The following year, 1899, Robert Henri had four pictures accepted at the prestigious Champ-de-Mars Salon in Paris, and was later honoured when the French government bought one of these works, 'La Neige', for the Luxembourg gallery in Paris. Henri was one of only a handful of American artists to be represented at the Luxembourg, and the purchase enhanced his growing reputation in the U.S. and Europe. He returned to the States and continued to teach. In 1905 his wife Linda died after a series of illnesses, including a miscarriage. Robert Henri married again three years later to an Irish-born student, Marjorie Organ. Henri was 42 when he married the 22-year old Marjorie. At this time Robert Henri was busy establishing an independent artists exhibition in New York, in protest at the conservative selection policy of New York's National Academy of Art. Henri was one of the most high-profile members of this new group of eight artists, who were linked not so much by their artistic style as by their attitude. The group, which came to be known variously as 'the eight', 'the Ashcan school' and 'the New York realists', chose as their subjects the poorest people in American society, the manual labourers, immigrants and slum dwellers.
In 1909 Robert Henri was introduced to the Irish artist John Butler Yeats. The father of writer W.B. Yeats and the painter Jack B. Yeats, J.B. Yeats was in New York to promote his son's poetry. The two men got on well and in December of 1909 Robert Henri painted a portrait of J.B. Yeats. Henri also gave his studio in New York to be used as the venue of a lecture by J.B. Yeats at which the poetry of W.B. Yeats was read as well as extracts from J.M. Synge's recently released play 'The Playboy of the Western World'. Synge had written the Playboy, which is based in north Mayo close to Achill Island, after famously being told by W.B. Yeats in Paris to go to the west of Ireland and 'express a life that has never found expression'. It is not clear whether J.B. Yeats was also instrumental in encouraging Robert Henri to visit the west of Ireland. Other factors that may have induced him to make the journey included his wife Marjorie, who had never returned to her native Dublin since emigrating with her family, and the fact that Henri's great-grandmother had been Lady Fingall of Killim Castle. Whatever the reason, the Henris did indeed make the journey to Ireland, arriving at Achill Island in July 1913.
The Henris soon moved from their original residence at the Slievemore Hotel, Dugort, to Dooagh in the west of Achill Island. They rented Corrymore House, the former residence of the notorious landlord Captain Boycott. Robert Henri found in Achill a culture similar to the Breton rural and peasant way of life at Concarneau. While he did try to paint something of the landscape it was the people that appealed to him most as subject matter for his art. The Henris struck a friendship with Brian O'Malley, a former employee of Capt. Boycott, who would accompany them on walks in the mountains and regale them with tales of the island. Brian O'Malley was also a close acquiantance of Paul Henry, who by this time had been living and painting on Achill since 1909. Despite their shared profession and shared acquiantances, there is little evidence to suggest that Robert Henri and Paul Henry actually met during Henri's 1913 visit to Achill.
Robert Henri had no shortage of subjects willing to pose for him at Corrymore House. As well as food and refreshments, the 'models' were also paid for their time by Henri. He favoured painting the children of the nearby villages of Dooagh and Keel, and the childless Henris were particularly kind to the Achill children, playing them music on their vitrola and Marjorie feeding them peanut butter and jam sandwiches. Robert Henri had a number of favourite models, including Mary O'Donnell who was captured in the 1913 portrait 'Achill Girl'. Two other favourites were Johnnie and Biddy Cummings, an elderly couple who lived opposite The Pub in Dooagh. Robert Henri painted two famous portraits of Johnnie and Biddy, titled 'Himself' and 'Herself', as well as the portrait of Johnnie Cummings titled 'Old Johnnie'. The following year Henri was awarded the Carol Beck Gold Medal in the U.S. for his portrait 'Herself'. When he heard news of the award, Robert Henri reportedly hurried to "write this news to the dear old lady in Ireland".