15 Badasses Who Smoked Cigars

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Being a badass takes a lot of bravado, courage, and Macgyver-type intelligence. It also helps to look really cool, and smoking has been a staple of coolness and badassery since it was invented. A smart badass knows that a carefully poised cigar in hand will make him look that much more calculating and menacing (in a very sophisticated way, of course). Here are 15 total badasses who loved cigars and the quirky, lung-searing stories behind their smoky obsessions.

Winston Churchill

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Winston Churchill is remembered as one of the biggest, baddest badasses of the 20th century. During his stint as Prime Minister of England, he led his country through the most significant military event of their times, all the while promising to settle for nothing less than sweet, sweet victory. If he had had the chance, he would have punched Hitler square in his Nazi-balls. The only time good ‘ol Winston ever took a stogie out of his mouth was to zing someone with a repartee such as ‘I may be drunk, Miss, but in the morning I will be sober and you will still be ugly.’ Churchill smoked so many cigars (according to some, eight to ten a day) that they (cigar congress?) eventually named a cigar size after him. No surprise – it’s on the higher end of the scale.

Groucho Marx

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Groucho Marx was perhaps the most amazing comic mind the United States ever produced. His over-the-top signature look of thick glasses, a fake grease-paint moustache, and of course the trademark cigar, is forever etched into the collective consciousness and can be seen on novelty shop counters to this day. A famous story goes that Groucho’s wife, who hated his cigar-smoking habit, was once so disgusted by his ‘stinky old cigar’ that she ordered him to extinguish it or go and find a new wife. Considering that Groucho had three different wives over the course of his life, and divorced each and every one of them, we’re pretty sure we know how that one ended up.

Orson Welles

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The famous Orson Welles was somewhat of a wunderkind. At only 25 years of age he directed and starred in Citizen Kane, considered by many cinema snobs to be the finest American film ever made. Besides Kane, he directed a slew of other films that are now considered American classics, including The Magnificent Ambersons, Touch of Evil, and F For Fake. Apparently, Welles intentionally wrote cigar-smoking characters into his films, so much did he love lighting up a stogie himself. Welles was a famous lover of the good life: champagne, cigars and beautiful women. Besides his amazing filmmaking skills, he is renowned as the man who was able to hold on to Rita Hayworth for the longest period of time of any man, from 1943 to 1948. When she filed for divorce from Orson, the reason she cited was ‘I can’t take his genius any more.’ Even when he’s getting divorced the guy is getting lauded. Now that’s a badass.

Sigmund Freud

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Sigmud Freud wasn’t messing around when it came to cigar smoking. He reportedly puffed through an average of 20 cigars a day without batting an eyelid, even though his friends constantly warned him of the negative effects of lighting up. After he was diagnosed with mouth cancer and had a lump growing in his mouth, he totally gave up smoking cigars! Just kidding, he just kept smoking anyway, ignoring the serious illness that was besetting him. Freud (who was famed for his theories regarding phallic symbolism),
when challenged by his colleagues for constantly smoking cigars (which they considered a strong phallic symbol) uttered his now-famous quote: ‘sometimes a cigar is just a cigar.’ You just know that if it had been one of his contemporaries who was stogie-addicted, he would have said, ‘sometimes a cigar is just a huge c@%k that you like putting in your mouth all the time.’

Fidel Castro


Fidel Castro more or less stands as the poster child (using the word ‘child’ loosely) for the glory that is the Cuban cigar, a stogie revered by many as the absolute crème de la crème. Castro gave up smoking cigars in 1985 facing serious health concerns that could jeopardize his place in office. This marked the end of 40 years of puffing away like some sort of crazed locomotive, and so ingrained were cigars in the dictator’s mind that he would regularly find himself dreaming about smoking a cigar and consequently admonish himself for the fact. Castro’s profound love for his homeland’s most famous produce was certainly no secret to the US, who once tried to assassinate Castro using an exploding cigar. Unfortunately for the CIA, they purchased the booby-trapped cigar from Acme Corp, and it failed to go off until they were scrutinizing its failure during a board meeting.

