Coolest Whiskey Drinkers in History

Whiskey is one of the world’s most popular drinks and is enjoyed by many types of people.  Over the years, various artists, musicians, actors, and politicians have revealed they enjoy drinking whiskey regularly. We asked who they thought were the coolest whiskey drinkers in history and this is what they said:


Frank Sinatra

It’s harder to find anyone cooler than ol’ blue eyes.  Frank Sinatra was a legendary singer and actor who was incredibly popular throughout the 20th Century.  He had many musical hits including unforgettable tracks like New York New York, My Way, and Fly Me to the Moon.

Sinatra was known for his impeccable sense of style.  He would always dress immaculately, often wearing tailored pin-striped suits or custom-made tuxedos.  The combination of his debonaire appearance and velvety smooth voice made him one of the coolest cats of the 20th-Century.

Frank was a big fan of Jack Daniel’s Tennessee Whiskey and drank it regularly.  Jack Daniel’s even released a special bottle in honor of Sinatra, called Sinatra Select.


Sir Winston Churchill

When it comes to big drinkers, they don’t get much bigger than Winston Churchill.   He was a well-known day drinker during his time as prime minister of England — however, he rarely drank to excess and even had contempt for people who would become drunk.

Winston would drink a heavily diluted glass of Johnny Walker Red Label during the day, which his children referred to as a Papa Cocktail.  Churchill is considered one of the coolest drinkers in history because he was one of the “unbreakable” leaders who led the Allies to victory in WWII.


Mark Twain

Mark Twain is an American literary hero who was born in the great state of Missouri.  Twain wrote many incredible books including The Adventures of Tom Sawyer.  He was known to love his bourbon and was once quoted as saying “Too much of anything is bad, but too much good whiskey is barely enough.”

Twain was also a fan of Scotch whiskey, having been introduced to it during a trip across the Atlantic on the liner SS City of Chester.  He would spend most evenings drinking Scotch whiskey cocktails with the ship’s doctor.  His favourite cocktail was a combination of Scotch whiskey, lemon, sugar, and Angostura bitters.  Twain claimed the mixture improved his digestion and sex drive. Later in life, he would often choose bourbon or Scotch mixed with some hot water.


Ava Gardner

Whiskey isn’t just popular with gentlemen — the ladies love it too.  One of the coolest female whiskey drinkers was Ava Gardner. Ava was a famous movie star in Hollywood during the 1940s, 50s, and 60s.  Her beautiful looks and elegant style helped her land many lead roles in movies like The Hucksters, Show Boat, and On the Beach.  Ava loved a tipple and was once quoted as saying she hoped to die with a whiskey in her hand.


W.C. Fields

American actor, comedian, and writer W.C. fields drank whiskey regularly.  He made one of the funnier remarks about whiskey — “Always carry a flagon of whiskey in case of snakebite and furthermore always carry a small snake.”


Johnny Carson

Johnny Carson was best known for hosting the wildly successful The Tonight Show Starring Johnny Carson.  He was an incredibly talented actor and comedian who enjoyed a long career in show business.  Carson had a reputation for being witty, stylish, and clever. His love for whiskey was well known and he was quoted as saying “Happiness is having a rare steak, a bottle of whiskey, and a dog to eat the rare steak.”


Errol Flynn

Errol Flynn was a legend of the silver screen who starred in many classic movies including Captain Blood, The Perfect Specimen, Edge of Darkness, and Dive Bomber.  He loved drinking whiskey and was quoted as saying “I like my whiskey old and my women young.”


Sir Compton Mackenzie

Mackenzie was an English-born Scottish writer who wrote many famous plays, biographies, novels, and poems. They included a novel called Whiskey Galore, about a ship wrecked on an island during WWII with fifty thousands barrels of whiskey on board.  The book documents the battle that the islanders have to hang on to their “water of life”. According to Compton: “Love makes the world go round? Not at all. Whiskey makes it go round twice as fast.”

Written by CelebMix