Famous Cigar Smokers Through History

Some faces are almost impossible to picture without a cigar. Over the last century a handful of statesmen, writers, athletes and screen icons became so linked with the leaf that the cigar itself started to feel like part of their character. This guide walks through the most widely recognized cigar smokers in popular memory and looks at what each one added to the image of the cigar as we know it today.

Statesmen and Leaders

Winston Churchill

No name is more tied to cigars than Churchill. The British wartime leader was rarely photographed without one, and the association runs so deep that a whole cigar size, the Churchill, carries his name. His silhouette, complete with cigar and defiant expression, became a symbol of resolve during the Second World War. If you want the fuller story, we cover it in Churchill and cigars.

John F. Kennedy

JFK is often mentioned in cigar circles for a widely reported story: shortly before signing the trade embargo against Cuba, he is said to have arranged for a large stash of his favorite Cuban cigars to be secured. It is repeated so often that it has become part of cigar folklore, so treat it as popular account rather than documented fact.

Che Guevara

The revolutionary figure is frequently pictured with a cigar clamped between his teeth. Whether in fatigues or in the field, the cigar became part of the rugged, defiant image that still circulates on posters and T-shirts around the world.

Writers and Thinkers

Mark Twain

The American author was famously fond of cigars and made no secret of it. He turned his habit into a steady source of one-liners, and quips about smoking are attributed to him to this day. Twain helped cast the cigar as the companion of the sharp-witted storyteller.

Sigmund Freud

The founder of psychoanalysis was a devoted cigar smoker, often shown at his desk with one in hand. His image reinforced the idea of the cigar as a thinker's indulgence, something to accompany long hours of reflection and writing.

Entertainers and Icons

Groucho Marx

For the legendary comedian, the cigar was practically a stage prop. He used it for timing, gesturing with it, pausing behind it, letting it punctuate a joke. Groucho made the cigar part of comic performance rather than just a personal habit.

Clint Eastwood

Eastwood's gunslinger roles in Sergio Leone's spaghetti westerns are among the most recognizable cigar images in film. The thin cheroot clenched in the corner of the mouth became shorthand for the silent, unflappable antihero. That is a portrayal of a character, and it left a lasting mark on how the movies use cigars.

Michael Jordan

The basketball great is well known for enjoying cigars, and images of him with one, often around golf or celebrations, are common. He helped carry the celebratory cigar into modern sports culture, where a good smoke marks a win or a milestone.

What They Have in Common

Across politics, literature, comedy and sport, the cigar tends to signal the same handful of things: confidence, patience, and a moment set aside from the rush of the day. These figures did not all smoke for the same reasons, but together they built the cultural picture most people carry in their heads. If their stories have you curious about trying one yourself, our cigar smoking for beginners guide is a friendly place to start.