Cultural depictions of Winston Churchill

• Winnie (1988) – Robin Hardy (premiere run in 1988)^[3]
• Never So Good (2007) – Ian McNeice (premiere run in 2007)
• Turning Point (2009) – Matthew Marsh
• Three Days in May (2011) – Warren Clarke (premiere run in 2011)
• The Audience (2013, London) – Edward Fox (replacing Robert Hardy, who withdrew prior to press night for health reasons)
• The Audience (2015, Broadway) – Dakin Matthews
• Sylvia (2018) – Delroy Atkinson
• When Winston Went to War with the Wireless (2023) – Adrian Scarborough^[4]

• The Kinks recorded "Mr. Churchill Says" for their 1969 album Arthur.
• The YouTube series Epic Rap Battles of History featured Dan Bull as Churchill in its fifth season; Churchill battled against Theodore Roosevelt, played by EpicLLOYD.^[5]
• Iron Maiden included parts of Churchill's famous speech "We shall fight on the beaches" in live versions of the song "Aces High" from the 1984 album Powerslave.
• Supertramp included parts of Churchill's famous speech "We shall fight on the beaches" in the song "Fool's Overture" from the 1977 album Even in the Quietest Moments....
• "Oliver's Army" by Elvis Costello
• "Stop the Cavalry" by Jona Lewie

• Peter Sellers included Churchill as his standard PM for The Goon Show. Churchill is depicted as he was during World War II. In The Goon Show, he is of course treated humorously, having a very African foreign secretary called Basil (played by Ray Ellington in Red Bladder mode). In addition he is responsible for supporting Neddie Seagoon's harebrained plans for long-range, jet-propelled guided NAAFI's, atomic dustbins, and throwing batter puddings at Clement Attlee.
• Churchill's Other Lives, documentary series, played by Roger Allam (2011)

• H. G. Wells, in his 1933 novel The Shape of Things to Come – a forecast of the future as it seemed to Wells on the basis of the 1934 situation – assumed that Winston Churchill's career was over and that he would have no active role to play in the Second World War, which Wells foresaw as breaking out in 1940, lasting until 1950 and culminating in the collapse of all parties to the conflict and a breakdown of European civilization. Wells assumed that Randolph Churchill, Winston's son, would take part in a valiant but doomed effort to avert the war, delivering a "brilliant pacifist speech [which] echoed throughout Europe", but failed to end the war.^[6]
• The protagonist of George Orwell's 1949 novel Nineteen Eighty Four is named Winston Smith. He is mentioned as being about forty years old in 1984, i.e. he was born in the last years of WWII and presumably was named for Winston Churchill.^{[citation needed]}
• Churchill is a significant character in the 1995 novel Redemption by Leon Uris
• Players, a 1999 Doctor Who novel by Terrance Dicks^[7]
• The Hundred-Year-Old Man Who Climbed Out the Window and Disappeared (2012)
• Churchill is mentioned in the Grandpa's Great Escape, 2016 by David Walliams

There are various alternative history works depicting a Nazi German victory or an otherwise widely different course of WWII posit various ultimate fates for Churchill:

