The smoking ritual has followed public life for a very long time. Long enough that some of the most iconic images in twentieth and twenty-first century culture involve a lit cigar in the frame. A boxer at a post-fight press conference. A basketball star in the locker room after a championship. A president leaning forward in the Oval Office. A movie character walking into a saloon with a cigarillo between his teeth. These are not accidents. They are the visual language of a culture that used the smoke to mark the moment.

The famous smokers below span every major smoking format — full cigars, cigarettes, and cigarillos. Each carries a slightly different tradition, and each shows up in public life in a slightly different way. The point of walking through them is not to endorse the choice. It is to look honestly at how the ritual has survived, adapted, and continued to earn its place across generations of athletes, actors, musicians, and public figures.

Athletes and the Championship Cigar

Nowhere is the smoking ritual more publicly on display than in professional sports. The championship cigar is now a category of image on its own, and the athletes who have made the frame iconic have done more to shape the modern cigar’s public presence than any advertising ever did.

Michael Jordan

Few athletes are more publicly associated with cigar smoking than Michael Jordan. Locker room celebrations, private post-game rituals, and countless golf outings have made the cigar a fixture of his public image. Jordan’s cigar collection has been the subject of long-running press coverage in the cigar industry, and his post-retirement Charlotte Bobcats era only deepened the association. The championship cigar tradition owes a real debt to how Jordan carried it during the Chicago Bulls dynasty years.

Shaquille O’Neal, Charles Barkley, and the NBA Cigar Culture

Shaquille O’Neal has been photographed with a cigar in his hand for decades. Charles Barkley has spoken openly about his cigar habits on television. The NBA has produced more visible cigar smokers than any other American professional sport, and the tradition has continued into the current era. Post-championship images of LeBron James and other stars enjoying a cigar in the locker room are now expected rather than surprising.

David Ortiz and the Baseball Tradition

David Ortiz turned the World Series championship cigar into something close to a personal signature. His public appreciation for the ritual — extending well into his post-playing career — helped keep the baseball cigar tradition alive in a modern era that often pushes back against smoking imagery of any kind. Ortiz sits in a lineage that stretches back to the mid-twentieth century, when baseball clubhouses were regularly filled with cigar smoke after big wins.

Wayne Gretzky and the Hockey Cigar

Wayne Gretzky is a documented cigar enthusiast whose association with the format goes back decades. Stanley Cup celebrations across the NHL have long included cigars in the visual grammar of the moment, and Gretzky’s public affection for the ritual is one of the reasons hockey retained its own version of the tradition through the era when the imagery began to fade elsewhere.

Tiger Woods and the Ryder Cup Frame

Golf and cigars go together in a way few sports match, and Tiger Woods has been photographed with a cigar during more than one major moment. The Ryder Cup, the Masters practice rounds, and casual weekend rounds have all produced images of Woods enjoying a cigar between shots. The golf-and-cigar pairing rewards the athlete who wants to slow down between shots, and the format has a natural home on the course.

Arnold Schwarzenegger — Athlete Turned Cultural Icon

Arnold Schwarzenegger’s cigar collection is legendary. As a bodybuilder, actor, and former governor of California, Schwarzenegger has been photographed with a cigar in every stage of his public career. His cigar habits have been the subject of documentary attention and industry coverage. Few public figures across any category have kept the cigar ritual as visible as Schwarzenegger has over the last five decades.

The Cigarillo on the Silver Screen

The cigarillo has a very specific place in film history, and much of that place was built by a small handful of iconic performances. The format’s short length, natural leaf wrapper, and quick lighting made it visually distinct from the larger cigar and more compelling on camera than a cigarette.

Clint Eastwood

Clint Eastwood’s small cigarillos in the Sergio Leone spaghetti Western trilogy — A Fistful of Dollars, For a Few Dollars More, and The Good, the Bad and the Ugly — created one of the most enduring cigarillo images in film. The cheroot-style cigarillos he chewed between his teeth became inseparable from The Man With No Name character. Eastwood has since spoken publicly about not being a regular smoker in real life, but the on-screen association has done more for cigarillo imagery than nearly any other single performance.

Charles Bronson

Charles Bronson’s tough-guy screen persona in films like Once Upon a Time in the West and the Death Wish series often featured a cigarillo as part of the visual package. Bronson’s cigarillo scenes belong in the same visual tradition Eastwood helped establish — a lean, no-nonsense format for a lean, no-nonsense character.

Anthony Hopkins and Character-Study Cigarillos

Anthony Hopkins has featured cigarillos in multiple roles across his long career. The format tends to appear when a character is meant to convey control, contemplation, or a certain worldly weariness — three modes Hopkins has occupied on screen more than most.

