Cigar Lifestyle

Top 5: My Favorite Famous Cigar Smokers of All Time

Reading Time: 7 minutes

My 5 Favorite Famous Cigar Smokers of ALL Time

By Tommy Zman

Just surf online and you’ll find countless lists of world famous cigar smokers – but I didn’t want to just crank out another list…I wanted this list to mean something to me, and hopefully to you as well. So, I broke my list into five categories: Politics, Sports, Entertainment, Writing and Business, and picked men who not only vehemently loved their premium hand rolled sticks, but were also bad-asses in their own way, guys who played by their own rules and made a difference in their chosen fields. So here’s what I think would be one hell of an awesome gathering of guys who would be amazing to herf and hang with. They’d talk endlessly about their life adventures and grace us with their famous quotes, all while firing up the cigars they loved.


famous cigar smokers churchillPoliticians have long been known for puffing their fat, expensive cigars while making world changing deals in smoky back rooms. But there is without question, no greater political figure who professed his voracious love for the lavish leaf than the Prime Minister of the United Kingdom, Sir Winston Churchill. Old Winnie was indeed a bad-ass to the max, taking on Adolf Hitler’s Germany while assuring the people of Great Britain that they would be victorious. He truly did not give a damn what others thought of him, especially when it came to his insane love for cigars as he smoked them all day long and everywhere he went. The stubborn s.o.b. even smoked in bed, ruining many a pair of silk pajamas, forcing his wife to make him a nighttime cigar bib. It is estimated that Sir Winnie smoked – yeah, you’re about to read this correctly, over 250,000 premium Cubanos during his lifetime – that’s a quarter of a million cigars. While I don’t have a calculator handy, that translates to one hell of a shit-load per day. When the Romeo y Julieta factory in Havana named the Churchill size after the Prime Minister, I think that pretty much solidified him as the world’s all-time greatest cigar smoker.

My Favorite Churchill Quotes:

“I drink a great deal. I sleep a little, and I smoke cigar after cigar. That is why I am in two-hundred-percent form.”

“I may be drunk, Miss, but in the morning I will be sober and you will still be ugly.”



famous cigar smokers miguel angel JiminezWhen you talk about famous cigar smokers in the sports world, you immediately think of the immortals like Michael Jordan, Wayne Gretzky and Babe Ruth; but it’s the Spanish-born professional tour golfer, Miguel Angel Jimenez who tops my list. The man is a cult hero on the European tour with over thirty victories to his name and he is the epitome of bad-ass in every way. Much like we said of Churchill, Jimenez cares not what others say about his openly brash ways, while playing a game that is known for etiquette and gentlemanly sportsmanship. He struts the fairways with his long, flowing blond curly locks of hair while puffing a large premium cigar the entire round. And with his many victories, comes the big prize money, money spent on lavish, and decadent good-life rewards like fine wines, rare whiskies, exotic rums, and of course one hell of a collection of expensive premium hand rolled tobacco treats. He often hears flack from fans and competing golfers alike who profess their disdain for his public puffery, but as you might only guess, he laughs in their faces while sinking another winning putt. The title of the April 2015 article sums it up best: Miguel Angel Jimenez Really, Really Does Not Care What You Think.

My Favorite Jimenez Quote:

“I come from a different generation. And I’m not a hypocrite. I don’t hide the way I am. If I want to have a drink, I have a drink. Why shouldn’t I? Is it illegal to drink alcohol? Is tobacco illegal? So why should I care if people see me smoking? I do what I do out in the open. If people have a problem with that they can stick their tongue up their ass and let the rest of us do what we want to do.”



