Quick answer: History's most famous cigar smokers include Winston Churchill (Romeo y Julieta), John F. Kennedy (H. Upmann Petit Upmann), Fidel Castro (Cohiba Lancero), Arnold Schwarzenegger (Punch), Michael Jordan (Partagas Lusitania), and Mike Tyson, who now has his own Gurkha-made line. Most of the classic favorites are Cuban, so US readers need the legal namesakes.
Pick almost any defining photo of the twentieth century and there is a decent chance someone in the frame is holding a cigar. Churchill flashing the V sign. Castro in fatigues. Jordan on the parade float. Cigar history runs straight through political and cultural history, and the brand choices behind those photos are better documented than most people assume. This guide covers the figures whose preferences trace to a named source, mostly Cigar Aficionado interviews and its 1999 Top 100 smokers list, and skips the claims built on repetition and guesswork.
One rule up front: this article does not endorse circumventing the US embargo on Cuban cigars. Where a favorite is Cuban, we point to the US-legal route instead.
Who Are the Most Famous Cigar Smokers in History?
The most famous cigar smokers in history, ranked one through three on Cigar Aficionado's 1999 Top 100 list, are Winston Churchill (Romeo y Julieta, an estimated 200,000 cigars in his lifetime), John F. Kennedy (H. Upmann Petit Upmann, 1,200 of them secured the night before he signed the 1962 embargo), and Fidel Castro (Cohiba Lancero, the brand created for him in 1966). Close behind sit George Burns (El Producto Queens, ten to fifteen a day to age 100), Mark Twain (roughly 22 a day), Sigmund Freud (about 20 a day), Arnold Schwarzenegger (Punch Punch), and Michael Jordan (Partagas Lusitania). The modern additions: Mike Tyson, whose Gurkha-made Tyson 2.0 Undisputed line launched in 2024, Jay-Z, who co-created the 2013 Cohiba Comador, and Joe Burrow, whose locker-room celebrations brought the victory cigar back to football.
Which Political Leaders Were the Biggest Cigar Smokers?
Winston Churchill (1874-1965)
No. 1 on Cigar Aficionado's Top 100, and it is not close. Churchill smoked an estimated 200,000 cigars across his life at a pace of eight to ten a day, and kept up to 4,000 in stock at Chartwell, his country home. His favorite marques were Romeo y Julieta and La Aroma de Cuba, the original Cuban brand whose name now lives on in a Nicaraguan revival. After his 1946 visit to Havana, Romeo y Julieta renamed its 7 x 47 Clemenceau the Churchill, which is why nearly every premium brand sells a Churchill today. The Churchill vitola guide covers the format's history and the best current picks.
John F. Kennedy (1917-1963)
The best cigar story in presidential history comes from Kennedy's own press secretary. By Pierre Salinger's 1992 account in Cigar Aficionado, JFK called him in one February evening in 1962 and asked for about 1,000 Petit Upmanns
by morning. Salinger came back with 1,200. Kennedy checked the haul, then signed the decree that made Cuban cigars contraband for everyone else. The H. Upmann name survives today in a US-legal Dominican version.
Fidel Castro (1926-2016)
Castro did not just smoke Cohiba. The brand was created for him in 1966, rolled at the El Laguito factory and handed out as diplomatic gifts for 16 years before the public could buy one in 1982. His pick was the Lancero, a 7.5 x 38 pencil of a cigar. He quit in 1985. Today Cohiba exists as two separate brands, one Cuban and one Dominican; the Cohiba brand guide untangles the two.
Which Writers and Thinkers Smoked Cigars?
Sigmund Freud (1856-1939)
Freud worked through about 20 cigars a day. Cigar Aficionado's Top 100 profile lists his brands as Don Pedros, Reina Cubanas, and small Dutch Liliputanos, not the grand Havanas people assume. He treated the cigar as a work tool.
Mark Twain (1835-1910)
Twain claimed roughly 22 cigars a day and was proudly cheap about it. Cigar Aficionado's Top 100 entry sums up his preference as anything except a Havana; he liked rough, inexpensive smokes and defended them in print. Every writer who keeps a box of value sticks on the desk works in his tradition.
Which Hollywood Stars Smoke Cigars?
Arnold Schwarzenegger
Arnold's cigar record is unusually well documented. He told Cigar Aficionado in his Summer 1996 cover interview that his future father-in-law Sargent Shriver handed him his first cigar in 1977, and he named the Cuban Punch Punch his favorite size: It's a good size for an after-dinner smoke or during the day.
By a 2021 Cigar Aficionado column his pick had shifted to the Partagas Serie D No. 4. As California governor he worked around his own smoke-free office by holding meetings in a courtyard smoking tent. The US-legal Punch brand carries the same name at everyday prices, and you can compare every Punch line across the retailers we track.
Demi Moore
Moore's Autumn 1996 Cigar Aficionado cover is one of the most reproduced cigar photos of the decade. Per the magazine, she had been smoking since 1989; its Top 100 list ranked her No. 52 and named the petite Montecristo Joyita among her picks. That cover marked the moment the 1990s cigar boom went fully mainstream.
Which Athletes Celebrate With Cigars?
Michael Jordan
Jordan is the most documented cigar smoker in sports. He told Cigar Aficionado in his November/December 2017 cover interview that he smokes up to six a day and that his favorite is the Partagas Lusitania, a 7.6 x 49 Cuban double corona. The habit started in 1991, when Bulls owner Jerry Reinsdorf handed him a cigar after a title win, and by 1993 he had a pre-game ritual of smoking a Hoyo de Monterrey double corona on the drive to home games. The Michael Jordan cigar guide breaks down the Lusitania and its US-legal stand-ins, and the US Partagas brand carries the name legally.