Presidents and the Cigar Tradition

Winston Churchill

Winston Churchill’s cigar is not a footnote. It is a defining part of his public image. Churchill smoked large-format cigars publicly for most of his adult life, and the imagery has become so recognizable that a specific cigar size — the Churchill — is named after his preference for a longer, larger vitola. His cigar habit is one of the most thoroughly documented associations of any public figure in the twentieth century.

John F. Kennedy

John F. Kennedy’s affection for Cuban cigars is well-documented, including the widely-reported story of him ordering a large stockpile before signing the embargo that would make future purchases legally complicated. The Kennedy-era cigar association tied the format to a specific kind of American elegance that persists in the cultural memory today.

Ulysses S. Grant

Grant reportedly smoked twenty or more cigars a day during the Civil War era, and the cigar became so central to his public image that admirers sent him boxes by the crate after his victories. Grant’s cigar habit belongs to an older America where the format was a staple of public and private life for men of a certain rank.

The Silver Screen Cigarette Era

Cigarettes carried a different but equally powerful visual tradition in the mid-twentieth century. The image of a cigarette in a black and white film is one of the most enduring compositions in cinema history, and the actors who established the visual language deserve mention in any honest catalog of famous smokers.

Humphrey Bogart

Bogart’s cigarette is a fixture of American cinema. Casablanca, The Maltese Falcon, and The Big Sleep all feature the cigarette as part of the character’s visual DNA. The Bogart cigarette became a shorthand for a certain kind of cool restraint that later actors have imitated for decades.

James Dean

James Dean’s cigarette imagery in Rebel Without a Cause and other films from his brief career built the mid-century cigarette icon for a younger generation. The imagery outlived him by decades and became a template for the rebellious young leading man in Hollywood.

John Wayne

John Wayne’s Westerns often featured cigarettes as part of the frontier setting, and Wayne himself was a public smoker for much of his career. The cigarette in a Western setting became its own visual convention, which Wayne helped establish more than most.

Musicians, Comedians, and the Cigar Presence

Frank Sinatra

Frank Sinatra’s public smoking spanned both cigarettes and cigars, and he was a fixture at cigar events throughout the peak of his career. The Rat Pack era, the Vegas years, and the after-hours culture Sinatra helped define all included smoke as part of the atmosphere.

George Burns

George Burns’ cigar was a signature. His public appearances well into his nineties almost always featured one, and his cigar habit became part of his comedic identity. Burns represented a generation of comedians who used the cigar not just as a habit but as a piece of stage business.

Groucho Marx

Groucho Marx’s cigar is one of the most iconic props in comedy history. It appeared with him in films, on television, and in his public appearances for decades. Along with the mustache and glasses, the cigar became inseparable from the character.

Modern Musicians and the Cigar

Rick Ross has been publicly associated with cigars throughout his career, and hip-hop culture has embraced the cigar as part of its visual iconography in a way that pop culture largely overlooks. Jay-Z has been photographed with cigars at multiple public appearances over the years. Snoop Dogg’s presence in the cigar conversation is broader than most, though his associations sit outside the scope of this article.

Where Al Capone Fits in the Modern Story

The modern cigarillo has found its own place in the culture that these earlier figures shaped. Al Capone Cigarillos is one of the brands that has carried the small-format tradition forward with real quality standards — hand-rolled Sweets and Jamaican Blaze lines wrapped in natural tobacco leaf and dipped in cognac and rum respectively, plus the Blues line built on an American Blend of Virginia, Oriental, and Burley tobacco with a natural silky leaf wrapper produced in-house.

The famous smokers whose images built the tradition were not smoking to be famous. They were smoking because the ritual fit the moment — a championship, an evening, a scene in a film, a private hour after a long day. The modern cigarillo delivers that same fit in a format that adapts to a life that moves faster than the classic hour-long cigar allows. The tradition is not gone. It has just adapted.

The Continuing Tradition

The list of famous people who smoke could stretch across dozens of pages. What matters more than the length of the list is what the list represents. A continuous cultural thread across sports, film, music, comedy, and public life that has adapted through every era it has passed through.

For the modern smoker looking to find their own place in that tradition, the format matters less than the intention. A championship cigar. A quiet evening cigarillo. A late-night cigarette in a black and white film scene. The ritual belongs to the person who chooses it, and it always has.

To explore the modern cigarillo lineup that carries the tradition forward, visit the Al Capone Cigarillos site or find a retailer near you.

This content is intended for adult consumers 21 years of age or older. This article is informational in nature and does not constitute medical or health advice. Preferences vary depending on taste and experience.