famous cigar smokers Jack NicholsonSure, there are a myriad of actors, singers, comedians and what have you who are known for their cigar infatuation, but when it comes to flat out bad-assery personified, I’ve gotta roll with Jack Nicholson. Every character Jack has ever played in the scads of movies he’s performed in has a ballsy edge, much like the man in real life – a rebellious Tinsel Town legend who has always blurted out what’s on his mind. And yeah, Nicholson just loves his cigars, a lifestyle that began some years back when he wanted to give up his addiction to cigarettes. He openly says he’s not a full-out cigar expert, but he knows what he likes, and he loves Montecristo, Cohiba and Romeo y Julieta. And as far as what’s on his mind, he has referred to the anti-smoking movement as a “waste of time”. Jack holds the honor of being the most nominated male Academy Awards actor of all time. His most prominent roles are masterful and unforgettable in cinematic greats such as Chinatown, One Flew Over the Cuckoo’s Nest, The Shining, Prizzi’s Honor, Reds, the Joker in the 1989 Batman film, and of course, the acerbic prick of a Marine Corp Colonel named Nathan R. Jessup. Nicholson is one of those brash, larger than life people who plays by his own rules and if you don’t like it, he’ll quickly remind you that “you can’t handle the truth!”

My Favorite Nicholson Quotes:

“The only way to break a bad habit was to replace it with a better habit.” Nicholson, explaining why he switched from cigarettes to cigars.

“With my sun glasses on, I’m Jack Nicholson. Without them, I’m fat and 60.”


famous cigar smokers mark TwainWhen you talk about guys who lived on their own terms, Samuel Langhorne Clemens is pretty damned high on the list. He’s the writer of over 30 books, newspaper man, entrepreneur, publisher, and a humorist and lecturer who entertained the hell out of audiences in the 1800’s with his own special brand of the spoken word. He was a surly dude who always spoke his mind, especially of his massive disdain for politicians, often attacking them in his articles and during speaking engagements. He had a tremendous fascination with technology and spent a lot of time with his close friend, Nikola Tesla in his laboratory. Two of Twain’s absolute loves in life were bourbon and cigars, both of which he consumed in excess. He’s been referred to as the drunken father of American Literature, known for consuming his hooch the entire work day long. As for his affinity for hand rolled cigars, he says in his writings that smoking helped free his creative mind as he would consume up to 300 sticks per month. That’s ten per day, 3,600 per year, yeah keep doing the math. Anybody got a case of Altoids? Of course, he’s best known for the literary classics, The Adventures of Tom Sawyer and the Adventures of Huckleberry Finn along with a litany of fiction and satirical work. And he just might be one of the most quoted writers ever; just Google his name and you’ll be reading for a while.

My Favorite Twain Quotes:

“Politicians and diapers must be changed often and for the same reason.”

“I never smoke to excess – that is, I smoke in moderation, only one cigar at a time.”


famous cigar smokers milton HersheyAt around the turn of the century in 1900, Milton Hershey was a confectioner and a millionaire creating his much sought after caramels. But it was a trip to Europe that showed him the deliciously sweet world of chocolate and the machinery that made the treats. Chocolate was considered a luxury in the U.S. and it was his vision to make it affordable to all. He sold his confections business, purchased a mammoth amount of farm land in Lancaster County, PA, and started the Hershey Chocolate company, beginning with the Hershey Bar and then his world-famous Kisses. Milton was a fanatical cigar lover, smoking between 8 and 10 per day while always seen with a cigar in his mouth as his friends said his huge home always had the aroma of a fine stogie. But it wasn’t until his trips to Cuba (purchasing the sugar cane for his chocolate) that he truly developed his passion of hand rolled happiness, his favorite being Cuban Corona-Coronas. While the man was an absolute titan of industry, he was also one of the most benevolent philanthropists there may have ever been. He needed workers for his huge factory, so he built their houses, the schools, the hospital, the roads and all the infrastructure to create his chocolate town. He loved children and made sure they had the best educations possible. Hershey was one hell of a sweet guy and another legend who did things his way.

My Favorite Hershey Quotes:

One is only happy in proportion as he makes others feel happy.

“When I started making chocolate I didn’t follow the policies of those already in the business. If I had, I would never have made a go of it. Instead, I started out with the determination to make a better nickel chocolate bar than any of my competitors made, and I did so.”


