Every portrait that is painted with feeling is a portrait of the artist, not of the sitter.

(Oscar Wilde, Portrait of Dorian Gray)

It is unfortunate that Michelangelo, Leonardo, Raphael and Titian, living and working around the same time in the same country, were not friends; we could have inherited great portraits of one another, and we would know today what they really looked like. Instead, they were consumed by animosity and rivalry, competing for lucrative and prestigious commissions. That didn’t prevent them from admiring, criticising and borrowing freely from each other.

Etchings based on self-portraits by Leonardo and Raphael are the only images we have of these masters; while Titian painted a self-portrait in 1562, when he was in his 70s. It is only of Michelangelo, more interested in and skilled at self-promotion that real portraits by contemporaries are available today. According to the great art historian Giorgio Vasari (1511-1574), “Of Michelagnolo there exist but two painted portraits, one by the hand of “il Bugiardino” and the other by Iacopo del Conte, and one in bronze relief made by Daniello Ricciarelli”.

Il Bugiardino (“the little liar”, meant affectionately, I guess, and based on his surname rather than his character) refers to the painter Giuliano Bugiardini. He was one of Michelangelo’s few friends, maybe because Michelangelo considered him a "good person but a simple man” and did not regard him as a threat professionally, although he was a painter of great sensitivity and skill.

The portrait on which many later ones are based is by Iacopo del Conte, a portraitist attentive to detail who painted Michelangelo in 1535 when the master was about 60 years old, though he looks older. Later historians attribute this portrait to il Bragettone, and date it to 1545. Daniello Ricciarelli (born in Volterra) was known as il Bragettone, “the breeches maker”, due to his most famous job, painting loincloths and fig leaves over the genitals of the naked figures in Michelangelo’s Last Judgement in the Sistine Chapel. A painter and sculptor, da Volterra was a member of Michelangelo’s fan club, a pupil and a friend. The magnificent portrait bust was made from Michelangelo's death mask.

Impressionist colleagues

The impressionists often worked and travelled together, and it is not surprising that they also painted each other’s portraits. Among them, Vincent van Gogh is the most painted artist of all, mainly by himself: there are dozens of self-portraits, with hat, with pipe, with bandaged ear. We are familiar with this three-quarter view, which he had to adopt in order to keep glancing at the mirror.

His fellow painters seem to view and portray him quite differently. Considered the most accurate likeness is the 1886 portrait by Australian impressionist John Russel. Evidently influenced by photography, Russel’s portrait of Van Gogh in a striped blue suit is painted in a realistic style, although including some subtle impressionistic touches. Van Gogh liked this portrait, which apparently had the dedication “Vincent, in friendship”.

Like Russel, Toulouse-Lautrec met Van Gogh at Fernand Cormon studio. His colourful chalk drawing (1887) shows Vincent in profile sitting at a table in a café (possibly Café du Tambourin, owned by his mistress Agostina Segatori). There is a glass of absinthe on the table in front of him, not an infrequent occurrence, as by then Vincent was, by his own admission, nearly an alcoholic.

Apart from the self-portraits, the most familiar image of Van Gogh is The Painter of Sunflowers by Gauguin (1888). Here Gauguin captures the essence of Van Gogh. The composition of the portrait is unconventional, with the subject against the right edge of the canvas and the easel on the left. The closest to the centre is the painter’s hand, holding the brush: that is the actual subject of the painting.

Van Gogh was an accomplished portraitist. As well as dozens of self-portraits, he painted old men and boys, young and old women, postmen and prostitutes. Fellow painters appear not to inspire him. But the distinctive face “like a razor blade” of Belgian painter Eugene Boch moved Vincent to paint him “just as he is, as faithful as I can”. It is a poetic portrait, Bosch's yellow jacket and pale face shining bright against a deep blue night sky. Van Gogh called the painting The Poet.

The tradition friends portraitising each other continued: Edgar Degas and Mary Cassat, Salvador Dalí and Pablo Picasso, Francis Bacon and Lucien Freud among others. And according to Dalí:

The reason some portraits don't look true to life is that some people make no effort to resemble their pictures.

The colour of love

Amadeo Modigliani’s style of portraits is instantly recognisable from the elongated figures and almond shape eyes. Inspired by African art, the portraits betray sensitivity, an empathy with the model that moves the viewer. His relationship with Beatrice Hastings, “La Poetesse Anglaise” is well documented, no least by the many images of her captured by Modigliani during their time together 1914-16. His most important muse, his lover and mother of his daughter was the painter Jeanne Hébuterne, better known for being Modigliani’s model and companion. More than 20 portraits, painted from 1918 until their death, show a young, delicate girl, with auburn hair and a long neck. The painter and the rather shy model had a relationship that lasted until his death, despite the age difference and opposition from her catholic family. Jeanne painted at least one portrait of Modigliani, showing the artist in a relaxed, dreamy pose, wearing a dark hat and tie (always the dapper dresser). In January 1920 Modigliani succumbed to tuberculosis; the day after, Jeanne threw herself from a fifth-floor window, killing herself and their unborn second child.

The pattern of older, successful painter and shy, talented but unfulfilled wife in his shadow was broken by this most famous of artist couples: Diego Rivera and Frida Kahlo. For over 25 years, through marriages and separations, despite the age gap and the infidelities, love endured. Physically they couldn’t be more mismatched: she was small and delicate, he was nearly a foot taller and three times her weight, which led her mother to refer to the marriage (to which she was opposed) as that between an elephant and a dove. Frida’s depiction of their marital bliss is showing the couple looking rather awkward together, despite the pink ribbon above her head declaring “Here you see us, me, Frida Kahlo, with my dearest husband Diego Rivera”. It’s not only the fact that he is so much bigger, his feet not just larger, but ten times the size of her dainty shoes peeking out from under the rich green skirt. Although she painted this double portrait, he is the painter, as indicated by the palette and brushes in his hand. His other hand is maladroitly holding his wife’s. Most bizarrely, they are not gazing into each other’s eyes lovingly; they are not looking at each other, or at the viewer.

Their subject matter was so different: he was the politically committed painter of large, government-sponsored murals; Frida was introverted, sensitive and sensual, depicting her dreams, anxieties and pain. In one of the few portraits of his wife, Rivera has tried to capture the wild spirit of the woman behind the eyebrow: the judging stare, the determined features emerging from out of shifting blue to green background, the gold of her shirt and oversize earrings, the soft colour of her cheeks, the penetrating stare of an icon (1939).

When Frida included the likeness of Diego in her paintings, it was as her child, her lover, herself. In the 1943 self-portrait as Tehuana, also referred to as Diego on my Mind Frida’s head is surrounded by the white lace of the traditional Mexican costume. On her forehead, there is an image of Diego, his shoulders resting on her famous eyebrows, like a third eye. And he is in her thoughts and on her forehead again a few years later, when the artist is not afraid of showing the suffering caused by the slow death of their relationship, with tears shining on her face (Diego and I, 1949). Love hurts.