20th Century Greats: Best Books by Winston Churchill and George Orwell

When George Orwell was born in 1903, a young Winston Churchill had just begun building a career for himself in politics; his “finest hour,” as Prime Minister of Britain during the Second World War, was still some thirty years to come. By the end of Orwell’s brief life, Churchill had become, along with Hitler and Stalin, among the most important figures of the 20th Century.

The last thing Orwell published before his death in 1950 was a review of the second volume of Churchill’s memoirs of the war, writing that he admired Churchill’s “largeness and geniality,” his courage, and his commitment to fighting totalitarianism in all forms. The previous year the writer had lent Churchill’s name to the sympathetic figure of “the last man” in his dark political satire 1984. At the time of his death, Orwell was beginning to receive recognition as a writer and social critic, but he couldn’t have known he would one day rank as important a figure as Churchill in the preservation of democracy and freedom in modern history.

  • The cover of the book Churchill and Orwell

    Churchill and Orwell

    The Fight for Freedom

    Yet, as Thomas Ricks writes in his new dual biography, Churchill and Orwell: the Fight for Freedom, the two figures were equally critical to their century, and had either of them not existed, the world might look very different now. While today Churchill’s dogged refusal to capitulate during the war seems a foregone conclusion, it was hardly an overwhelmingly popular position at the time. And while Orwell’s anti-authoritarian novels and essays are widely admired for their clear-eyed prescience about the dangers of absolute power, he struggled for years to get his novels published and his ideas respected. Both men were tremendous writers – Churchill, who won the Nobel Prize in 1953, as much in his public addresses as memoirs; Orwell in his novels, essays, and reviews. Below are some of their best-known publications.

  • The cover of the book 1984


    Before Big Brother was a reality TV show, it was the name of the all-seeing, all-knowing, all-powerful government entity in Orwell’s 1949 dystopian novel of political power gone amuck. Propaganda, revisionist history, thought police, mind control through mass entertainment, ubiquitous surveillance, political doublespeak – the only thing missing is the phrase ‘alternative facts,’ but that concept, like much of the current cultural landscape, is eerily predicted by the novel.

  • The cover of the book Why I Write

    Why I Write

    “I had a facility with words and a power of facing unpleasant facts,” Orwell writes with characteristically precise understatement in the title essay of this collection. Not only do the collected pieces here explain why he writes, but why it is important for all of us to strive to read, write, and think as clearly, unsentimentally, critically, and humanely as he did over the course of his career, facing unpleasant facts and determining to bring the truth to light in the hope of making life better for others.

  • The cover of the book Animal Farm

    Animal Farm

    It sounds so simple: all animals are equal. But what happens when some animals decide they’re more equal than the others? In this satirical novel about the dangers of Communism, Orwell imagines what happens when the workers revolt – and the workers happen to be pigs, sheep, horses, and cows. At first all is bliss, but soon human – or, make that, animal – nature takes over, and greed, malice, corruption, and lust for power make the workers’ paradise a hell on earth.

  • The cover of the book Blood, Toil, Tears and Sweat

    Blood, Toil, Tears and Sweat

    The Great Speeches

    Churchill was a gifted and inspiring orator – and he better have been, because often during the war his words were all he had. Orwell paid him a high compliment when he said that Churchill wrote like “a human being,” not “a public figure,” considering what Orwell thought of most public figures. Just as Orwell’s novels gave us memorable phrases, Churchill introduced “iron curtain,” “business as usual,” and “summit meeting,” along with the Yogi Berra-esque “this is not the beginning of the end. But it is, perhaps, the end of the beginning.” In this collection, read the speeches that inspired the country to “never, never, never give up.”

  • The cover of the book Memoirs of the Second World War

    Memoirs of the Second World War

    In this abridged version of Churchill’s six-volume epic, the leader describes the years leading up to the war, the conflict, and its aftermath. In 1940, Churchill was a newly-elected Prime Minister when Hitler invaded France. He told Parliament: “the Battle of France is over. I expect that the Battle of Britain is about to begin.” In these memoirs, he writes about fighting, and ultimately winning, that battle, not just for Britain, but for the free world.

  • The cover of the book My Early Life 1874-1904

    My Early Life 1874-1904

    Thirty years separated Winston Churchill and George Orwell. In this memoir, Churchill accounts for those first three decades. He describes his privileged Victorian childhood, his academically lackluster schooldays at Harrow, his struggle to get into the military, the early appeal of politics, and his time in South Africa reporting on the Boer War. Throughout, a strong sense of justice and a bone-deep appetite for perseverance in the face of adversity help him triumph, setting the stage for the greater tests to come.