Churchill gave many of his paintings away as gifts (so although there are around five hundred-plus paintings by him known to exist, there are almost certainly more than this as records of these gifts weren’t always kept – and paintings still keep coming to light. President Roosevelt was only one such recipient. Presidents Truman and Eisenhower all received paintings from him, as did Viscount Montgomery, David Lloyd-George and US General George C. Marshall – as well as several young women in his family and social circle.

In the winter of 1935, on the recommendation of Sir John Lavery and other artist friends, Churchill travelled to Morocco for the first time for a painting holiday. He was inspired by the light and colours. He referred to the pink Atlas mountains as ‘paintaceous’ and painted some of his most refined watercolours – and one particularly skilled oil painting – here. He was entranced by the exotic, desert landscape and the colours – the pinks, whites and ochres contrasting with the brilliant blue of the desert sky. He gathered a large number of photographs on this and subsequent visits which still remain in the Studio archives at Chartwell.

Churchill didn’t only paint at Chartwell. His easel, brushes and paints accompanied him everywhere - while staying at homes of friends and family (at Hever Castle in Kent where he painted the colonnaded gardens, Breccles in Norfolk, the home of Clementine’s cousin where he painted the woods); on his holidays to the French Riviera (the Churchills rented a house in Cannes for six months in 1922); in Cairo (where he tackled painting the Pyramids), in Morocco, in America and Canada’s Rocky Mountains. Wherever he went, he took his painting paraphernalia. Churchill also painted at one of his favourite places, Blenheim Palace, where he was born and to which he regularly returned throughout his life. Churchill’s early skill with the brush can be seen in paintings completed at Mimizan in Les Landes, south of Bordeaux in France – an area protected from the Atlantic by massive sand dunes and pinewoods – where he stayed as the guest of his friend the Duke of Westminster who had a house there. Lavery, who later stayed at Mimizan with Churchill, painted the same scenes.

While supremely confident and self-assured in most fields of life, Churchill was generally modest about his achievements as a painter; he didn’t aspire to create masterpieces – he never claimed he had ever painted one – and didn’t intend to earn money from his pastime (unlike his other craft of writing). But he did have a certain ambition for his art. In 1921, only six years after he’d first tried his hand with a brush, he is said to have sold up to six paintings he’d exhibited in Paris under the pseudonym Charles Morin at Galerie Druet for the princely sum of £30.00 each. In 1947 he successfully submitted two paintings to the Royal Academy Summer Exhibition under the name David Winter (including ‘Winter Sunshine, Chartwell’, which had won a prize in 1927).

Churchill spent much of his leisure time at Chartwell, the house and grounds he bought in 1922 set in the rolling countryside of Kent. When he wasn’t bricklaying, building tree houses for the children or feeding his menagerie of animals, he spent much of his time painting, particularly in his ‘wilderness years’. His studio at Chartwell is today much as it was when he was alive and many of his paintings can be seen on its walls. He generally preferred light and colour and, when the weather wouldn’t comply and he couldn’t paint out of doors, he often resorted to still-life studies of fruit, bottles and glassware (hence ‘Bottlescape’, his painting of a range of drinks and glasses, both full and empty.) His nephew Peregrine has said that Churchill, on receiving a large bottle of brandy for Christmas, sent his children round the house looking for other bottles to put alongside it, for a still life. Peregrine told Richard M. Langworth, the editor of , that Churchill said: ‘Fetch me associate and fraternal bottles to form a bodyguard to this majestic container’ ().

Churchill sought and accepted constructive criticism – in the art of painting, at least – and enjoyed experimenting with new media and techniques. Sir John Lavery and his wife Hazel were not the only influences on Churchill’s painting style. During the 1920s, when he was Chancellor of the Exchequer, Churchill took advice on painting from Walter Sickert, who passed on his enthusiasm for Degas, Corot and Constable. As well as scrutinising the works of these painters, Churchill also carefully studied and absorbed the work of others; J. M. W. Turner, Camille Pissarro (whom Clementine had met in Paris), Paul Maze (the Anglo-French painter whom the Churchills called ‘Cher Maître’), John Singer Sargent (who had painted his mother’s portrait), the sea painter Julius Olsson and William Nicholson. Many of them visited Chartwell, where he did much of his ‘daubing’, and Paul Maze accompanied him on many of his painting trips.

Churchill’s articles on the pleasures of painting appeared in the in 1921 and 1922, netting him the handsome sum of £1000 (considerably more than his paintings would earn him in his lifetime, of course). Clementine was cautious: ‘I expect the professionals would be vexed & say you do not yet know enough about Art’. Mary, his daughter, later wrote that Clementine was ‘in principle opposed to Winston’s writing what she regarded as “pot-boilers” to boost their domestic economy’. But Churchill, the professional writer (and now passionate painter), prevailed; his articles were a great success, explaining vividly why such pleasure was to be found in painting. Painting also provided consolation and peace in times of despair and grief.

Before too long, rather than playing with his nephew’s watercolour paint-box, Churchill was tackling oil painting. On learning of Churchill’s experimentation and enthusiasm a near neighbour, Sir John Lavery, the renowned Anglo-Irish and official First World War artist, together with his talented artist wife Hazel, gave practical advice and help and encouraged this new hobby. Later in 1915, Churchill was often to be found working in Lavery’s studio in London, not far from the house Churchill and his brother Jack were sharing, with their families, on Cromwell Road. Churchill was to take his paints with him wherever he travelled – at home and abroad – throughout this life. Enthralled with his new hobby, he painted during the First World War while at the Western Front in early 1916 (as a Lieutenant-Colonel with the 6th Battalion Royal Scots Fusiliers), at ‘Plug Street’ (Ploegsteert) in Flanders. On his return from the First World War and during the 1920s, even when embroiled again in political life, Churchill continued to paint. In fact, painting intensified as a pleasure and it was at this time that he wrote two articles about it, praising the enormous rewards to be gained from painting as a pastime.

In 1915, during the First World War, Churchill helped orchestrate the disastrous Dardanelles naval campaign and the related military landings on Gallipoli, both of which saw enormous losses of life. As a result, Churchill found himself publicly and politically discredited. He was demoted to the token post of Chancellor of the Duchy of Lancaster. It seemed his political career was at an end. Devastated and despairing, Churchill retreated to a rented house, Hoe Farm, near Godalming, Surrey, with Clementine and the children. One day in June, his sister-in-law, Gwendeline (or ‘Goonie’), was painting in the garden and, seeing Churchill’s interest, suggested he try it himself. She loaned him her young son’s paint-box. So began one of his life’s passions. Churchill took to painting, at the age of forty, with his customary gusto, seeing it as his salvation from despair – ‘the Muse of Painting came to my rescue’. He continued to paint for the next forty years.