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What is the fascination in art history with portrait sitters holding skulls? Ghoulish, startling and unsettling, artworks across history feature sitters holding a human skull. Many of us have seen artworks like this before – yet their impact today is sometimes lost. Thanks to pop culture, disassociation with the viscera of human remains can lessen the shock for us when we see a skull.

Consider though, throughout history, this wasn't always the case. To encounter a skull was to face mortality full force. Lifespans were substantially shorter than ours today, and with limited medical care, death was pressingly brutal. It's worth reflecting that if a skull unsettles us today, the impact in history would have been far more immediate. Memento mori – the inevitability of death in art, literally 'remember death' or 'remember you will die' – is a powerful genre that bloomed intensely in the Middle Ages and beyond.

Man with a Skull by the Master of the Annunciation to the Shepherds is an extraordinary and sometimes overlooked piece. The brutal and textured depiction defies immediate recognition as being from the seventeenth century in style.

Man with a Skull

Man with a Skull 1630–1640

Master of the Annunciation to the Shepherds (active 1630–1660)

Museums Sheffield

Muted tones and dramatic lighting shift the focus directly to the two heads, one living one dead. Hands clutch at the skull with intensity – we see tension and blood flow in the fingers demonstrating force. The skull itself is weathered and toothless, the light gleams softy from an exposed ridge effortlessly marking density and tone in the bone.

It's startling to compare this to the living head – sunken eye orbits and shadows hide the eyes echoing the skull, whilst loose flesh reveals the bone structure beneath. Broken blood vessels in the nose and flush on the cheeks show us life animating the face. He radiates a delicate vitality whilst maintaining a deadly balance to the skull. The man is rendered vulnerable by the skull, his mortality, strength and frailty pictured with intensity. In this magnetic and unflinching memento mori he literally faces death.

The detailed skull is exquisitely rendered, most probably from life, given the accuracy. Here we experience the powerful emotions at play – the skull is unavoidably a reminder that this was once a person, who, like the sitter, was formerly flushed with warmth and strength.

Portrait of a Man Holding a Skull

Portrait of a Man Holding a Skull c.1610–1614

Frans Hals (c.1581–1585–1666)

The Barber Institute of Fine Arts

In seventeenth-century western art, finding a skull to paint was far easier than today. The quick access to human remains is echoed in the ready acceptance to picture and see death in the period.

Packed ossuary houses would have contained huge collections of bones in local churches that lacked any marker or identity. Graveyards routinely reopened graves due to a lack of space, and newer burials smashed through earlier ones, scattering their bodies.

Memento Mori Tomb Carving of a Skull

Memento Mori Tomb Carving of a Skull 16th C–17th C

unknown artist

Royal Albert Memorial Museum

Ancient pre-Christian grave sites continued to be discovered, removed or – occasionally for the rich – became cabinets of curiosity. Seventeenth-century ethics on handling human remains are far removed from ours today, with theology instead a key driver in their use for moral teaching on piety.

Other seventeenth-century depictions continue the theme.

John Bankes (d.1630)

John Bankes (d.1630) 1625

British (English) School

The Chequers Trust

Anxious and uncomfortable-looking men like John Bankes (died c.1630, pictured by an unknown artist from the British School) clutch at the skull meaningfully. Again, the flush of life (or perhaps poor health) is seen in the face, while the body is shrouded in wealth.

Later in the century, another John – this time the famous poet Evelyn languishes romantically over a skull.

John Evelyn

John Evelyn 1648

Robert Walker (1599–1658)

National Portrait Gallery, London

Made to accompany a treatise on marriage for his wife, he originally held a medal of her likeness. This was subsequently painted over with a skull. The memento mori becomes a deliberate and sombre addition after the fact. As life changes, art reaches for the skull as the most immediate symbol of loss.

Death and the Maiden

Death and the Maiden c.1570

British (English) School

Shakespeare Birthplace Trust

In this painting, titled Death and the Maiden from c.1570, the insertion of the skull is very literal – a stern-faced elder holds the skull behind a youthful and fashionable lady enjoying music. She is forced to see her reflection in a moment of perceived carefree happiness, violently contrasted with mortality. Her 'vanity' is interrupted by an intervention reminding her of the value of modesty in face of death. Sixteenth- and seventeenth-century audiences were in no doubt about the power of the skull in art and their lives.

Moving forward in time, the Victorians interpreted and expanded this trend in art. The age of science embraces the skull in art with no less vigour, as seen in John Collier's portrait of Thomas Henry Huxley (1825–1895).

Thomas Henry Huxley

Thomas Henry Huxley 1883

John Collier (1850–1934)

National Portrait Gallery, London

Huxley here is the genial man of learning, propped up by an expansive book collection and casually holding a human skull. We find Huxley in a curated pose of thought, promoted by the skull. A noted nineteenth-century biologist, he specialised in comparative anatomy and was largely self-taught. He would have been familiar with human remains and worked to popularise their study from a scientific rather than religious standpoint.

Sometimes called 'Darwin's Bulldog' for his support on evolution and progressive science, Huxley is consciously framed in the memento mori style by Collier. The emphasis shifts from faith to science, yet the imagery remains, as does its power – amplified perhaps in that this was painted in an era where grave-robbery for science was well documented.

This leads us to question our contemporary reaction to the artwork – how do we process the skull and concepts of mortality in art today?

Andy Warhol becomes an unlikely entry in the genre of memento mori. Famous for his pop art commentary on society, Warhol's vision on holding the skull is equally as stark as seventeenth- and nineteenth-century offerings.

Self-Portrait with Skull

Self-Portrait with Skull 1978

Andy Warhol (1928–1987)

National Galleries of Scotland

In Self-Portrait with Skull, the artist stares at us in shock. His reaction can be ready in a variety of ways. Perhaps here we are seeing real fear and vulnerability? Perhaps instead we see a deliberate caricature of fear and shock at the skull's appearance on his shoulder? Dark horror with blood-drenched tones gives way in turn to campy and kitsch in the deliberate fake skull and its proportions.

Death and mortality were a very real presence in Warhol's life. In 1968 writer Valarie Solanas attempted to murder Warhol. The artist survived, though he suffered long-term health problems as a result. As with the seventeenth-century pieces, the skull becomes a functioning tool for the artist expressing memento mori, with a characteristic pop art twist. The skull is no less potent here as with the seventeenth-century works, yet interestingly the anatomical accuracy of the skull is not used. A pastiche skull perhaps says more about the society we live in now.

Peter (Monkey with Skull)

Peter (Monkey with Skull) 2013

Julian Warren

University of Bristol

As our relationship to memento mori changes in art history, death is perhaps harder to talk about as a result. How can we use memento mori today?

Each sitter we have looked at holding a skull offers a possible solution in their characterisation. They are framed as very much alive, more so in our consciousness, as contrasted to the death they are holding. The flush of life becomes more poignant and beautiful in the artists' hands.

Reframing conversations around death as being aware of life is a powerful alternative, and one that offers hope in challenging times.

Jon Sleigh, freelance arts educator