The great face off: 16 of the most wonderful portraits ever painted

Searching, wondering and staring eyes
Self-Portrait of Suffering by Ibrahim El-Salahi, 1961
The African modernist El-Salahi studied at the Slade in London in the 1950s and western modernism clearly influenced him. El-Salahi’s work has often delved into the personal and here we see him in a confused, uncertain state of mind. I am reminded of the gaping mouth of Munch’s Scream, or the bull in Picasso’s Guernica, given the equine nature of the face. The hair is manic but orderly, coiled and framing deep, endless concentric circles of eyes – searching, wondering and staring somehow both at us and into the abyss. Portraits at the precipice of melancholy or mania are the most attractive to me. They are honest and human. Aindrea Emelife

Messy domestic moments
Sid James by Ruskin Spear, 1962
This collage captures both the funny and sad: how life is made up of grand aspirations and messy little domestic settings. We watch comedian Sid James on TV in Hancock’s Half Hour, but also see what looks like an invitation to the opening of a Henry Moore exhibition, a CND flyer, as well as adverts for remedies for colds, flu and rheumatism on the coffee table. Maybe we’ll just stay in by the telly. Alison Smith

‘I’m a grown-ass woman’
Sadie (Zadie Smith) by Toyin Ojih Odutola, 2018-19
This new commission will be shown for the first time at the National Portrait Gallery when it reopens on 22 June. Zadie Smith is one of the greatest literary voices of our time and Toyin Ojih Odutola is one of the most exciting artists, so this work is the perfect pairing. It’s also the first work by Toyin to enter a British public collection. As Smith said: “I know her art will have a tremendous effect on young people because I’m a grown-ass woman and it’s had a tremendous effect on me. Becoming familiar with her images is like having something I missed and wanted in childhood delivered to me now, as an adult. And to be a Toyin creation myself, on the walls of the portrait gallery? It’s incredible.” Nicholas Cullinan, NPG director

‘I see my own family in this’
Bonnie Greer (“Portrait d’une Negresse”) by Maud Sulter, 2002
One of my favourite portraits at the National Portrait Gallery is part of the Reframing Narratives exhibition, which celebrates female artists and sitters. It’s Bonnie Greer (“Portrait d’une Negresse”), by Maud Sulter. This photograph pays homage to Marie-Guillemine Benoist, an 18th-century French artist who uplifted black female figurative art during a time of slavery. As I gaze at Sulter’s portrait, I can’t help seeing my own family reflected in the image: my mother, my aunts, my grandmother. It is a powerful representation of the women who have shaped my life. What resonates is its sense of growth and empowerment. Sulter captures the essence of female strength and reimagines it through the giving of a name and the act of clothing the subject. It signifies the reclaiming of identity and the celebration of womanhood. Violeta Sofia, artist and photographer

A mother’s sheer desperation
Migrant Mother, Nipomo, California by Dorothea Lange, 1936
Some portraits are a window into the souls of their subjects. Others tell the story of a time or place. This iconic portrait of Florence Owens Thompson is both. It has become a touchstone image of 20th-century America, immediately evoking the gritty desolation and human cost of the Great Depression. Lange made the portrait, currently showing in Capturing the Moment at London’s Tate Modern, while an employee of the US government – she was one of many artists who were paid to document the realities of the Depression as part of New Deal programmes. So while this conveys a mother’s sheer desperation, it is also a reminder of a time in which artists were important enough to include in the most far-reaching welfare programme in US history. It’s hard to imagine the same decision being made today – but the magnetism of this portrait lives on. Eliza Goodpasture

Who has the winning hand?
The Domino Players by Errol Lloyd, 1986
When Errol Lloyd was asked to contribute to Caribbean Expressions in Britain, a 1986 show at the Leicestershire Museum and Art Gallery, the Jamaican-born artist immediately submitted the title, medium, dimensions – and then set about finding sitters. But Lloyd wasn’t sure where to find a group of domino players in his suburb of London. He finally found a pub of largely white clientele who pointed upstairs, where the Black patrons played. In Lloyd’s scene, the sepia tones give it a historical mood while the use of actual dominos adds realism. The young are pitched against the elders in a nevertheless unifying game. With a close reading, you can see which player has the lucky hand and therefore the right to slam the winning piece on to the table with exuberance and gusto. A warm memory and a feeling of togetherness for many West Indians, at home and abroad. Rianna Jade Parker

‘She inspired my first novel’
A Bar at the Folies-Bergère by Édouard Manet, 1882
I vividly remember the first time I saw this glum-looking barmaid. I was studying and feeling glum myself. The thing that got me was her expression: pink cheeks, pressed-together lips, heavy eyes. I tried to work out how she was feeling and settled on sad, tired, stuck, the kind of lonely that can gnaw even in a crowd. Stranded behind the bar of a popular Paris establishment, she’s both seen and unseen, present and absent. To me, the greatest portraits tell us something intimate about the sitters and ourselves. Manet’s model, called Suzon, inspired my first novel. She’s been with me since we met. Chloë Ashby

Fearless and freaked out
You or Me by Maria Lassnig, 2005
I don’t have a favourite portrait – it all depends on circumstance – but this is too good to miss. A gun to her head, another aimed at the viewer: Lassnig’s You or Me is self-portraiture as Mexican standoff. Painted in 2005, when the Austrian painter and film-maker was 85, this pitches us into confusion. Lassnig is both fearless and freaked out. You or Me is violent, ferocious and comical, dramatising the confrontation not only between subject and viewer, but also between painter and portrait. It is an infinity loop, a short circuit, and there’s no way out. Lassnig didn’t give a damn. Adrian Searle

