Sad paintings outlast happy ones. Ask people to name a painting that made them feel something and the answers are rarely picnics: they are a grieving man with his face in his hands, a girl in a fever bed, a jester who has just read the news, a woman alone at a table at night. The twenty paintings on this list are the ones that come up again and again when the question is asked, chosen because each has a documented reason for its sadness, a death, an illness, an exile, a war, a letter the artist wrote, rather than a vague air of gloom. Every entry tells you what the painting shows, what was happening when it was made, and where it hangs today. Seventeen are reproduced here; three, by Andrew Wyeth, Frida Kahlo and Pablo Picasso, are still under copyright and are described in words instead.
They run from the 1830s to the 1940s, which is not an accident. Earlier centuries painted grief constantly, but mostly as scripture: a Deposition, a Pietà, a Massacre of the Innocents. The paintings below are the ones where sorrow became the subject itself, ordinary and unredeemed. Many of the artists appear on our list of the most famous paintings of all time, and several painted themselves in the same spirit, which you can see in our list of famous self-portraits.
The 20 most famous sad paintings
1. Evening. Melancholy by Edvard Munch (1891)
What it shows: a man sitting on the shore at Åsgårdstrand, south of Oslo, head on hand, with the beach curving away behind him toward a jetty where two tiny figures stand by a boat. Why it is sad: the man is Munch’s friend Jappe Nilssen, in the middle of an unhappy love affair with a married woman, and Munch painted the subject several times through the 1890s; this early version, now in the Munch Museum in Oslo, is the one that fixed the pose. The long diagonal of the shoreline pulls the eye away from him toward the couple he is thinking about, which is the whole story in one line. Munch’s own writings from these years describe his art as coming from the “anxiety of life” that he said he carried from childhood, when his mother and his sister Sophie both died of tuberculosis. Where it is: the Munch Museum, Oslo; the 1892 version is in the National Museum, Oslo.
2. The Sick Child by Edvard Munch (1885 to 1886)
What it shows: a red-haired girl propped up on a pillow, her face turned toward a woman in black who bows her head and holds the girl’s hand, the paint scraped and scored until the surface looks worn through. Why it is sad: the girl is Munch’s sister Sophie, who died of tuberculosis in 1877 at fifteen, when he was thirteen; the model was a girl named Betzy Nielsen, and the grieving figure is usually identified as their aunt Karen. Munch said he reworked the picture more than twenty times, trying to get back to the first impression, and that it was his breakthrough. When it was shown in Oslo in 1886 critics called it unfinished and a sketch, and one described it as mashed fish. He returned to the subject for the rest of his life and painted six versions. Where it is: the National Museum, Oslo; later versions are at Tate in London and the Gothenburg Museum of Art.
3. Stańczyk by Jan Matejko (1862)
What it shows: a court jester in red slumped in a chair in a dark side room, hands clasped, cap and bells still on, while through the doorway behind him a royal ball goes on in candlelight. On the table beside him is a letter. Why it is sad: the letter announces the loss of Smolensk to Muscovy in 1514, and the jester, Stańczyk, who served three Polish kings, is the only person at court who understands what it means; the painting’s full title names the ball, given by Queen Bona, as the setting. Matejko painted it in 1862, a year before the failed January Uprising against Russian rule, and gave the jester his own face. In Poland it became the image of the thinking man who sees the catastrophe coming while everyone else dances. The painting disappeared during the Second World War and was returned from the Soviet Union in 1956. Where it is: the National Museum in Warsaw.
4. Inconsolable Grief by Ivan Kramskoi (1884)
What it shows: a woman in full black mourning standing in a drawing room beside a crate of wreaths and flowers, a handkerchief pressed to her lips, looking straight out of the picture. Why it is sad: Kramskoi, the leader of the Russian realist group known as the Wanderers, lost two of his young sons within a few years of each other in the late 1870s, and the painting grew out of that. He worked on it for about four years and made several versions, moving the figure from a seated pose to this standing one, and said that he painted it for himself rather than for sale. He offered it to the collector Pavel Tretyakov as a gift if Tretyakov would not buy a picture so bleak; Tretyakov bought it. The flowers are for a funeral that has already happened or is about to; nothing in the room tells you which. Where it is: the State Tretyakov Gallery, Moscow.
5. Sorrowing Old Man (At Eternity’s Gate) by Vincent van Gogh (1890)
What it shows: a bald old man in a blue smock sitting on a plain chair by a fire, bent double, both fists pressed into his eyes. Why it is sad: the pose comes from a drawing and a lithograph van Gogh made in The Hague in 1882 of a pensioner named Adrianus Zuyderland, which he titled “At Eternity’s Gate” in English. He painted this version in May 1890 in the asylum at Saint-Rémy, in the last weeks before he left for Auvers, where he died that July. In a letter about the 1882 drawing he wrote that he wanted to express the feeling of something noble in an old man who did not know he had it. The painting is the same subject made by someone who now knew the despair from the inside. Where it is: the Kröller-Müller Museum, Otterlo.
