Winston Churchill

Sir Winston Churchill was the only British Prime Minister to win the Nobel Prize in Literature. While world-famous for his wartime leadership, he was also a remarkably colorful, eccentric, and resilient individual.

Escape and Early Adventures
Prison break hero: In 1899, while working as a war correspondent in South Africa, his armored train was ambushed and he was captured. He escaped the prison camp by scaling a wall at night, hid in a mineshaft for three days, and hitched a ride on a rail truck hidden under wool to make it to safety.

Accident-prone survivor: Churchill survived an astonishing number of near-death experiences. He suffered a severe concussion and ruptured kidney jumping off a bridge as a teen, nearly drowned in a Swiss lake, survived two plane crashes, and was hit by a car while crossing Fifth Avenue in New York because he looked the wrong way.

Academic struggler: He didn’t excel in school and famously failed the entrance exam to the Royal Military College, Sandhurst, three times before finally passing.

Eccentric Habits & Hobbies
Prolific painter: To escape the stresses of politics, he took up painting and produced roughly 500 artworks in his lifetime. He even successfully submitted art to the Royal Academy under the fake name “David Winter”.

Card-carrying bricklayer: He loved physical labor and built large stone walls and a cottage by hand at his Chartwell estate. He even officially joined the Amalgamated Union of Building Trade Workers as a professional bricklayer.

The “siren suit” inventor: Long before modern onesies existed, Churchill designed a one-piece zip-up jumpsuit called a “siren suit” that he could quickly pull on over his pajamas during nighttime air raids.

Cigar obsession: He kept a rotating stash of over 3,500 cigars at home. His signature “Bulldog scowl” in his most famous 1941 portrait was actually because the photographer boldly snatched the cigar out of his mouth right before taking the picture.

Political & Pop Culture Legacy
Chart-topping leader: He is the only British Prime Minister to ever enter the UK music album charts. Collections of his wartime speeches set to music entered the top 10 twice—once in 1965 and again in 2010.

Half-American roots: His father was a British politician, but his mother, Jennie Jerome, was an American socialite from New York. Churchill was later named the first-ever honorary citizen of the United States.

Bored to the end: When he finally passed away at the age of 90, his reported final words to his family perfectly captured his pragmatic nature: “I am bored with it all.”