Holiday was born in London. He showed an early aptitude for art and was given lessons by William Cave Thomas. He attended Leigh's art academy (where a fellow student was Frederick Walker) and in 1855, at the age of 15, was admitted to the Royal Academy. Through his friendship with Albert Moore and Simeon Solomon he was introduced to the artists Dante Gabriel Rossetti, Edward Burne-Jones and William Morris of the Pre-Raphaelite Brotherhood. This movement was to be pivotal in his future artistic and political life.
In the same year, 1855, Holiday made a journey to the Lake District. This was to be the first of many trips to the area, where he would often holiday for long periods of time. Whilst there, he spent much of his time sketching the views which were to be seen from the various hills and mountains. He wrote, "For concentrated loveliness, I know nothing that can quite compare with the lakes and mountains of Westmorland, Cumberland and Lancashire".
Holiday worked in both oils and watercolours. In 1858, his first picture, a landscape painting, was exhibited at the Royal Academy and immediately sold; from that year his work was frequently shown at the Academy and elsewhere. Other pictures include:
Holiday spent much time at the studios of Sir Edward Burne-Jones, where groups of artists would meet to discuss, exchange and pool ideas. The influence of Burne-Jones can be seen in Holiday's work.
In 1861, Holiday accepted the position of stained glass window designer for Powell's Glass Works, after Burne-Jones had left to work for Morris & Co. During his time there he fulfilled over 300 commissions, mostly for customers in the United States. He left in 1891 to set up his own glass works in Hampstead, producing stained glass, mosaics, enamels and sacerdotal objects.
Holiday's stained glass work can be found all over Britain. Some of his best is at the chapel of Worcester College, Oxford (c.1865); Westminster Abbey (the Isambard Kingdom Brunel memorial window, 1868); St Luke's Church, Kentish Town; St Mary Magdalene, Paddington (1869); and Chartered Accountants' Hall, Moorgate. In 2018, four of his stained-glass windows were reinstalled in Chartered Accountants' Hall after being lost for almost 50 years following their removal for an extension in 1970.
Holiday also created some sculpture, in 1861 producing a piece called Sleep which attracted favourable critical interest.
Holiday worked for architect William Burges for a period, including providing wall and ceiling paintings for Worcester College, Oxford (1863–64) and furniture paintings – including Sleeping Beauty for the headboard in the bedroom – at Burges's London home, The Tower House. The Sleeping Beauty bed is now in the collection of the Higgins Art Gallery & Museum, Bedford. Holiday has four oil paintings in British national public collections.
In 1867, Holiday visited Italy for the first time and was inspired by the originality of the Renaissance artists he saw on display there. In 1871 he went to Ceylon as part of the "Eclipse Expion". His astronomical drawings were subsequently published in the national press and attracted great interest.
On his return to England in 1872, he commissioned architect Basil Champneys to design a new family home in Branch Hill, Hampstead, which was named "Oak Tree House". In 1888, William Gladstone was a visitor.
In January 1874, Holiday was commissioned by Lewis Carroll to illustrate The Hunting of the Snark. He remained a friend of the author throughout his life. Holiday's illustration to the chapter The Banker's Fate might contain pictorial references to the etching The Image Breakers by Marcus Gheeraerts the Elder, to William Sidney Mount's painting The Bone Player, and to a photograph by Benjamin Duchenne used for a drawing in Charles Darwin's The Expression of Emotions in Man and Animals.
From 1899, Holiday worked with Jessie Mothersole as studio assistant and she remained closely associated with the family until Holiday's death. In 1906 Holiday gave Mothersole a drawing of his daughter Winifred, which later was acquired by the British Museum.
In 1907, Holiday went to Egypt, painting a series of watercolours and illustrations on ancient Egyptian themes. These were exhibited at Walker's Gallery, London, in March 1908 jointly with Mothersole who had been working on Egyptian archaeological drawings and watercolours since 1903/4. In 1907–08, he commissioned the building of a holiday home, Betty Fold, in his favourite part of the Lake District.
Between 1912 and 1919 he painted the apse of the east end of St Benedict's Church at Bordesley, Birmingham, depicting Christ in Glory with angels, and saints in arcading, below, in Byzantine style.
Holiday had been a socialist throughout his life and, together with his wife Kate and daughter Winifred, supported the Suffragette movement. The family were close acquaintances of Myra Sadd Brown and Emmeline Pankhurst and her daughter, and had organised local suffragette meetings in the Lake District.
Holiday died on 15 April 1927 in London, two years after his wife, Kate. His nephew, Gilbert Holiday (1879–1937), son of Sir Frederick Holiday, was also an artist who also has paintings in British collections.
Holiday's 'The Bride and the Daughters of Jerusalem' (1861-3) has also disappeared, but the study (1982,0515.22) clearly reflects the influence of Rossetti and Burne Jones.
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