• In Len Deighton's 1978 SS-GB, Churchill refuses to escape Britain even when Nazi victory is certain. He is captured by the Nazis and executed, at his last moment defiantly making the V for Victory sign. In Len Deighton's 1981 XPD A group of former SS officers attempt to seize power in West Germany, in which they intend to publish some wartime documents about a secret meeting between Churchill and Hitler in June 1940.
• In James P. Hogan's 1985 The Proteus Operation, Lord Halifax cravenly surrenders to the Nazis without fighting. Churchill, holding no official position of any kind, organizes some of his neighbors for a foredoomed defiance, confronting the German soldiers who arrive in their countryside with an assortment of shotguns and all of them getting killed. Time travelers from a bleak world of the 1970s return to 1939, contact Churchill and Roosevelt and provide information enabling them to do better and defeat the Nazis, creating the history we know.
• In Leo Rutman's 1990 Clash of Eagles, Churchill escapes via the Bahamas. When the Nazis follow up their conquest of Britain with an invasion of the US, occupying New York City and much of the East Coast, the exile Churchill urges the Americans to go on resisting.
• A similar role is given to Churchill also in the Nazi-dominated 1960s of Robert Harris' 1992 Fatherland. Churchill and most of the British royal family escape to Canada where he leads a Government in exile.
• In Harry Turtledove's Worldwar series (1994–2004), in 1942 Extraterrestrials invaded Earth, forcing humans to stop fighting each other and unite to face the common threat. Churchill managers to beat off a large scale Extraterrestrial invasion of Britain, but must concede the reptile invaders – who prefer warm climates – in permanent occupation of most of the British Empire.
• Harry Turtledove's Southern Victory series (1997–2007) is based on an earlier diversion from the history we know – the Confederacy winning the American Civil War and from 1862 becoming a fully recognized sovereign nation. In this history, the Entente is defeated by the Central Powers in the First Great War of 1914–1917. In 1935, the Conservatives led by Churchill go into coalition with the Silvershirts and by 1941, they declare war on a Germany still ruled by a Kaizer. Under these circumstances, Churchill ends up in an uneasy alliance with a Hitler-analogue – Jake Featherston, demagogue dictator of the Confederacy, who is involved in a wholesale genocide of Blacks.
• In Harry Turtledove's 2003 In the Presence of Mine Enemies, Churchill and the remnants of the British Army resist to the bitter end, ultimately falling to defeat, though the exact circumstances of Churchill's death are undescribed.
• In Harry Turtledove's The War That Came Early series (2009–2014), elements in Neville Chamberlain's government are receptive to Rudolf Hess's proposal that Britain stop fighting the Nazis and rather join them in a war against the Soviet Union. When Churchill, the war minister, objects, he is killed in a suspicious car accident.
• In Newt Gingrich and William R. Forstchen's 1995 1945, Germany did not declare war on the US in 1941. In 1945 two separate wars end, the US victorious against Japan but the Nazis victorious in Europe. Britain remains unoccupied but its situation is precarious. In 1946 Churchill faces a land invasion of Britain, headed by Erwin Rommel, and bombings much more severe than the 1940 London Blitz, and is desperately begging for American help
• Winston's War (2002) – Michael Dobbs
• Never Surrender (2003) – Michael Dobbs
• Churchill's Hour (2004) – Michael Dobbs
• Churchill's Triumph (2005) – Michael Dobbs
• In Jo Walton's Farthing (2006) Rudolf Hess's flight to Scotland in May 1941 manages to successfully negotiate peace terms with the United Kingdom, mainly because the United States never gets involved with the conflict, this is because Imperial Japan never attacks Pearl Harbor, resulting in Churchill being removed from office and the British Empire pulling out of the war.
• In C. J. Sansom's 2012 Dominion, in the 1950s in which the Nazis occupy Great Britain through a puppet government, an ageing Churchill is leader-in-exile of the British resistance movement.
• In Philip K. Dick's The Man in the High Castle (1962) Where the Axis Powers won World War II. The story occurs in 1962, fifteen years after the end of the war in 1947, and depicts the political intrigues between Imperial Japan and Nazi Germany as they rule the partitioned United States. The Grasshopper Lies Heavy, by Hawthorne Abendsen, the story within the story, United Kingdom contributes more to the Allied war effort, leading to joint British and Russian forces capturing Berlin, the British Empire becomes militaristic, anti-American post war, and begins a cold war against the United States that the empire eventually wins, Churchill remains Prime Minister until his death.
• In Guy Saville's The Afrika Reich (2011) the United Kingdom is defeated by Nazi Germany during the Dunkirk Campaign, Churchill resigned, Lord Halifax becomes Prime Minister and signs a non-aggression pact with Germany ending the war.
• In Guy Walters' The Leader (2003), King Edward VIII never abdicates, marries Wallis Simpson, leading to Oswald Mosley winning the 1935 election, allying the United Kingdom with the Axis powers. Churchill and other anti-Nazi politicians are imprisoned on the Isle of Man.
• In Murray Davies Collaborator (2004) Nazis conquer the United Kingdom and the Irish Free State, Churchill along with the British Royal Family flee to Canada where he leads a government in exile.
• In Philip Kerr's Hitler's Peace (2005) Adolf Hitler, realising he is going to lose the war, tries to negotiate peace with Franklin D. Roosevelt, Joseph Stalin, Churchill refuses to listen and will only accept unconditional surrender.
• In Mike Resnick's alternate history anthology Alternate Tyrants (1997). In the short story "Children of Tears" by Adrienne Gormley After Boer uprisings in South Africa during World War II, Churchill imposes extreme measures throughout the British Empire with special attention being given to suppressing Indian nationalists such as Mohandas K. Gandhi, Jawaharlal Nehru, and Vinoba Bhave.
• In Kim Newman's The Bloody Red Baron (1995) Count Dracula is Supreme Commander of the Central Powers armies during World War I, Churchill who is a vampire in the world, is a member of Lord Ruthven's cabinet.
• In John Birmingham Axis of Time trilogy, a US-led multinational task force of advanced warships and submarines in 2021 deployment, the Nagoya conducts a full-scale test of its new systems but there is a catastrophic accident—the experiment generates a massive rift in the time-space continuum, destroying the Nagoya and sending most of the fleet back in time to 1942. In the second novel, Designated Targets (2005), Churchill prepares for "Operation Sea Dragon," an attempt to invade across the English Channel. Despite heavy losses sustained by the RAF and the damage to Biggin Hill, the Germans lost most of their navy. Any airborne units that reach England are quickly isolated and crushed by the Allies.

• The 2012 Summer Olympics opening ceremony featured an animated version of Churchill's statue in Parliament Square, which James Bond and the Queen fly over in a helicopter: as they salute him, he raises his cane in response. It also featured an appearance from Timothy Spall as Winston Churchill.
• Churchill was featured in Ubisoft's Assassin's Creed: Syndicate as an ally to Lydia Frye.
• Churchill was supposed to appear in the 1941 film Citizen Kane with Charles Foster Kane during the News on the March sequence but was cut due to runtime.
• A paperweight likeness of Churchill, based on a portrait by Dora Marr, was produced in a limited number by Baccarat in 1954.^[8]
• Churchill is one of the main characters in the webseries Super Science Friends. He assembles a team of famous scientists to win World War II. He is voiced by Adam Shaheen.
• A fictionalised Churchill appeared in the Strike Witches series.
• Doctor Who: The Churchill Years is a series of audio drama released by Big Finish Productions, Ian McNeice reprises his role as Churchill from the TV show.
• Churchill is currently being portrayed by British actor David Payne in a solo performance tour in the United States.^[9]
• Churchill appears as a playable leader in Civilization, appearing as a playable character in scenarios related to World War II.^[10]