Three paintings by Lucian Freud — each marking a pivotal moment in his career

Sitting for a portrait by Lucian Freud was an intense process.

Each of Freud’s many sitters had a different experience. The important thing for the artist was that they connected with him in some way. Part of the reason he liked to paint friends, family and lovers rather than professional models, he said, was that the latter had ‘grown another skin, because they’ve been looked at so much’.

Freud also turned his gaze upon himself a great deal across his career — like Rembrandt, producing self-portraits from youth through to old age. He worked from a mirror, and said that he found these paintings among his greatest artistic challenges.

‘I don’t accept the information I get when I look at myself,’ he said. ‘That’s where the trouble starts.’

On 15 October 2025, three major works by Freud — two portraits and one self-portrait — are being offered in the 20th/21st Century: London Evening Sale at Christie’s. Woman with a Tulip, Sleeping Head and Self-portrait Fragment come from the same private collection, none of them having appeared on the market for more than 30 years.

Freud painted them in a period between the 1940s and the 1960s, and each work marks a pivotal moment in his career.

Self-portrait Fragment, circa 1956

In Self-portrait Fragment, the artist’s face materialises amid open space. His skin’s complexity is explored with nuanced colour. Each shadow, furrow and gleam is precisely captured and animated by the brushwork’s texture.

Painted in 1956, during the breakdown of Freud’s second marriage, to Lady Caroline Blackwood, the work might be seen as an image of dissolution. The artist touches four fingers to his face as if to verify his own presence.

Self-portrait Fragment encapsulates a marked shift in Freud’s technique in the late 1950s. Where before it had been crisp, graphic and exacting, now it was growing more intricate and richly worked, thanks in part to his substitution (under Francis Bacon’s influence) of finely pointed sable brushes for coarse hog’s-hair ones. This approach would become increasingly pronounced in the years and decades ahead.

With his painting hand pressed to his cheekbone, Freud records a moment of contact, as if in awe at the union of paint and flesh. Echoing Caroline Blackwood’s pose in the double portrait Hotel Bedroom (1953-54) — begun on the couple’s honeymoon in Paris — it is perhaps also a gesture of farewell.

Freud’s oeuvre contains a number of fragmentary works. They comprise almost a third of the self-portraits recorded in the catalogue raisonné of the oil paintings, which was published earlier this year. Other examples include Self-portrait (Fragment) (circa 1985), in the National Portrait Gallery’s collection in London, and Self-portrait (Fragment) (circa 1986), which was sold at Christie’s in 2023.

In his introduction to the catalogue raisonné, Toby Treves wrote of Self-portrait Fragment: ‘We might imagine that, as he painted [it], the shock of the discovery so frightened him that he stopped work on the picture, as if he’d heard the sound of breathing come from the figure emerging on the canvas.’

Woman with a Tulip, 1944

In 1944, Freud was in the midst of another ill-fated relationship: with Lorna Wishart (née Garman), the subject of Woman with a Tulip. An image of intense emotion, it captures her in the crisp and graphic style of the artist’s early years.

She meets our gaze from the other side of what appears to be a table. On it rests the cut head of a red tulip. Much later in life, Freud described Wishart as ‘the first person who meant something to me’, and the work carries the symbolic charge of an icon painting or Renaissance miniature.

In November 1944, it was included in the artist’s debut one-man show, at the Lefevre Gallery on London’s New Bond Street. It was shown there again in a 1946 group exhibition, alongside works by artists including Ben Nicholson, Graham Sutherland and Francis Bacon.

The critic Maurice Collis singled out the painting for its extraordinary power: ‘a tiny portrait by Lucian Freud, the youngest of the young men here, shows remarkable skill. He may turn out the most gifted.’

Freud and Wishart met in the summer of 1942, when Freud was 19 and she 31. A married woman, Wishart was the youngest of seven Garman sisters who — in the words of their biographer Cressida Connolly — ‘lived at the centre of European literary and political life between the two World Wars and numbered some of the greatest artists and writers among their husbands, friends and lovers’.

Wishart had an immediate impact on Freud’s work and psyche. His friend and fellow artist John Craxton described her as ‘the most wonderful company, frightfully amusing and ravishingly good-looking’. For Freud, he said, ‘she was a muse, a true muse in the best possible way’.

In Woman with a Tulip, Freud seems hypnotised by Wishart’s large, dark blue eyes. He painted the work on an intimate scale, on panel, and the tulip has clear romantic connotations.

The couple’s relationship was under strain at the time. Freud would soon begin an affair with the actress Pauline Tennant. He and Wishart separated in 1945: that year, he made his only other painting of her, Woman with a Daffodil. In 1948, her niece, Kitty Garman, would become Freud’s first wife.

Sleeping Head, 1961

The work’s unknown subject — whom Freud met in a Soho bar shortly after returning from a holiday in Greece in 1961 — lies on a leather sofa, at ease in the artist’s presence.

Closely cropped and viewed from below, her face is an expanse of broad, sweeping strokes that are rich in colour, light and movement.

‘As far as I’m concerned, the paint is the person — I want it to work for me just as flesh does,’ the artist said. The picture embodies the completion of Freud’s shift from the precise handling of his early years to the looser, richer, more painterly surfaces of his work from the turn of the 1960s onwards.

Freud completed Sleeping Head unusually swiftly, across six or seven sittings, and the assurance of the artist’s hand is palpable. He saw it as a crucial painting, later saying it was ‘one of the few I did very fast: I couldn’t work now if I hadn’t worked in that way.’ The process had unlocked a new confidence.

The image heralds the full-length nudes — or, as he called them, ‘naked portraits’ — which the artist began to paint later in the 1960s, and which would become a fundamental part of his oeuvre.

In his monograph on Freud from 1982, the British art historian Lawrence Gowing called Sleeping Head ‘an unforgettable picture’, adding that ‘the artist’s nudes… were expansions of [it]’.

The three works coming to auction have been part of major Freud exhibitions worldwide. Self-portrait Fragment and Woman with a Tulip were included in Lucian Freud: New Perspectives, held at London’s National Gallery in 2022 to mark the centenary of the artist’s birth (this later transferred to the Museo Nacional Thyssen-Bornemisza in Madrid).

Sleeping Head appeared in the landmark touring retrospective, Lucian Freud: Paintings, held at the Hirshhorn Museum and Sculpture Garden (Washington, D.C.), the Musée National d’Art Moderne (Paris), the Hayward Gallery (London) and the Neue Nationalgalerie (Berlin) between 1987 and 1988.

On the occasion of that exhibition, Robert Hughes declared Freud ‘the greatest living realist painter’. John Russell went further, saying rather that he was ‘the only living realist painter, and the one who has given back to realism an element of risk and revelation that had long been forfeited’.

Together, these three works offer a fascinating look at the artistic evolution of one of Britain’s greatest figurative painters, and at the private life that inspired it.

Led by the 20th/21st Century: London Evening Sale on 15 October 2025, Christie’s 20th/21st Century Art auctions take place in London and online, 8-21 October. Find out more about the preview exhibition and sales

Related artists: Lucian Freud