Painting is an ancient art that, despite the advent of photography, film, and digital technologies, has remained a popular means of expression. Only a small percentage of the paintings that have been limned over millennia are regarded “timeless classics” that have become well-known to the general public—and not surprisingly, painted by some of the most famous artists of all time.

The question of what mix of skill, intellect, and situation results in the creation of a masterpiece has yet to be solved. The simplest response is that you’ll recognise one when you see one, whether it’s in one of New York City’s many museums (The Metropolitan Museum, the Guggenheim, MoMA, and others) or elsewhere in the world.

Of course, we have our own opinions on what constitutes a great painting, and we’ve included them in our list of the best works of art ever created.

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

Da Vinci’s captivating picture, painted between 1503 and 1517, has been haunted by two questions from the day it was created: What is the subject’s name, and why is she grinning? Over the years, a variety of explanations have been proposed to explain the former: 

That she is the Florentine merchant Francesco di Bartolomeo del Giocondo’s wife (hence the work’s alternate title, La Gioconda); that she is Leonardo’s mother, Caterina, conjured from Leonardo’s early memories of her; and, finally, that it is a self-portrait in drag. 

For generations, the enigmatic character of that famed smile has driven people insane. Whatever the cause, Mona Lisa’s serene expression matches the idealized countryside behind her, which fades into the distance thanks to Leonardo’s airy perspective.

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

The 1665 study of a young woman by Johannes Vermeer is astonishingly genuine and strikingly modern, almost like a snapshot. This brings up the question of whether Vermeer used a pre-photographic instrument known as a camera obscura to create the image. 

Leaving that aside, the sitter’s identity is unknown, however it has been suggested that she was Vermeer’s maid. He depicts her staring over her shoulder, her eyes locked on the viewer, as if striving to create a personal connection across ages. Girl isn’t technically a portrait, but it is an example of the Dutch tronie—a headshot that is more of a still life of facial features than an attempt to recreate a resemblance.

3. Vincent van Gogh, The Starry Night, 1889

The Starry Night, Vincent Van Gogh’s most famous painting, was made at the asylum in Saint-Rémy, where he had committed himself in 1889. Indeed, the night sky comes alive with swirls and spheres of frantically applied brush strokes rising from the yin and yang of his own demons and wonder of nature in The Starry Night, which seems to mirror his stormy state of mind at the moment.

4. Gustav Klimt, 1907–1908, The Kiss

The Kiss, Gustav Klimt’s fin-de-siècle picture of intimacy, is a mix of Symbolism and Vienna Jugendstil, the Austrian form of Art Nouveau, and is lavishly gilded and lavishly patterned. Klimt portrays his protagonists as mythological figures who have been modernized by opulent surfaces adorned with current graphic patterns. The painting is a highlight of the artist’s Golden Period, which from 1899 to 1910 and saw him frequently employ gold leaf—a technique inspired by a 1903 visit to Ravenna, Italy’s Basilica di San Vitale, where he witnessed the church’s iconic Byzantine mosaics.

5. The Birth of Venus, 1484–1486 by Sandro Botticelli

Botticelli’s The Birth of Venus, painted for Lorenzo de Medici, was the first full-length, non-religious nude since antiquity. The Goddess of Love is said to be based on a woman named Simonetta Cattaneo Vespucci, whose favors were purportedly shared by Lorenzo and his younger brother, Giuliano. The wind gods Zephyrus and Aura are shown blowing Venus ashore on a large clamshell, as the personification of spring waits on land with a cloak. Savonarola, the Dominican friar who led a fundamentalist onslaught on the Florentines’ secular preferences, was understandably enraged by Venus. The iconic “Bonfire of the Vanities” in 1497, in which “profane” objects—cosmetics, artworks, and books—were destroyed, was part of his crusade.

Wrap up:

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