Jack B. Yeats, A Paris of the West / A Paris come to Judgment in the West, oil on canvas, 1944 (est. £500,000-800,000 / €565,000-905,000)

Appearing at auction for the first time in 35 years, A Paris of the West / A Paris come to Judgment in the West caused some excitement in the media when it was bought by the celebrated American theatre actress, Katharine Connell in 1948. In the painting, a boy peers up at three young women, silhouetted against a view of the sea on the Sligo coast. The title casts this unlikely character as Paris, the classical hero who was tasked with choosing who was the most beautiful of the goddesses, Hera, Venus and Athena. In this work, Yeats elevates a west of Ireland subject to the realms of antique Greek and Roman mythology, and pays homage to the grand tradition of European painting. Yeats is currently the subject of a landmark exhibition at the Irish Museum of Modern Art in Dublin, in which he is placed side-by-side with Lucian Freud for the first time in 70 years.

Jack B. Yeats (1871-1957), 'The Man in the Moon has Patience', oil on canvas, 1943 (est. £150,000-250,000 / €170,000-282,000)

Making its first appearance at auction, 'The Man in the Moon has Patience' is quite possibly a self-portrait of Yeats as a young man. The painting is being offered for sale by glassware designer Simon Pearce, whose father acquired the work directly from the artist. In an expansive landscape, perhaps the Skelligs or Killary Harbour in the West, a traveller wearing a broad-rimmed hat pauses to look up at the moon which lights up the night sky before him. Painted when in his seventies, Yeats is possibly reflecting upon his own journey and acknowledging the ever-presence of the moon, patiently observing and guiding him as he finds his way.

Roderic O'Conor (1860-1940), A Moonlit Breton Landscape, oil on canvas, circa 1898-1900 (est. £120,000-180,000 / €136,000-203,000)

The roots of this mysterious painting lie in the nocturnes O'Conor created during his first extended visit to Brittany. The moon has risen behind the curtain of trees, half glimpsed through patches of dark cloud whilst down below, in the foreground, a circle of figures seems to engage with a firework display or a lantern procession. Although the setting is rural and no buildings are visible, the subject is most likely observational, possibly painted en plein air, until the fading light demanded that the canvas be brought into the studio for completion.

In 2018, the first museum show in over 30 years to focus on the painted and graphic work of Roderic O’Conor was held at the National Gallery of Ireland in Dublin. Further works by O'Conor in the sale include Nude Reclining in an Armchair, oil on canvas, circa 1915-18 (est. £50,000-70,000 / €56,500-79,000).

Sir William Orpen (1878-1931), The Bar in the Hall by the Sea, Margate, oil on canvas, circa 1907-08 (est. £100,000-150,000 / €113,000-170,000)

William Orpen's oeuvre consists of many exceptional interior paintings that demonstrate his keen sense for composition, atmosphere and his aptitude for rendering decorative elements. This painting, which has remained in a private collection since 1947, richly evokes the fading glamour of the The Hall­by-the-Sea in Margate. The venue occupied a disused railway station and was turned into an entertainment complex by 'Lord' George Sanger in 1874. Today nothing of the splendid ballroom of Orpen's day still exists except perhaps the shell. Orpen picks out the ornate details of the bar with flashes of light, from the mirrors and bar taps to the flamboyant sculpture in the foreground. The artist’s presence is suggested in the long coat and hat which rest on the bar, with a bottle and glass to the left.

Paul Henry (1876-1958), Clare Island from Achill, oil on canvas (est. £80,000-120,000 / €90,500-136,000)

This superb painting by Paul Henry is emerging in the public eye for the first time in nearly a century, having been purchased by Geoffrey Thomas Taylour, 4th Marquess of Headfort and his wife, Rose, who was a celebrated 'Gaiety Girl' at the Gaiety Theatre in London. The artist’s decision to spend a fortnight's holiday in summer 1910 on the rugged Island of Achill was a momentous one – he would settle there for the next decade, enchanted by island and islanders alike. Warily christened with the nickname 'Sketcher' by Achill's inhabitants, he would rove the island in search of scenes to paint. Here, he looks south towards nearby Clare Island. Henry’s evocative light and painterly approach can be attributed to some extent to a short yet formative period spent in Paris at the turn of the century. On arriving on the west coast of Ireland, he put his Parisian education into practice, seeing the landscape with a wholly modern eye and forging an avant-garde style that was at once distinctly Irish.

Louis Le Brocquy (1916-2012), Image of Samuel Beckett, oil on canvas, 1987 (est. £60,000-80,000 / €68,000-90,500)

In this iconic example from le Brocquy’s Portrait Heads series, Image of Samuel Beckett, the artist aimed to discover, or uncover, ‘aspects of the Beckettness of Beckett’. Sotheby’s currently holds the auction record for one of le Brocquy’s Portrait Heads series, achieved in 2007 for a painting of Beckett. The sale includes a further work, Image of James Joyce, painted in 1977 (est. £60,000-80,000 / €68,000-90,500). Both are appearing at auction for the first time.

Rowan Gillespie (b.1953), Failing Better maquette III, signed bronze, 2019 (est. £15,000-20,000 / €17,000-22,600)

This sculpture relates to Failing Better which was recently installed at the Pierce Street entrance of Trinity College Dublin. Of the three maquettes the artist made, this is the largest. In conducting his research for the work, Rowan Gillespie developed an interest in Trinity College Dublin's curious connection to aviation, particularly the flying experiments of George Francis FitzGerald in the late 19th century. The sculptor was drawn to the concept of inspired vision inching towards success through a series of failures; his flying machine is a horse which develops wheels and then propellers, though will never fly. Gillespie’s ascendancy on the auction market has seen prices far surpass their estimates, with Sotheby’s holding the current auction record for a bronze sold in 2015.

Hughie O'Donoghue (b.1953), The Owl Run, oil on canvas, 2013 (est. £15,000-25,000 / €17,000-28,200)

The Owl Run depicts a field near the Glencullen River where O’Donoghue’s mother grew up and where the artist visited every year as a child. Like much of his work, rather than making descriptive or topographical landscapes, the real subject of the painting is the reconstruction of experience and remembering of place. The artist remembers the Owl Run as a mysterious and magical place from his childhood, while the bird's flight is meant to represent the mental or imaginative travel of the individual.

Further contemporary highlights include: Janet Mullarney (b.1952), Mirroring, bronze, 1998, unique within an edition of 9 (est. £8,000-12,000 / €9,100-13,600); Joy Gerrard (b. 1971), Flag (Protest against Brexit, London, June 2018), Japanese ink on linen, 2019 (est. £5,000-7,000 / €5,700-7,900); and Brian Harte, Interior, with Figure, oil on canvas, 2019 (est. £5,000-7,000 / €5,700-7,900).