6. Sorrow by Vincent van Gogh (1882)
What it shows: a naked, pregnant woman sitting on a rock with her head buried in her arms, drawn in chalk, with the word “Sorrow” lettered along the bottom. It is a drawing rather than a painting, and it is on every list of this kind anyway. Why it is sad: the model is Clasina Maria Hoornik, called Sien, a pregnant seamstress and sometime prostitute whom van Gogh took in with her daughter in The Hague in 1882 and lived with for about a year and a half. He wrote to his brother Theo that he wanted to make figures that expressed sorrow, and he quoted the French historian Michelet along the lower edge: “How can there be on earth a woman alone, abandoned?” He called it the best figure he had drawn. The relationship ended in 1883 when he left for Drenthe. Where it is: the drawing is in the Walsall art gallery in England (the Garman Ryan Collection); van Gogh also made a lithograph of it.
7. Lachrymae by Frederic Leighton (about 1895)
What it shows: a woman in black classical dress leaning her head on her arm against a fluted column with an urn on top, a dark cypress behind her and a bright strip of sky beyond. The title is Latin for tears. Why it is sad: the column is a grave marker and the urn holds ashes; the cypress has been the tree of mourning since antiquity. Leighton, president of the Royal Academy, painted it in the last year of his life, when he was already ill with the heart condition that killed him in January 1896, and it was among the last pictures he exhibited. It is grief in the Victorian classical manner: no tears shown, the whole weight carried by the lean of the body and the black of the robe against the pale marble. Where it is: the Metropolitan Museum of Art, New York.
8. Sorrow (The Magdalen) by Paul Cézanne (about 1868 to 1869)
What it shows: a woman with loose hair and a heavy blue robe, kneeling and bent over with her face hidden in her hands, a skull at her side. Why it is sad: this is Cézanne before Cézanne, painted in his late twenties in thick, dark, violent strokes, the manner his friends called his “couillarde” period. The subject is Mary Magdalene as the penitent, a stock religious theme, but he strips it of saints and angels and leaves a woman alone with a skull, which is why the Musée d’Orsay catalogues it under both titles. It was originally part of a larger decoration painted directly for the family house, the Jas de Bouffan near Aix-en-Provence, and was cut from the wall and transferred to canvas. Where it is: the Musée d’Orsay, Paris.
9. Automat by Edward Hopper (1927)
What it shows: a young woman in a green coat and cloche hat sitting alone at a round table in an automat, one glove off, a cup of coffee in front of her, and behind her a black plate-glass window in which two receding rows of ceiling lamps are the only thing reflected. Why it is sad: nothing has happened and nothing is going to. An automat was a self-service restaurant where food came out of coin-operated compartments, so there is no waiter and no one to talk to, and Hopper gives the window no street, no passers-by, no city, just the lamps running off into the dark. The model was his wife Jo, as it was for almost all his women. It was first shown in New York in 1927. Where it is: the Des Moines Art Center, Iowa.
10. Ivan the Terrible and His Son Ivan by Ilya Repin (1883 to 1885)
What it shows: the tsar on his knees on a red carpet, eyes huge, clutching his son to his chest and pressing a hand over the wound in the young man’s temple, a bloodied staff on the floor beside them. Why it is sad: the painting’s subtitle gives the date, 16 November 1581, when, according to the chronicle tradition Repin followed, Ivan struck his heir in a rage and killed him. Repin said he was moved to paint it by the assassination of Alexander II in 1881 and by hearing Rimsky-Korsakov’s music, and that he wanted a moment of horror followed by remorse. Alexander III banned it from exhibition for a time. It has been attacked twice, slashed with a knife in 1913 and struck with a metal pole in 2018, and restored both times. Where it is: the State Tretyakov Gallery, Moscow.
11. The Execution of Lady Jane Grey by Paul Delaroche (1833)
What it shows: a blindfolded girl in white satin kneeling on straw, groping for the block, while an elderly man in fur guides her hands toward it; the executioner waits with his axe, and two ladies-in-waiting collapse against a pillar behind. Why it is sad: Jane Grey was proclaimed queen in July 1553 and deposed nine days later in favour of Mary Tudor; she was sixteen or seventeen when she was beheaded at the Tower of London in February 1554. Delaroche moved the scene indoors and dressed it like a stage, and the detail everyone remembers is the hands reaching for a block she cannot see. Shown at the Paris Salon of 1834 it was the sensation of the year. It was believed destroyed in the Thames flood of 1928 that damaged the Tate’s stores, and was found rolled up and largely intact in 1973. Where it is: the National Gallery, London.
