Top 5 Most Famous Cigar Smokers in History

Cigar smoking has long been associated with sophistication, glamour and power, so it’s no surprise that some of the most famous, and infamous, figures in history and popular culture have enjoyed a quality cigar. We’ve put together a list of our favourite celebrity cigar lovers, along with their cigar preferences, so that you can light up knowing that you are following in their illustrious footsteps.

Winston Churchill

The most familiar photographs of this 20th century British prime minister almost always feature him puffing on a cigar. His taste for cigars was first piqued during the time he spent in Cuba as a young military officer in 1895.  Later, as he ascended the political ranks, the cigar became a deliberate and considered part of his public image. During his time in office, he was rarely seen without one in hand, whether he was posing on the steps of Number 10 Downing Street, or chairing a cabinet meeting. He unabashedly proclaimed that “I drink a great deal. I sleep a little, and I smoke cigar after cigar”.

The cigar brand most closely associated with Churchill is the Havana based company Romeo Y Julieta, whose most famous and popular cigar is still named after him. The Romeo Y Julieta Churchill comes in a short and a wide variation, as well as its classic form, and is known for its balanced and aromatic blend of selected leaves from the Vuelta Abajo region.

Fidel Castro

Cuba’s enigmatic revolutionary leader was an avid smoker of the cigar, of course one of his homeland’s biggest exports. Even though he eventually gave up his 44 year long habit, Castro’s passion for cigars never left him. Long after he quit, he spoke about how he still dreamed about smoking cigars while he slept at night.

During his time as leader of Cuba, he famously often chose to give foreign officials and diplomats cigars as gifts. In fact, his association with them was so well known that the CIA attempted to assassinate him using an exploding cigar. But even earlier in his life, as a young rebel planning to overthrow the Batista government, Castro was often spotted (and photographed) puffing on his favourite variety of Cuban cigar, Cohiba Corona Especiales. Two of Cohiba’s filler leaves, the seco and ligero, experience a third fermentation in barrels, which gives the blend its distinctive silkiness.

John F. Kennedy

Most famous for his glamorous image, rumours of an affair with Marilyn Monroe, and of course his dramatic assassination, 35th President of the United States John F. Kennedy shared his passion for cigar smoking with one of his greatest enemies, Fidel Castro. In fact, when in September 1962 he introduced a strict embargo which banned all trade with Castro’s Cuba, he secretly told his press secretary, Pierre Salinger, to stockpile more than 1000 boxes of his favourite Petit Upmann cigars, produced by Cuban brand H. Upmann, before the ban came into place. 

You can still enjoy cigars from President Kennedy’s preferred supplier today; H. Upmann are known for their light to medium flavoured cigars, which are some of the most popular and well known in the Cuban market. Unfortunately, there wasn’t much time for JFK to enjoy his private collection before he was killed in November 1963. 

Michael Jordan

Michael Jordan is an American cultural icon who brought huge international popularity to the NBA during the 1980s and 1990s and is believed by many to have been the best basketball player of all time. But did you know that he’s also been known to enjoy smoking cigars? Photographers, and his team mates, would often spot him indulging in a cigar on the bus during his successful stints with the Chicago Bulls from 1984 to 1993 and from 1995 to 1999. In the documentary The Last Dance, it was revealed that Jordan would frequently smoke up to 5 cigars a day. His Bulls teammate John Salley once joked about Jordan’s cigar habit, saying no one on the team would ever ask him to put out his cigar, because “we were just apostles. Jesus was smoking, that’s all there is to it. What are you going to say?”

Jordan’s preferred cigars are two of Cuba’s most famous. On a number of occasions he has been seen smoking the glamorous Montecristo No. 2, which is one of the most recognisable cigars in the world. It’s also a favourite among other celebrity cigar smokers such as Jay Z and Jack Nicholson. Alongside the Montecristo, Jordan has also expressed his fondness for the deep earthy flavour of the Partagas Lusitania.

Sylvester Stallone

The Golden Globe winning American action film actor Sylvester Stallone found stardom by bringing to life some iconic characters in film franchises, including boxer Rocky Balboa in the Rocky films, First Blood and its sequels, in which he played military veteran John Rambo, and his series The Expendables. Stallone is another high profile cigar fan. Famous for playing the tough guy, Stallone’s distinctive look and voice have landed him many high profile movie roles, and a reputation with audiences all over the world. But, in his free time he enjoys nothing more than a good smoke.

Stallone has described how he doesn’t just enjoy the cigars themselves, but also the history and community surrounding cigar-smoking. He has also said that he is a particular fan of Dominican cigars. You can follow his example by indulging in some of the finest Dominican smokes, such as the Arturo Fuente Don Carlos cigar, which uses hand selected vintage tobaccos for a rich flavour.