Cigar Lifestyle

15 Badasses Who Smoked Cigars

Reading Time: 8 minutes

Here are 15 total badasses who loved cigars and the quirky, lung-searing stories behind their smoky obsessions.

Winston Churchill

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 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

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

The famous 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

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.’

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.

John F. Kennedy

When he wasn’t out being a badass by scoring with the likes of Marilyn Monroe, 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

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 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

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.

Al Capone

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 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

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

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

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 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 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

It’s almost as if Mark Twain looked into the future, saw the people on this list, said, ‘pffft – pussies,’ and proceeded to 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 was as the greatest American humorist of his age in his obituary in the New York Times, and The Adventures of Huckleberry Finn 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

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 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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11 years ago

Enjoyed this very much. All those represented are to be admired for their dedication to cigars if not for their character or behavior in other areas. I have one small complaint; The image depicting Groucho Marx is not the legendary comedian and devotee of Dunhills but rather Frank Ferrente a Groucho impersonator. Groucho is among the greatest talents (and cigar smokers) this country has produced and deserves to have his actual photo included.

11 years ago

Enjoyed this very much. All those represented are to be admired for their dedication to cigars if not for their character or behavior in other areas. I have one small complaint; The image depicting Groucho Marx is not the legendary comedian and devotee of Dunhills but rather Frank Ferrente a Groucho impersonator. Groucho is among the greatest talents (and cigar smokers) this country has produced and deserves to have his actual photo included.

Suna Germen
6 years ago

Mustafa Kemâl Atatürk de yalnızca Türk tütünü sigaraları içti..
Mustafa Kemal Ataturk smoked Turkish cigarettes,which (was,once upon a time,till America messed it up like all the other rest) ..

David Pearce
6 years ago

Where’s Arnold??? I thought he’d make it over Clint since he actually likes cigars.

Elise Tissot
5 years ago

Where’s George Sand??

Rusty Tubbs
5 years ago

Castro, Che and Capone…..really??? They were all murderers.

Juan Serda Jr. Serda
2 years ago
Reply to  Rusty Tubbs

Fool! We are all murders. Read your history, dumbass!

Rocky Rockwell
5 years ago

US Grant and his sidekick William t. Sherman – Where would all you’re listed “badasses” be without their stategic brilliance! Check out the Vicksburg Campaign!

Marilyn White
5 years ago

JFK? A BADASS? What did that mobsters spoiled brat do , aside from being assassinated in Dalas, that made him anything but a wuss?
As to funny men, I didn’t see George Burns listed. I can’t say he was as intellectual as Clemens (Twain), But he was surely as funny as Groucho.

Juan Serda Jr. Serda
2 years ago
Reply to  Marilyn White

Your knowledge of history is as stupid as your spelling, Dumbass! It’s Dallas, Texas pendejo!
JFK served his country with honor when he could have had a desk job. He joined a brotherhood instead of being a draft dodger or fleeing to Canada like Trump.

1 year ago

PRESIDENT Trump to you Comrade Commie!
And he DIDN’T flee to Canada dumbass STOP WATCHING FAKE NEWS!
Trump 2024!
If not sooner, the illigitimate Idiot in Charge YOU voted for has been a DISASTER for our Republic and has the Blood of Thousands and Rapes of little Girls on his hands (but that probably just makes the pedio OBiden hard) OBiden is OWNED by Russia and China who are Blackmailing him with His drugged out Son Hunters lost Laptops!
Yes dumbass that is PLURAL Russian Drug dealers stole one of his laptops in an 18 day Crack and booze binge, and of course the infamous left behind Laptop in a Repair Shop! And it is WIDELY known China agents may have HACKED IT, and why not they just HACKED THE DEPT OF Defense.
Senile Jim Crow Joe must have left DOD off of his list of 16 places not to Hack He gave to Vladimir!
Not like the FAKE Russian Investigation of a FAKE Dossier Hillary PAID FOR to have made! Or that those that entered OUR Capital there was an NO EVIDENCE OF it being an ORGINIZED planed event! The FBI also declared it was a SPONTANEOUS event and NO ONE INCITED IT! That is all a FACT!
So his Impeachments are ALSO based on FALSE evidence in other words DemComs LIED!
SO GFY Comrade these are all FACTS!

Last edited 1 year ago by Randall
Tony Amarillas
5 years ago

They forgot Winston Churchill and Michael Jordan!

David B Fowler
5 years ago

Arnold, Strahan…

Carolyn Tronolone
5 years ago

tae loved his cigars and id love to hear some of the stories about him and his cigars and pranks

Aveek Ray Mukherjee
4 years ago

Dolph Lundgren?

Chris Kapernick
4 years ago

Isambard Kingdom Brunel, this man smoked more then 40 large cigars a day and lived on four hours of sleep a day. He was a great engineer too.

Kevin Miller
4 years ago

Of course included in famous cigar smokers was General Grant from the civil war but also “The TORCH of Atlanta and Columbia”….General William Tecumseh Sherman who always had a cigar…smoking and chewing on the end.
..some say the general who actually shortened and WON the civil war for the Union…and I contend, a bigger, smarter BADASS than Grant.

Mike Tomlin
2 years ago

George Burns

Will Sergent
2 years ago

Apparently somebody is so badass that they cant find an editor or proofreader to work with them.

Dirk Hammersmith
7 months ago

You lost me at “lung searing.”

John Pullo

John Pullo

Editor in Chief

This is not his picture, nor does he even have a beard. A solid 'B' student and occasional low-fi musician, John is a medley of cynicism and sarcasm crammed into a wrinkled Oxford shirt who makes it nearly intolerable to watch reality television with him in the same room. Interestingly, his Social Security number is all ones.

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