12. Ophelia by John Everett Millais (1851 to 1852)
What it shows: Shakespeare’s Ophelia floating on her back in a stream, mouth open, palms up, her embroidered dress beginning to pull her under, with every plant on the bank painted leaf by leaf and the flowers she was gathering scattered on the water. Why it is sad: the moment is from Hamlet, act four, when Gertrude reports that Ophelia, driven mad by her father’s death, fell into the brook and sang until her clothes dragged her down. Millais painted the background over five months on the Hogsmill River in Surrey and the figure in his London studio, with the model Elizabeth Siddal lying in a bath heated by oil lamps underneath; the lamps went out, she caught a severe cold, and her father threatened to sue. The flowers carry meanings from the play: pansies for thought, violets for faithfulness, poppies for death. Where it is: Tate Britain, London.
13. Isle of the Dead by Arnold Böcklin (1883 version)
What it shows: a small boat approaching a rocky island of tall cypresses and tomb doors cut into the cliffs; in the boat stands a figure in white beside a coffin draped in white, and an oarsman rows them in. Why it is sad: the painting began as a commission. In 1880 a young widow, Marie Berna, visited Böcklin’s studio in Florence and asked for “a picture to dream by”; he added the boat, the shrouded figure and the coffin to a landscape he had already started, and she took it as a memorial to her husband. He painted five versions between 1880 and 1886 and gave none of them this title; his dealer did. This third version, from 1883, was bought by Adolf Hitler in 1933 and hung in the Reich Chancellery, which is part of why it is the best known. Rachmaninoff wrote a symphonic poem after it. Where it is: the Alte Nationalgalerie, Berlin; other versions are in Basel, New York and Leipzig.
14. Never Morning Wore to Evening but Some Heart Did Break by Walter Langley (1894)
What it shows: a young woman on a harbour wall in Newlyn, Cornwall, bent over weeping, with an old woman’s hand on her shoulder, the boats and the flat grey sea behind them. Why it is sad: the title is a line from Tennyson’s poem In Memoriam, and the picture needs no further caption: a fisherman has not come back. Langley was the first painter to settle in the Newlyn fishing village, in 1882, and he painted its women and its losses for the rest of his career, mostly in watercolour. This is one of his largest oils and his best-known picture. He hides the young woman’s face entirely and lets the older woman’s weathered face, which has seen this before, carry the picture. Where it is: Birmingham Museum and Art Gallery, which bought it in 1980.
15. The Death of Chatterton by Henry Wallis (1856)
What it shows: a red-haired young man in purple breeches and a white shirt lying dead across a narrow bed in an attic, one arm hanging to the floor, torn manuscripts on the boards, dawn coming up over St Paul’s through the open window. Why it is sad: Thomas Chatterton was a poet from Bristol who forged medieval verse under the name of an invented monk, moved to London, failed to make a living and died in a Holborn garret in August 1770, aged seventeen, from arsenic; the Tate’s label records the death and the age, and the picture gives no more detail than that. The Romantics made him the emblem of the neglected genius, and Wallis staged the garret in rooms at Gray’s Inn, a short walk from the Brooke Street attic where Chatterton died, using as his model the young writer George Meredith. Two years later Wallis ran off with Meredith’s wife. Where it is: Tate Britain, London; smaller versions are in Birmingham and at Yale.
16. Death and the Maiden by Egon Schiele (1915)
What it shows: a gaunt man in a dark robe and a woman in a crumpled orange dress clinging to each other on a white sheet spread over bare ground, his hand on her head, her arms locked round his back. Why it is sad: the man has Schiele’s face and the woman has the features of Wally Neuzil, his model and companion for four years. In 1915 he left her to marry Edith Harms, a middle-class neighbour, and proposed to Wally that they continue to meet for a holiday each year; she refused and never saw him again. She joined the Red Cross as a nurse and died of scarlet fever in Dalmatia in 1917. He died in the influenza pandemic in October 1918, three days after Edith. The painting was finished in the months after the break. Where it is: the Belvedere, Vienna.
17. Woman with Dead Child by Käthe Kollwitz (1903)
What it shows: a naked woman crouched on the ground, holding a small dead child against her face and chest so tightly that the two bodies read as one. It is an etching, not a painting, and it belongs on this list more than most paintings do. Why it is sad: Kollwitz posed for it in front of a mirror holding her seven-year-old son Peter, and wrote later that the boy groaned at having to keep still so long. In October 1914 Peter was killed in Flanders in the first weeks of the war, at eighteen, and she spent the next eighteen years making the memorial that now stands in the German war cemetery at Vladslo in Belgium. Her prints and sculptures from then on return again and again to a mother and a dead child. Where it is: impressions are in many collections; this one is in the Statens Museum for Kunst, Copenhagen.