He has holy hair but is not the messiah
Self-Portrait at the Age of 28 by Albrecht Dürer, 1500
A young printmaker and painter from Nuremberg depicts himself in this unsettling masterpiece as a Christ-like mystic gazing at you from strange realms of prophecy and insight. Everyone who sees it for the first time thinks this is a painting of Jesus, because Dürer flirts with that possibility as he lovingly details his long holy hair and beard and inscribes his age in gold letters: 28, not far off Christ’s when he died. But he is not the messiah, he is an artist, which in Dürer’s eyes may amount to the same thing. This is the first self-portrait that ever asserted the mystery of artistic genius, the melancholy danger the artist confronts in a heroic search for beauty and truth. Behold Albrecht! Jonathan Jones

‘A rock for me to cling to’
Self Portrait Exaggerating My Negroid Features by Adrian Piper, 1981
I was in my early teens when I saw this incredibly striking image. It made me think of ancient Egyptian portraits, with those wonderfully focused, forward-gazing eyes. It’s rendered beautifully in just pencil and charcoal, but there was something about the way the eyes drew you in – a psychological meeting. Then I looked at the title. As a person who is read as Black but is mixed race, it threw up a moment of recognition – about the fiction of racial categories and the absoluteness of what people want things to be. In that moment of gazing at myself in that character, I realised that the assumptions some people made about me weren’t true. It’s just a small drawing, made in the year I was born, but it has such power. It felt like a rock in a sea to cling on to. Someone had created an image that ruptured the strictness of those attitudes to race. I felt seen. Thomas J Price, artist and sculptor

No angels to welcome the soul
The Death of Marat by Jacques-Louis David, 1793
This is an extraordinary portrait. Jean-Paul Marat, the French Revolution’s propagandist-in-chief, is obviously dead, shown stabbed in the bathtub he bathed in to ease a skin condition. It’s this “here and now” focus that led art historian TJ Clark to call it the first modernist artwork. Although the artist probably worked from the corpse, he used religious and classical tropes to cast the assassinated agitator as a secular martyr. The unheroic end becomes a Christ-like pietà swoon, the nudity that of Greek warriors, yet half the painting is of darkness, without Christianity’s heavenly angels to welcome the soul. It’s a contemplation of how a man creates his own significance. Skye Sherwin

A natural and fresh paradox
Self-portrait in a Straw Hat by Élisabeth Louise Vigée Le Brun, 1782
In this self-portrait, the artist knows you know you’re looking at her – and she is knowingly looking at you. Yet, paradoxically, both sides know she made this image by looking in a mirror, the better to narcissistically capture herself. It’s the revenge of the painted object: a woman constructing herself as beautiful on her own terms. She depicts herself both as personification of painting and as unaffectedly natural and fresh: face gently shaded, chest luminous, hair unpowdered (unlike that of her patron, Marie Antoinette), breasts uncorseted (unlike this picture’s inspiration, Rubens’s portrait of Susanna Lunden). And yet everything in this wonderful portrait is artifice. Stuart Jeffries

Resilience staring down brutal pain
The Two Fridas by Frida Kahlo, 1939
“Like a ribbon around a bomb,” said the surrealist André Breton of Frida Kahlo’s work, which he saw in Paris a year before she painted this, her great dual self-portrait. Kahlo was in her early 30s and becoming an international celebrity, but at home in Mexico her marriage to Diego Rivera had fallen apart. The Two Fridas confronts these linked realities: on the right, her whole-hearted Mexican self cradles a miniature portrait of Rivera; on the left, European Frida tries in vain to stem the flow of blood from her shattered ventricles with forceps. Their joined hands reinforce the defiance with which they stare the viewer down. Kahlo’s resilience in the face of brutal emotional and physical pain was never more powerfully expressed. Claire Armitstead

Turning the tables
Bernardino Campi Painting Sofonisba Anguissola by Sofonisba Anguissola, c1559
Staring out at us are two figures: a man in a dark suit and a woman in a thick crimson dress. He’s painting her, a portrait, dictating her appearance, as he gazes back at us, his eyes not quite meeting our gaze while her glassy eyes pierce our view. But take a second look at the caption and you realise the painting is not by him, but by her: Sofonisba Anguissola, his pupil. Not only has she painted herself one and a half times as big as him, she has him painting the embellishment of the jacket – a task normally assigned to an apprentice. Now look even closer and you’ll see her left hand – a third hand – guiding his around the canvas. Katy Hessel

A land wrecked by colonial capitalism
The Coffee Worker by Candido Portinari, 1939
Maybe I’m attracted to this work because the story of Candido Portinari’s family resonates with my own: poor workers who fled Italy for a better life. His parents ended up on a coffee plantation in Brazil, where Candido was born in 1903, and where he bore witness to the life of the immigrant poor and the legacy of slavery, then only two decades abolished. This painting is particularly striking, not just as a portrait of hardship (the mournful facial expression, the lilac tones) and heroism (the homoerotic, bulging physique), but also for its portrayal of the extractivist nature of colonial capitalism in the wrecked land that rolls out behind the worker. Oliver Basciano

In his arms or hooked to a machine?
How Will I Die? #2, from The End: A Meditation on Death and Extinction by Judy Chicago, 2015
If portraiture allows artists to give something or someone immortality, it’s intriguing that Judy Chicago decides to use the medium to imagine herself in her final moments. How Will I Die? is a series of eight paintings of Chicago in different death scenes – in the arms of her husband, hooked up to a machine, screaming in pain. In this, the artist is naked and curled up in the foetal position with “Will I leave as I arrived?” written above her. It is vulnerable and harrowing, but there is power in Chicago’s use of portraiture to test out scenarios and therefore maintain agency before a terrifying inevitability. Hannah Clugston

• The National Portrait Gallery, London, reopens on 22 June