John F. Kennedy

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When he wasn’t out being a badass by scoring with the likes of Marilyn Monroe, JFK loved to kick back with a nice cigar and just contemplate how awesome he was. A famous story about Kennedy goes that the night before he was to sign the papers for the imminent trade embargo with Cuba, he sent his press secretary, Pierre Salinger, off to buy up as many H. Upmann Petit Upmann. Cigars as he possibly could, and consequently that Kennedy specifically held off signing the papers until he could feel the sweet, tender rolled leaves clenched in his cigar-mad hand. In the end, Salinger was able to round up 1200 Petit Upmanns for the president and, considering that he was tragically assassinated a short couple years after the embargo was put into place, it’s safe to assume that the Bostonian Prince has more than enough tightly-rolled goodness to make him a very satisfied badass.

Babe Ruth

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The Babe, the Sultan of Swat, the King of Crash, the Colosus of Clout, The Great Bambino. All of these names belonged to one amazing baseball player: George Herman Ruth, Jr., better known as Babe Ruth. The Babe was a pitcher for the Red Sox before being traded to the Yankees in 1919. When he was still living in Boston, Ruth invested in a cigar factory that produced nickel smokes, and quickly had one of the factory’s products named after him, the ‘Babe Ruth Perfecto.’ A legendary story goes that Ruth once brought a woman home while sharing a room with Ernie Shore, who for some reason or another found it very difficult to sleep that night. When Shore found five cigars stubs strewn around the area where the Babe was sleeping, he asked his friend why he had smoke so many cigars in a night. “Oh, that!” Chuckled Ruth. “I like a cigar every time I’m finished.”

Che Guevara

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It would be extremely remiss to compile this list and include Castro while neglecting to include his famous contemporary, Ernesto “Che” Guevara. While most people today know Che as ‘that guy on all the t-shirts,’ he was once an extremely notable Marxist revolutionary who gained a steady and loyal following in the 1950s and 60s. Like his communistic brother, Fidel Castro, Che loved nothing more than to light up a stogie and contemplate his own ineffable badassery. Adding to this is the fact that Che was an asthmatic, and chose to adopt the Cuban practice of burning madly through cigars anyway, constantly undergoing the risk having an attack. “Lungs? Who needs them? I’m a god damn revolutionary!”

Al Capone

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It doesn’t get much more badass than Al Capone. He started out his lucrative and lurid criminal career in his native New York and eventually moved across to Chicago to run the notorious ‘syndicate.’ He stands today as probably the most famous gangster that ever lived, and despite his infamy as a crook and the gangland murders in which he was embroiled, he remains a steadfastly romantic figure in American history. When Capone was eventually sent to jail, it was for a far less badass crime than one would expect: tax evasion. Capone, possibly in a state of embarrassment of the wussiness of his criminal conviction, kissed goodbye his freedom not by drinking the liquor he was so famous for bootlegging, but rather by lighting up a nice fat cigar and puffing all the way to Alcatraz.

Peter Falk


Any one who doesn’t know who Peter Falk is should immediately go online (or to a video store if you are a caveperson) and rent the series Columbo, because a bigger exercise in badassery there never has been. Do it. Now. We’ll wait.
The wry, unassuming detective in his trench coat, his hair slightly dishevelled, and always, always, with a cigar firmly clenched in his hand. Falk’s Columbo was the master of tricking murderers into giving themselves away by appearing to be nothing more than an over-the-hill, fumbling, fuddy duddy detective who wouldn’t know a murderer from a synchronized swimmer. Really, all those stupid perps needed to do was look down and see that stogie and they would know. Never mess with Columbo.