18. Christina’s World by Andrew Wyeth (1948)
The painting is still under copyright and cannot be reproduced here; the photograph above shows the house in it. What it shows: a woman in a pink dress lying in a wide field of dry grass, seen from behind, propped on her thin arms and looking up a long slope toward a grey farmhouse and barn on the horizon. Why it is sad: the woman is Anna Christina Olson, a neighbour of Wyeth’s in Cushing, Maine, who had a degenerative muscular condition and refused to use a wheelchair, pulling herself across the ground with her arms instead; Wyeth saw her from a window crossing the field toward the house and painted the scene from that memory. She was fifty-five at the time, though the figure’s body was modelled by his wife Betsy. The Museum of Modern Art bought it the year it was painted for $1,800, and the house, now owned by the Farnsworth Art Museum, is a National Historic Landmark you can visit. Where it is: the Museum of Modern Art, New York.
19. The Wounded Deer by Frida Kahlo (1946)
The painting is still under copyright and is described here rather than shown. What it shows: a young stag with Kahlo’s own head, crowned with antlers, standing in a clearing among dead tree trunks, its body pierced by nine arrows and bleeding, with a stormy sea and sky in the gap between the trees and a broken branch lying in the foreground. Why it is sad: Kahlo painted it in 1946, the year she travelled to New York for a spinal operation that she hoped would end the back pain she had lived with since a bus accident at eighteen; the surgery did not help. The deer stands, as she said she did, upright and wounded at the same time. It is a small panel, about 22 by 30 centimetres, and she gave it as a wedding present to two friends, with a note saying she left them her portrait so that they would remember her. Where it is: a private collection in Houston.
20. The Old Guitarist by Pablo Picasso (1903 to 1904)
The painting is still under copyright in most of the world and is described here rather than shown. What it shows: a gaunt old man with a white beard sitting cross-legged on the ground, head bowed almost to his shoulder, bent over a brown guitar, the whole picture painted in blue except for the instrument. Why it is sad: it is the best-known painting of Picasso’s Blue Period, the three years after the suicide of his friend Carlos Casagemas in 1901 when he painted beggars, prisoners and the blind in Barcelona and Paris, nearly always in blue. The guitarist is blind, his clothes are rags, and the guitar, the one warm colour, is the only thing he has. X-rays and infrared photographs taken at the Art Institute of Chicago show the ghost of an earlier composition beneath, a seated woman and a child, painted over because Picasso could not afford new canvas. Where it is: the Art Institute of Chicago.
Frequently asked questions
What is the saddest painting ever painted?
There is no agreed answer, but three candidates come up more than any others. Munch’s The Sick Child, because it is a painter’s record of his own sister’s death. Van Gogh’s Sorrowing Old Man, because of when it was painted. And Kollwitz’s Woman with Dead Child, because the boy she held as the model was killed eleven years later. Readers who want the most openly tragic subject usually name Repin’s Ivan the Terrible or Delaroche’s Lady Jane Grey.
What is a famous painting that shows grief?
Kramskoi’s Inconsolable Grief is the clearest single image of mourning on this list, a widow in black beside the funeral flowers. Leighton’s Lachrymae shows grief at a graveside in the classical manner, and Langley’s Never Morning Wore to Evening shows it on a harbour wall. For a parent’s grief, Kollwitz’s etching is the one that is hardest to look at.
Who are some famous sad artists?
Edvard Munch and Vincent van Gogh are the two whose names are shorthand for it, and both appear twice above. Käthe Kollwitz made grief her subject for forty years. Egon Schiele and Frida Kahlo painted their own bodies and losses. Edward Hopper painted loneliness rather than grief, which is why Automat belongs here and his street scenes do not.
Why do sad paintings stay famous?
Partly because the stories behind them are easy to retell, and this list is built on those stories: a sister’s death, a widow’s commission, a poet dead at seventeen. And partly because sadness in a painting asks nothing of the viewer except attention. A happy painting is about its subject; a sad one is, very often, about you.
Image credits
The paintings reproduced on this page are in the public domain and are shown via Wikimedia Commons. Photographs of them that carry their own licences are credited as follows: The Sick Child, photograph by the Nasjonalmuseet, Oslo (CC BY 4.0); Death and the Maiden, photograph by Johannes Stoll for the Belvedere, Vienna (CC BY-SA 4.0); Woman with Dead Child, photograph released by the Statens Museum for Kunst (CC0). The photograph of the Olson House in Cushing, Maine, is by lcm1863 (CC BY-SA 2.0).