, Mona Lisa, 1503–19

Painted between 1503 and 1517, Da Vinci’s alluring portrait has been dogged by two questions since the day it was made: Who’s the subject and why is she smiling? A number of theories for the former have been proffered over the years: That she’s the wife of the Florentine merchant Francesco di Bartolomeo del Giocondo (ergo, the work’s alternative title, La Gioconda); that she's Leonardo’s mother, Caterina, conjured from Leonardo's boyhood memories of her; and finally, that it's a self-portrait in drag. As for that famous smile, its enigmatic quality has driven people crazy for centuries. Whatever the reason, Mona Lisa’s look of preternatural calm comports with the idealized landscape behind her, which dissolves into the distance through Leonardo’s use of atmospheric perspective.

2. Johannes Vermeer, Girl with a Pearl Earring, 1665

Johannes Vermeer’s 1665 study of a young woman is startlingly real and startlingly modern, almost as if it were a photograph. This gets into the debate over whether or not Vermeer employed a pre-photographic device called a camera obscura to create the image. Leaving that aside, the sitter is unknown, though it’s been speculated that she might have been Vermeer's maid. He portrays her looking over her shoulder, locking her eyes with the viewer as if attempting to establish an intimate connection across the centuries. Technically speaking, Girl isn’t a portrait, but rather an example of the Dutch genre called a tronie—a headshot meant more as still life of facial features than as an attempt to capture a likeness.

3. Sandro Botticelli, , 1484–1486

Botticelli’s The Birth of Venus was the first full-length, non-religious nude since antiquity, and was made for Lorenzo de Medici. It’s claimed that the figure of the Goddess of Love is modeled after one Simonetta Cattaneo Vespucci, whose favors were allegedly shared by Lorenzo and his younger brother, Giuliano. Venus is seen being blown ashore on a giant clamshell by the wind gods Zephyrus and Aura as the personification of spring awaits on land with a cloak. Unsurprisingly, Venus attracted the ire of Savonarola, the Dominican monk who led a fundamentalist crackdown on the secular tastes of the Florentines. His campaign included the infamous “Bonfire of the Vanities” of 1497, in which “profane” objects—cosmetics, artworks, books—were burned on a pyre. The Birth of Venus was itself scheduled for incineration, but somehow escaped destruction. Botticelli, though, was so freaked out by the incident that he gave up painting for a while.

4. Vincent van Gogh, The Starry Night, 1889

Vincent Van Gogh’s most popular painting, The Starry Night was created by Van Gogh at the asylum in Saint-Rémy, where he’d committed himself in 1889. Indeed, The Starry Night seems to reflect his turbulent state of mind at the time, as the night sky comes alive with swirls and orbs of frenetically applied brush marks springing from the yin and yang of his personal demons and awe of nature.

5. James Abbott McNeill Whistler, Arrangement in Grey and Black No. 1, 1871

Whistler’s Mother, or Arrangement in Grey and Black No. 1, as it’s actually titled, speaks to the artist’s ambition to pursue art for art’s sake. James Abbott McNeill Whistler painted the work in his London studio in 1871, and in it, the formality of portraiture becomes an essay in form. Whistler’s mother Anna is pictured as one of several elements locked into an arrangement of right angles. Her severe expression fits in with the rigidity of the composition, and it’s somewhat ironic to note that despite Whistler’s formalist intentions, the painting became a symbol of motherhood.