Clint Eastwood

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Clint Eastwood  is undoubtedly one of the most important symbols of masculinity in the cinema. His roles in Rawhide, Sergio Leone’s Dollars Trilogy, and the Dirty Harry movies cemented his badass status in the minds of audiences all over the world. Interestingly, Eastwood is the only person on this list who actually hated the smell of cigar smoke and never lit up a stogie recreationally, but that didn’t stop him from doing it better than 100 cigar aficionados combined. Eastwood’s famous cigar smoking (and the badassery that emanated there from) occurred in the aforementioned Dollars Trilogy, in which Eastwood played the mysterious Man With No Name. It was originally Eastwood’s idea to cut up longer cigars into little stubbed cheroots for his character to smoke, a trademark that is burned into the minds of moviegoers the world over. Only Eastwood could get away with detesting cigars and still smoking them like an utter badass.

Alfred Hitchcock

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We move now from the master of cool to the master of suspense, Alfred Hitchcock. Hitchcock is famed for directing some of the greatest American films of all time, including Psycho, The Birds, North By Northwest, and Vertigo. Besides being a gifted and revolutionary director, Hitchcock knew better than any of his contemporaries how to market himself. He was one of the first directors who made himself visible to the public, both through appearing in promos for his films, speaking directly to the audience, and through making small cameos in his films. Not only did he have a very distinctive voice, but he also had a physical presence and demenor that left an indelible impression. Part of this impression was formed by his wardrobe, which wouldn’t be complete without his trademark bowler hat and accompanying cigar, which he puffed on excessively, creating clouds of smoke into which he hoped to lead his unsuspecting audience.

General George S. Patton

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General Patton was an incredible badass. Besides being one of the most revered Generals in modern warfare, he just didn’t take crap from anyone. He was harangued in the media several times for kicking his men in the pants when they failed to live up to his badass expectations, and for ordering his men to shoot a mule that stood blocking a bridge he wanted to cross. Patton was such a cigar fiend that he didn’t just carry a nice big box of Cuban with him, but rather forced his men to carry around his own personal humidor full of Havana’s finest whenever they were out on assignment. You can just picture him now, ordering his troops to decapitate a water buffalo that ‘looked at him kinda funny,’ all the while drawing away on his Cuban before riding off into the sunset.

Mark Twain

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It’s almost as if Mark Twain looked into the future, saw the people on this list, said, ‘pffft – pussies,’ and proceeded to smoke anywhere between 22 and 40 frickin’ cigars a day. Based on sheer volume of smoke inhaled, good ‘ol Samuel Clemens, aka Mark Twain, has got the field well and truly dominated. He might also be vying with Groucho Marx for the ‘funniest cigar smoker’ award. After his death Twain waslauded as the greatest American humorist of his age in his obituary in the New York Times, and The Adventures of Huckleberry Fin has been widely called the Great American Novel. Despite his keen sense of humor, Twain was damn serious about cigars, once asserting ‘if smoking is not allowed in heaven, I shall not go.’ Twain went on to write essays specifically on cigars and how they can transform any ordinary man into a badass and any great man into a legend.
 

Thomas Edison

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The Wizard of Menlo Park might better have been known as the Badass of Menlo Park. Edison was not only a revolutionary inventor, he was a cigar aficionado who always coupled his creative and electrical sparks with sparking up a stogie and basking in its warm red glow. Edison is also renowned for being a bit of an a-hole to his contemporaries, including Nikola Tesla whose alternating current he tried to decry as dangerous by publicly electrocuting animals as a demonstration of its ‘instability.’ He was also known to plant cigars rolled entirely from sawdust in his drawer in order to punk unsuspecting lab assistants who regularly pilfered his precious stogies. Edison may have been a bit of a jerk, but he certainly knew the recipe for success: a liberal splash of creativity, a sprinkle of douchebaggery, and one stick of tobacco.

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John Pullo

John Pullo

Managing Editor at CigarAdvisor.com

This is not his picture, nor does John even have a beard. Interestingly, his Social Security number is all ones. All we can say is " "You will know him by the mullet he wears." "

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