Famous Cigar Smokers in History

One of the most recognizable faces of the 20th century got that way because a photographer stole his cigar. On December 30, 1941, Yousuf Karsh photographed Winston Churchill in Ottawa, plucked the stogie out of his mouth, and captured the scowl that became "The Roaring Lion" — a portrait TIME later named among the 100 most influential photographs ever made.

That's the thing about famous cigar smokers. The cigar isn't a prop. It's part of the story — the pause before the punchline, the thing in the hand that says I've got time. Before you meet the icons, it helps to know how a cigar is actually meant to be smoked.

Was Winston Churchill the most famous cigar smoker ever?

He's the benchmark. Karsh's 1941 portrait — one of the 100 most influential photographs of all time, per TIME — worked precisely because the cigar was missing. Churchill's habit was so tightly bound to his image that removing it for two seconds produced the most famous scowl in modern photography.

The devotion ran deep. Churchill visited the Romeo y Julieta factory in Havana in 1946, and the brand named a 7 x 47 parejo after him. That name outlived the man. Walk into any humidor today and you'll find a Churchill from a dozen different brands, most of them with no connection to Havana at all.

Want proof the man's leftovers were treated like relics? In 1953, an usherette at the London Coliseum named Violet King picked a half-smoked cigar off the floor after Churchill dropped it. She kept it. Decades later it went to auction with an estimate around $6,000 to $7,000. For a butt.

Churchill also understood the ritual, which is more than most people can say. If you've ever scorched a wrapper with a gas station lighter, our guide on lighting a cigar the right way will save you some embarrassment.

How many cigars did Mark Twain actually smoke?

By his own accounting, as many as 22 a day — and he claimed his first at age eight. Twain wasn't shy about it either. He wrote about tobacco constantly in the letters and autobiography that still fill shelves in the American literature canon NPR's books desk covers, and he treated quitting as a running joke.

The line everyone quotes: "Giving up smoking is the easiest thing in the world. I know because I've done it thousands of times." He also described trying to limit himself to one cigar a day, then buying progressively larger cigars until the single daily smoke was the size of a walking stick.

Twain was writing for The Atlantic Monthly in the 1870s, at the height of his fame and his habit. Cheap cigars, mostly. He was famously unbothered by quality — a stance that would get him roasted in any modern lounge.

Here's what he did get right: the cigar as a thinking tool. Twain smoked while he wrote, and he held one the way a man holds a pen. If you'd like to look like you know what you're doing, we broke down how to hold a cigar without looking like a rookie.

Did cigars really make Ulysses S. Grant famous?

They made his image. After the Battle of Fort Donelson in February 1862, newspapers described Grant smoking through the fight. Admirers responded by mailing him more than 10,000 boxes of cigars. A light habit turned heavy fast — by most accounts around 20 a day — and he died of throat cancer in 1885.

That's the part of the legend people skip. Grant's cigar was a press invention that became a real addiction, and it almost certainly killed him. He finished his memoirs while dying, racing to leave his family something to live on.

Is it possible to admire the image and still be honest about the ending? We think so. Cigars are an occasional pleasure, not a daily requirement, and the men on this list mostly learned that too late.

Grant also gave us the earliest version of something you'll still see in any lounge: the cigar as a social handshake. Cigar culture rewards the guy who shows up, sits down, and shuts up for a minute. New to that room? Read what to expect your first time at a cigar lounge.

Why is Fidel Castro tied to the Cohiba?

Because the cigar was literally made for him. Cohiba began in 1966 as Castro's private blend at the El Laguito factory in Havana, rolled by Eduardo Rivera. It wasn't sold. It was given — Cuba's official diplomatic gift to visiting heads of state, and a fixture in the island's political history.

Castro started smoking at 15. He quit in 1985, at 59, to put his weight behind Cuba's national anti-smoking campaign — a turn covered widely across Latin America news desks at the time. The most famous cigar smoker alive gave them up for public health. Say what you want about the man; that's a plot twist.

Cohiba went from state secret to the most imitated name in cigars. Ask anyone who's been handed a suspiciously cheap box in Havana — the counterfeits are their own kind of tribute.

The mystique never faded either. That's exactly why the Cuban aesthetic still moves — we wrote about it in our roundup of Cuban cigar shirts and the style behind them, and it's the same energy behind the Cuban Cigar softstyle tee.

What do iconic cigar smokers have in common today?

A signature. Churchill had the size named after him, Twain had the joke, Grant had the boxes, Castro had the blend. In 2025, the Cigar Association of America reported 429.8 million premium handmade cigars imported into the United States — flat against 2024, and the fifth consecutive year at or above 400 million. The ritual isn't going anywhere.

The country mix tells its own story. Nicaragua shipped 258.4 million premium cigars in 2025, up 2 percent. The Dominican Republic sent 93.7 million, down 12 percent. Honduras moved 74.5 million, up 11 percent. Cuba's shadow still looms over the culture even though it's absent from the American numbers entirely.

So what's your signature? Most guys don't get a cigar size named after them. What they get is a shirt — the one they wear to the lounge, to the backyard, to the poker table where everyone already knows what they're drinking. Our Vintage Cigar Lion tee is built on that idea: retro linework, a little swagger, zero explanation required.

Frequently Asked Questions

Who is the most famous cigar smoker in history?

Winston Churchill, by a wide margin. Romeo y Julieta named a 7 x 47 size after him following his 1946 visit to their Havana factory, and nearly every brand still sells a "Churchill" today. Yousuf Karsh's 1941 portrait of him remains one of TIME's 100 most influential photographs.

How many cigars did Mark Twain smoke a day?

Twain claimed as many as 22 a day, and said he smoked his first at age eight. He was open about failing to quit, joking that giving up smoking was easy because he'd done it thousands of times. His autobiography and letters are the primary source for those numbers.

Why is a cigar size called a Churchill?

Because Winston Churchill favored that shape. After he visited the Romeo y Julieta factory in Havana in 1946, the brand named its 7 x 47 parejo after him. The name spread across the industry, and today most cigar makers offer a Churchill regardless of any Cuban connection.

What cigar did Fidel Castro smoke?

Cohiba, created in 1966 as his private blend at Havana's El Laguito factory and rolled by Eduardo Rivera. It became Cuba's official diplomatic gift to foreign leaders. Castro began smoking at 15 and quit in 1985, at 59, to support Cuba's national anti-smoking campaign.

Are premium cigars still popular in the U.S.?

Yes. The Cigar Association of America reported 429.8 million premium handmade cigars imported into the United States in 2025 — essentially flat versus 2024 and the fifth straight year at or above 400 million units. Nicaragua led with 258.4 million, followed by the Dominican Republic and Honduras.

The bottom line

Churchill, Twain, Grant, Castro — none of them were trying to build a brand. They just did the same thing often enough that it became shorthand for who they were. That's what a signature is. Pick yours, and wear it: browse the cigar tee collection.