Mike Tyson
Tyson has been photographed with cigars for years, but in 2024 the habit became a product. Gurkha announced Tyson 2.0 Undisputed ahead of that year's PCA trade show: two blends, Habano and Maduro, made at the El Artista factory in the Dominican Republic, with MSRPs around $19 to $20. That makes Tyson one of the few names on this list you can match exactly and legally. Gurkha sits in our tracked catalog, and Cigars International stocks the Undisputed line.
Joe Burrow
Burrow revived the victory cigar for a new generation. After LSU won the national championship in January 2020, the locker-room celebration got so smoky that New Orleans police told players to put their cigars out or face arrest; the Superdome is a non-smoking building. Two years later he lit up again after Cincinnati won the January 2022 AFC Championship. No brand preference is documented; with Burrow the moment is the point, not the marque.
Which Entertainers Made Cigars Part of the Act?
George Burns
Burns smoked El Producto Queens, ten to fifteen a day, for roughly eight decades, and was buried at 100 with three of them in his breast pocket. The choice was practical. A tightly rolled Havana would go out under stage lights mid-routine, while the looser El Producto stayed lit through the act. He called the Queen my little lady.
Jay-Z
Jay-Z went further than smoking them. In 2013, General Cigar's Dominican Cohiba brand released the Cohiba Comador with him, a collaboration two years in development wrapped in a Connecticut Havana leaf that spent its final year of aging in Dominican rum barrels. The line has since been discontinued.
What Do These Famous Smokers Have in Common?
Three patterns hold across the list.
Cuban favorites, legal workarounds. Churchill, Kennedy, Castro, Schwarzenegger, and Jordan all favored Cuban cigars, which US residents cannot legally buy; the brief personal-use import allowance ended in September 2020. The practical route is the US-legal namesake, since Punch, Partagas, H. Upmann, Romeo y Julieta, and Cohiba all exist as separate US brands with the same names and different blends. The best Cuban cigars guide pairs every major Cuban marque with its closest legal stand-in, and the Cuban legality guide covers the embargo rules.
Rituals, not occasions. The most convincing habits attach to a repeated moment: Jordan's pre-game drive, Burns' stage act, Churchill's working day. Nobody here saved cigars for rare milestones. The cigar was furniture.
Documented beats assumed. The figures with named brands sat for interviews, mostly with Cigar Aficionado. Where that record does not exist, the honest answer is photographed, brand unknown,
and any list that hands every celebrity a tidy favorite deserves your suspicion. For where these marques stand today, the top 25 cigar brands ranking rates them on current quality and value.
Where Can You Try What They Smoked?
The US-legal versions of every brand above sit in our tracked catalog. Browse every cigar we track to compare live prices, or check active codes for Famous Smoke Shop before you order a namesake. Prefer a leather chair? The lounge directory covers cigar lounges across the US. And for the fictional end of the famous-smoker spectrum, the Tony Soprano cigar guide covers television's most analyzed smoker.
Frequently Asked Questions
Who is the most famous cigar smoker in history?
Winston Churchill. He smoked an estimated 200,000 cigars across his lifetime, topped Cigar Aficionado's Top 100 smokers of the twentieth century, and has a vitola named after him: the 7 x 47 Churchill, which nearly every premium brand now produces.
What cigars did Winston Churchill smoke?
Romeo y Julieta and La Aroma de Cuba, both Cuban marques of his era. After his 1946 Havana visit, Romeo y Julieta renamed its 7 x 47 Clemenceau vitola the Churchill in his honor. Today's US-legal Romeo y Julieta and the Nicaraguan La Aroma de Cuba revival carry both names forward.
Did Fidel Castro smoke cigars?
Daily, until he quit in 1985. The Cohiba brand was created for him in 1966 at the El Laguito factory and went on public sale in 1982. His documented favorite was the Cohiba Lancero, a 7.5 x 38 format.
What cigars does Michael Jordan smoke?
Partagas Lusitania, a 7.6 x 49 Cuban double corona. Jordan told Cigar Aficionado in his 2017 cover interview that he smokes up to six cigars a day and named the Lusitania his favorite. Earlier coverage documents a Hoyo de Monterrey double corona pre-game ritual dating to 1993.
Does Mike Tyson have his own cigar brand?
Yes. Tyson 2.0 Undisputed launched in 2024 through Gurkha in Habano and Maduro blends, made at the El Artista factory in the Dominican Republic, with MSRPs around $19 to $20 per cigar. Several major US retailers stock it.
Who smokes Cohiba cigars?
Fidel Castro is the brand's origin story; it was created for him in 1966. Arnold Schwarzenegger named Cohiba among his favorites in his 1996 Cigar Aficionado interview. Jay-Z partnered with the separate Dominican Cohiba brand on the 2013 Comador. The Cuban and US Cohibas are different companies.
Did Demi Moore actually smoke cigars?
Yes. Cigar Aficionado reported she had smoked since 1989 when it put her on its Autumn 1996 cover, and its Top 100 list included her at No. 52 with the petite Montecristo Joyita among her picks.
Are famous smokers' favorite cigars legal in the US?
The Cuban originals are not. The embargo has barred them since 1962, and the personal-use import allowance ended in September 2020. The same names (Cohiba, Partagas, Punch, H. Upmann, Romeo y Julieta, Montecristo) exist as separate US-legal brands, and Tyson's Gurkha-made line is fully US-legal.
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