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Winston Churchill joined the British army in 1893 and developed a keen interest in war correspondence. Some of his early literary works were reports on various military campaigns. This led Churchill to work as a war correspondent for The Morning Post, in which he was to cover the occurrences of the Anglo-Boer War in South Africa. Soon after his arrival in South Africa, he accompanied a scouting expedition on an armored train.
Watch: Gary Oldman Plays Winston Churchill in âDarkest Hourâ Trailer. Gary Oldman is already drawing Oscar buzz for his portrayal of British Prime Minister Winston Churchill in next yearâs Darkest Hour, which got its first trailer this week. A nearly unrecognizable Oldman plays Churchill at the outset of World War II. âWe shall defend our island, whatever the cost may be!â a defiant Churchill bellows in the trailer. âWe shall fight on the fields and in the streets, we shall fight in the hills.