Greatness and cigars have always gone together, so it’s little surprise that some of the most influential and popular figures throughout history have a carefully cultivated smoking habit. From the moment King Edward VII proclaimed, “Gentlemen, you may smoke”, famous cigar smokers have been making a name for themselves as politicians, performers, authors, inventors, and more.
Whether you’re just beginning your appreciation of this fine pastime or the proud owner of the best humidor money can buy, it’s nice to know you’re in great company.
With that in mind, here, in no particular order, are the 10 most famous cigar smokers of all time.
Winston Churchill is perhaps THE cigar smoker among famous cigar smokers. During his term as the Prime Minister of England, he led his country through one of the world’s most significant military events, and he did it all with a cigar between his teeth.
Churchill apparently smoked 8 to 10 cigars a day, making cigar manufacturers all but obligated to name a cigar size after him. The Churchill has been in circulation since between 1956 and 1952. The exact date remains one of speculation in cigar circles.
King Edward VII
Queen Victoria’s reign ended in 1901 and with it went her notorious tobacco intolerance. This was thanks mostly to her successor, King Edward VII, himself an avid cigar smoker.
Edward’s pro-cigar stance was well established by the time of his coronation. In 1866 he went so far as to quit his London gentlemen’s club over its non-smoking policy to establish his own, pro-smoking alternative.
John F. Kennedy
John F. Kennedy is famous for signing the 1962 embargo prohibiting any Cuban products from entering the United States, and yes, that included the world-renowned cigars.
Not as many know that Kennedy regularly smoked Cuban cigars himself, both before and after the ink was dry on the papers halting Cuban trade. This is because 24 hours before he put pen to paper, he ordered his press secretary, Pierre Salinger, to round him up 1,000 Petit Upmanns. Salinger came through like a trooper, scrounging up 1,200 cigars.
Cuban tobacco remains off-limits to Americans to this day.
Though Fidel Castro quit smoking in 1985, his name is still synonymous with cigars. A 44-year long pastime will do that.
Castro is most famous for his cigar hoarding during his efforts to topple the Batista regime. Anticipating those moments, though infrequent, when he’d run out of cigars, he took to hoarding his last smoke, only lighting up to console himself over a loss or celebrate a victory.
Mark Twain is best known for penning the literary classics The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn, but he was also an entrepreneur, lecturer, and humorist.
Two of the vices he credits with helping him write were bourbon and cigars. He was said to drink throughout his workday which led to him being referred to as the drunken father of American literature. But his smoking was no less excessive.
He’s said to have smoked up to 300 hand-rolled cigars per month. That’s 10 per day.
Whoopi Goldberg is an actress, comedian, author, and talk show host. She’s been nominated for 2 Oscars and has won 1, with a boatload of other awards under her belt to keep the shiny gold statue company.
Goldberg’s a powerhouse of dramatic acting talent and screwball comedy – the likes of which makes a rare appearance in Hollywood. She also happens to be an avid cigar smoker.
The three-time Academy Award winner first became enamored of Cuban cigars in 1973. He was filming The Last Detail and his character, he insisted, was a cigar smoker. Since filming was happening in Canada, the set was afforded easy access to Havanas.
It would be almost 20 years by the time he resumed the habit. One of his favorite smoking haunts is the Forum in LA. There he would watch most of the Lakers’ home games as he puffed away.
Rihanna is a woman of many talents, turning her hand to singing, acting, songwriting, and fashion design. She’s got a suite of awards under her belt including 8 Grammy Awards, 12 Billboard Music Awards, and 12 American Music Awards.
She’s also been known to kick back and enjoy a good cigar. She’s been spotted smoking multiple variations, from smaller Arturo Fuente Exquisito to the larger Cohiba Corona Minor. She even lit up with fellow artist Shakira in the music video for, “Can’t Remember to Forget You.”
Demi Moore is such a massive fan of cigars she appeared on the cover of Cigar Aficionado Magazine. When she’s not puffing away she’s busy ringing up a string of creative credits including actress, model, film producer, songwriter, and more.
Moore is apparently partial to small cigars like the Montecristo Joyita, but has been seen enjoying a Cohiba No. 2 or a Montecristo No. 2 on occasion.
Clint Eastwood is an enduring cultural icon. While Rawhide put him on the map, Sergio Leone’s Dollars trilogy and the Dirty Harry movies cemented his status as the quintessential badass. In the Dollars Trilogy’s case, a quintessential cigar-smoking badass.
Eastwood is credited with the idea to have his character, the mysterious Man With No Name, cut up longer cigars into stubbed cheroots to smoke. It’s a move that seared the image of a scowling Eastwood, cigar stub clenched between his teeth, into the minds of cinema-goers worldwide.
It’s also that image that lands Eastwood on just about every list of famous cigar smokers. This is in spite of never once lighting up a stogie recreationally. He apparently hated the smell of cigar smoke.
Famous Cigar Smokers Are Forever
Whether you prefer to kick back with a Montecristo Joyita or a well-named Churchill, you’re certainly in great company. Each person on this list is a master in their chosen field, bringing badassery into the world and looking mighty fine doing it.
New to the world of cigars? Here’s everything you need to know about storing cigars, so you can start your habit off on the right foot.