From Churchill’s War Rooms to Hollywood backlots, cigars have been companions to history’s boldest characters. Some used them as a signal of victory, others as a stage prop, a thinking aid, or a simple pleasure after dinner. What unites them is the ritual: the cut, the light, the first aromatic draw. Here’s our curated roll call of famous cigar smokers — the people you can’t picture without a cigar — and the smokes that made them legends.
The Definitive 25
1) Winston Churchill (UK) — The Bulldog with a Box
- From the War Rooms to Chartwell, cigars were as constant as his prose. He even commissioned an oxygen mask that allowed smoking in-flight.
- Signature Smoke: Romeo y Julieta Churchill.
2) John F. Kennedy — Last Call Before the Embargo
- Dispatched Pierre Salinger to secure 1,200 petit H. Upmanns… then signed the 1962 Cuban embargo.
- Signature Smoke: H. Upmann Petit Upmann.
3) Fidel Castro — El Jefe
- Quit in 1985 to set a public example, but dreams of cigars persisted.
- Signature Smoke: Cohiba Corona Especial.
4) Groucho Marx — The Comedic Prop
- The cigar was part of the punchline—and the persona.
- Signature Smoke: Budget Havanas in his early days; later varied.
5) Mark Twain — Prolific Puffing
- 20+ a day and the immortal line: “If smoking is not allowed in heaven, I shall not go.”
- Signature Smoke: “Anything except a Havana,” he joked.
6) George Burns — Timing Is Everything
- Favoured El Producto because they stayed lit on stage.
- Signature Smoke: El Producto.
7) Red Auerbach — The Victory Cigar
- Lighting up on the Celtics bench became a sporting taunt and tradition.
- Signature Smoke: Hoyo de Monterrey.
8) Jack Nicholson — Lakers, Golf, Cigar
- Navigated LA’s smoking rules with mischief worthy of McMurphy.
- Signature Smoke: Montecristo.
9) Babe Ruth — Big Swings, Big Smokes
- Invested in his own branded perfecto and celebrated… enthusiastically.
- Signature Smoke: “Babe Ruth” perfecto.
10) Al Capone — Parting Puff
- Boarded the prison train with a cigar lit. Image: indelible.
- Signature Smoke: Varied.
11) Bill Clinton — The Chewer
- More often chewed than smoked; golf-course sightings abound.
- Signature Smoke: Off-record; mixed reports.
12) Michael Jordan — Air and Ember
- Montecristo No.2 on the team bus; who’s telling MJ to stub it out?
- Signature Smoke: Montecristo No.2.
13) Arnold Schwarzenegger — Monday Night Smokes
- From Schatzi on Main to the Governor’s Mansion.
- Signature Smoke: Broad Havana tastes.
14) Zino Davidoff — The Retailer as Royalty
- Authored The Connoisseur’s Book of the Cigar; helped shape modern luxury cigar culture.
- Signature Smoke: Davidoff (Cuban era), Hoyo “Châteaux”.
15) J. P. Morgan — Finance and Fire
- Dozens a day; favoured Cuban Meridiana Kohinoors.
- Signature Smoke: Meridiana Kohinoor.
16) Sigmund Freud — Sometimes…
- “Sometimes a cigar is just a cigar.” Also: 20 a day.
- Signature Smoke: Reina Cubana, Don Pedro, Liliputanos.
17) King Edward VII (UK) — The Royal Green Light
- Broke the Victorian ban; membership walked with him to a smoking-friendly club.
- Signature Smoke: Dunhills and fine Havanas.
18) Rudyard Kipling (UK) — A Smoke Is a Smoke
- Noted for the quip, and for tales steeped in Empire.
- Signature Smoke: Various Havanas.
19) Alfred Hitchcock (UK/US) — Suspense with a Stogie
- Bowler hat, deadpan delivery, and a cigar never far away.
- Signature Smoke: Dunhill / Havana.
20) Orson Welles — Larger Than Life
- Wrote cigar-smoking characters into his films on purpose.
- Signature Smoke: Rich Havanas.
21) Francis Ford Coppola — Cinematic Rituals
- Inherited a cutter with lineage from Lord Mountbatten via Jack Warner.
- Signature Smoke: Classics across Cuba.
22) Che Guevara — Two Indulgences
- Books and cigars—even with asthma. Used them as battlefield incentives.
- Signature Smoke: Scarce war-time Havanas.
23) Peter Falk — “Just One More Thing…”
- Columbo’s cheap cigar became a character in its own right.
- Signature Smoke: Inexpensive coronas.
24) Thomas Edison — The Practical Joker
- Celebratory stogies; decoy sawdust “cigars” for office pilferers.
- Signature Smoke: Robust domestics and Havanas.
25) Duke of Windsor (UK) — Abdication, Not Abstinence
- Gave up the throne, not his Dunhills.
- Signature Smoke: Dunhill.
Honourable Mentions (quick hits)
- Bill Cosby — Ash-first mishap on live TV; Ashton Maduro No.60.
- Milton Berle — Packed 500 Havanas for Paris; H. Upmann.
- Harrison Ford — Prefers peace and puffing on the ranch.
- Marlene Dietrich — Glamour with a cigar before it was “a thing.”
- Ernest Hemingway — Endorsed by Zino himself as a Havana devotee.
- Pierce Brosnan (UK/IE) — Bond off duty at London’s Monty’s cigar club.
- Tom Selleck — Reads scripts with a Monte 2.
- George S. Patton — Humidor in the field; Cubans across Europe.
- Rudy Giuliani — Tutored by Ernesto Perez-Carrillo.
- Whoopi Goldberg — From small cigars to an occasional big Cohiba.