So, there’s my list – 5 famous cigar smokers, bad-asses one and all, who rock their field of play and always made a difference. Let me know your thoughts in the comments below along with some of your favorite lovers of the leaf.

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Jose Hernandez
5 years ago

Good picks !

Jack Bliesath
5 years ago

Excellent picks. I don’t know about the sports pick but the rest are plenty notable. I could never smoke that many cigars!!

Hamlet Hernandez
5 years ago

Great picks. This is my list. Politics: Churchill(the man has a cigar size named after him). Sports: Michael Jordan. Entertainment: Arnold Shwartzenegger(he could be on all the first three categories). Literature: Ernest Hemingway. Business: J P Morgan

Joe Montelle
5 years ago

Nice picks Tommy. I think they all had/have a little Zman in them!

Joe Cappa
5 years ago

Great pics. i’m a cigar smoking barber in Pa. Possibly in the top 5 in my section of the state! Nothing better than a good stick. I change brands frequently, into Gurkha samplers now.

Michael Flores
5 years ago

JFK was also a “big brother” of the leaf.

Phil Hilliard
5 years ago

Mr. Hershey tops the list. Hershey Bars and Hershey Kissses are the ultimate American invention. Thank you Mr. Hershey. You deserve as many cigars as you want. (One or two per day usually suits me, though.)

Richard DeFay
5 years ago

Great article! Excellent choices. Well written, my friend.

Ronny Avo Jr Uvezian
5 years ago


Dennis Saum
5 years ago

I never knew Hersey was a cigar smoker.. Good list.

Steven Pardoe
5 years ago

Awesome read Tommy!

Steve Richards
5 years ago

George Burns..he’s even got the name dialed in!

Victor Esposito
5 years ago

they loved cigars and so do I

Laszlo Keszthelyi
5 years ago

Nice write up Tommy Zarzecki!

Victor Esposito
5 years ago

there’s nothing like a great cigar after a big meal and a bourbon that’s where it is paradise

Jeff Wurst
5 years ago

You forgot me you Polish baastad.

John OConnell
5 years ago

Nice work Zman, like Jiminez, 2d choice would’ve been Red Auerbach, but then I’m Old School.

Jonny Blaze
5 years ago

Most of the ones that came to my mind (besides those Tommy listed) were in Entertainment.
Groucho Marx
Arnold Schwarzenegger
Sylvester Stallone
George Burns

The only Sports figure I could think of was Babe Ruth! LOL

George Jannino
5 years ago

Gotta include Red Auerbach

Mark Fischer
5 years ago

All these people are famous cigar smokers !!! But I believe all of us! …The common man, Are the most famous!!!

Cliff Kammerdiener
5 years ago

Love the list ZMan!! It was good… I would have included George Burns, Groucho, Arnold… but then ones you named have to be in the group too…

Travis Stirewalt
5 years ago

Great job there Zman!

Craig Richards
5 years ago

I’ve always admired Milton Hershey, being from near the Hershey area, but I like him even more now.

Rich Hubbs
5 years ago

That’s one hell of a list. I never knew Milton Hershey was a cigar smoker. He’s near the top of my favorite successful Americans.

Aveek Ray Mukherjee
4 years ago

Was Twain fond of cigars or pipe?

Tommy Zman Zarzecki

Tommy Zman Zarzecki


Tommy Zman, is an obsessive enjoyer of life’s leafy pleasures. Growing up in the bowels of northern New Jersey, parented by an eccentric Polish father and a neurotic Italian mother, what else could this man possibly be other than a humorist? ZMan’s a real throwback to a time when men were kings of the castle and smoking a cigar in public didn’t label you an outcast and a pariah. He’s an old–school down to earth guy - but when it comes to p.c. tyranny and nanny-state legislature, he’ll draw his sword and swing for the fences. Tommy gathered a faithful following as a longtime feature writer at Cigar Magazine, and his testosterone laden FaceBook community, CROMAG NATION™ is truly the last great bastion for Men’s Men.

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