6 Famous Cigar Aficionados


Cigars have always been a symbol of good taste, sophistication, and authority. This refined and elegant product is carefully crafted with selected dry leaves and sculpted like an artisan piece. So it’s no surprise that throughout the centuries, it has accompanied many famous cigar aficionados in the world who’ve established themselves as icons and cigar champions.

In this article, we’ll explore some of the most famous cigar aficionados of all time who were associated with the glamour and power of cigars. We’ll study their preferences and follow in their illustrious footsteps. So sit back and enjoy the discussion while puffing your favorite bundle of joy from Sigars.com.

1. Winston Churchill

This might not come as a surprise, but British Prime Minister Winston Churchill had to be on top of our list. Constructing his personal and political identity around the calm, authoritative air of cigars, he was a serial cigar enthusiast who’d stockpiled thousands of cigars throughout his life. Having spent time in Cuba as a young officer, he was introduced to the sport and later made it part of his public image.

In times of crisis or uncertainty, he’d routinely puff smoother cigars that would relax a whole room of anxious advisors. He used to smoke around 8-10 cigars per day-mostly Cuban brands-and was hardly ever seen without a cigar at hand during his time in office. Then, as he ascended the political scene, he made the cigar his emblem. In fact, he even amassed around 4,000 cigars at his home in a dedicated room. Talk about commitment! 

For the ultimate Churchill experience, try the Cubano, a Sigars exclusive that’ll keep you on your toes. With a smokey, pepper, rum, and vanilla profile, it’s a flavor trip!

2. Fidel Castro

Moving on with our list of famous cigar smokers, up next is Fidel Castro. His love for hand-rolled tobacco leaves was huge. Since 1953, the enigmatic revolutionary Cuban figure has been an avid smoker, always with a cigar at hand. In fact, he often offered cigars as gifts to foreign officials and diplomats and was living proof that cigars created an image of power and authority.

In fact, he was so associated with cigars that the CIA tried to assassinate him at one point by using an exploding cigar. Although he had to quit his 44-year-old habit, his passion for cigars never ended, and he often talked about how he dreamed of smoking cigars when sleeping.

Try the 2014 Pepper Cream Soda Habano Robusto for a sweet vanilla-based taste similar to Castro’s favorites.

3. John F. Kennedy

It’s funny how cigars can be common ground even for life-long enemies. John F. Kennedy shared the same cigar passion with Fidel Castro and, in fact, introduced a strict embargo banning all trade with Cuba. 

However, he secretly told his press secretary to stockpile his beloved Petit Upmann Cuban cigars within 24 hours before imposing the embargo. Quite a short notice, but the secretary did not disappoint as he managed to scrounge up to 1,200 cigars. Too bad the president didn’t have time to enjoy his collection before he was killed.

The 35th president of the United States was always down for some light to medium-flavored cigars. You can still enjoy celebrity cigar brands similar to his preferences or opt for the Xhaxhi Bobi – El Ingeniero with a profile of caramel, brown sugar, cream, and black coffee. Get a taste of what presidents taste!

4. Michael Jordan

Among the famous athletes who smoke cigars were Michael Jordan, a cultural icon and one of the best basketball players. He’d often smoke a cigar or two after a successful game with the Chicago Bulls and frequently smoked up to 5 cigars per day. But would his nonsmoking teammates ask the five-time league MVP to put out his cigar? Nope.

The NBA legend had a particular preference for Cuba’s most famous cigars, such as the glamorous Montecristo No. 2, also loved by Jay Z and Jack Nicholson. Additionally, he’s expressed fondness for the Partagas Lusitania, an earthly-flavored cigar. Find similar taste and equal glamour in the FX – Mayans M.C. Gordo with a profile of chocolate, paper, earth, and wood.

5. Al Pacino

Widely known for his role as Tony Montana in The Godfather, he’s a strong, masculine figure who never plays by the rules. He’s perhaps the biggest inspiration for men taking their first puff of cigars and a worldwide reference when it comes to cigar etiquette. Cigars were never a prop for him; they ultimately became a part of his personality and an extension of himself.

Although he’s never publicly endorsed any brand, the legendary actor has a particular preference for Cuban cigars. Paired with his favorite cognac, he’d always enjoy an intense tobacco taste with cocoa and cinnamon. Try the Foundry – Chillin’ Moose for a raisin, cocoa, and rye profile in a bold premium blend that’ll remind you of the iconic actor.

6. Sylvester Stallone

Our list of famous cigar aficionados in the world would not be complete without the American action film star Sylvester Stallone. Having embodied some strong male personalities in his movies, such as Rocky Balboa in the Rocky films and John Rambo in First Blood, he’s the epitome of strength and authority. Yet, he enjoys nothing but a love affair with good-quality cigars in his free time.

A high-profile fan of Dominican cigars himself, he doesn’t just love the cigars but also their history and community. With a particular love for vintage tobaccos with rich flavor, you’ll find him smoking something like the Arturo Fuente Don Carlos, a Dominican cigar with the dominant flavor of cedar.

Enjoy the Drew Estate Subculture – My Uzi Weighs a Ton for a cedar profile with hints of cocoa, leather, and dried fruit for a hearty, rich smoke Stallone would love.

Famous Cigar Smokers and Today’s Culture

Cigars will always be a symbol of influence, authority, and status. From iconic actors to famous athletes and politicians, cigar smoking has been associated with sophistication and power for centuries. We hope that this list of the most famous cigar aficionados of all time has inspired you to dig deeper into cigar history and the figures that represent it. 

Now it’s your turn to enjoy premium small-batch cigars delivered right to your door. Explore a wide selection today at Sigars.com and become part of the cigar aficionados gang!