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The Top 100 Cigar Smokers of the Twentieth Century

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32 CHE GUEVARA Although he was asthmatic, Argentinian-born Che took up cigar smoking as one of his first Cuban customs. While serving as Fidel Castro's right-hand man during the Cuban revolution, he allowed himself two indulgences: books and cigars. But good tobacco was scarce in the mountains of Cuba, so any cigars they got were highly prized. After taking his share, Guevara used cigars as incentives for his soldiers because, as he wrote, "a smoke in times of rest is a great companion to the solitary soldier."  
33 CHARLIE CHAPLIN The perceived connection between cigars and wealth was one that actor-director Chaplin used to great effect in his films. Having survived a poverty-stricken childhood, Chaplin's sympathies were always with the underdog, famously symbolized in his character, the Tramp. Although the Tramp was not above picking up the cast-off cigar butts of the rich, in City Lights Chaplin used a big cigar both as a symbol of the upper class, with its wealth and power, and as a spear to harpoon it.  
34 ERNIE KOVACS The '50s TV genius smoked 20 Cuban double coronas a day, and his commercials with his wife, actress Edie Adams, for sponsor Consolidated Cigar's Dutch Masters and Muriel cigars are considered classics. Nothing about Kovacs, a TV writer, director, producer and star, was halfway: he lived extravagantly and worked so frenetically that he had shows on all four of the 1950s TV networks. When he died, his philosophy of excess was extolled on his tombstone: Nothing in Moderation.  
35 KING EDWARD VII "Gentlemen, you may smoke." With those simple words, spoken shortly after his coronation in 1901, Britain's Edward VII ended the tobacco intolerance that had marked Queen Victoria's reign. Yet Edward's pro-cigar stance was nothing new. In 1866, as the high-living Prince of Wales, he had quit his London gentlemen's club over its no-smoking policy (the final straw was when a servant admonished him for lighting up). He took 20 percent of the membership with him, and they soon established a club where smoking was heartily encouraged.  
36 DAVID LETTERMAN An on-again, off-again smoker, Letterman has brought cigar notoriety to late-night television. He would frequently sneak puffs from a double-corona-sized smoke during commercial breaks. Often the camera would catch him in the act, smoke rising past Letterman's face as he wore a "Who, me?" expression. Guests would arrive on his show bearing (Cuban) gifts, but few made more of an impact than Madonna, who in a 1994 appearance used a cigar and colorful language in a way that needed no clarification from Freud.  
37 EDWARD G. ROBINSON Short and squat with a bulldog face, Robinson didn't have leading-man looks. But in the 1930 film Little Caesar, Robinson not only launched his 50-year film career, but also set the stereotype of the American gangster forever in the minds of the moviegoing public. As Enrico "Rico" Bandello, Robinson portrayed a cigarette-smoking small-time hood who rises through the underworld ranks, becoming a Habanos-chomping, well-tailored mob boss before meeting his tragic end.  
38 DIZZY GILLESPIE The trumpeter renowned for his groundbreaking be-bop music couldn't afford good cigars during his early career, but decades later he avidly indulged in Cuban Hoyo de Monterreys and Romeo y Julietas. Gillespie long had an appreciation for things Cuban: Cuban trumpeter Mario Bauza befriended the young Diz during the 1930s, dramatically influencing his musical style. A decade later, Gillespie returned the favor, hiring the Cuban master congero Chano Pozo for his big band, helping to create Latin jazz.  
39 DANNY DeVITO After being turned on to cigars by Arnold Schwarzenegger, the actor-director-producer moved over the years from Cuban Cohibas to Partagas Serie D No. 4s, Diplomaticos and Bolivars. His favorite cigar coup occurred on a flight from Europe after filming The War of the Roses in the late 1980s, when he asked every passenger if they would mind if he smoked his cigar. He got their permission. "It was," he recalled, "the most enjoyable transatlantic flight I ever had."  
40 PETER FALK For TV buffs, the image is indelible: the rumpled police detective with the unruly hair and the wrinkled trenchcoat heads for the door, his back to the suspect. Then he pauses, taking a puff from his cheap cigar as he cocks his head to one side and says, "Just one more thing..." The murderer is as good as jailed. Like his "Columbo" character, Falk doesn't make any claims to being a cigar connoisseur. "I'll smoke anything anybody gives me," he once said. "I'm not particular."  
41 THOMAS EDISON Best known for bringing electric light and recorded sound into the world, Edison was also a prodigious cigar smoker. He liked to celebrate an invention with a stogie (preferably one he had won from a luckless lab assistant who had bet him he couldn't perform whatever feat of technological sorcery he was attempting). "The Wizard of Menlo Park" also had a sense of humor: to tweak associates who pilfered his cigars, he once planted phony smokes rolled from sawdust in his desk drawer.  
42 SYLVESTER STALLONE Somewhere between Rocky and Rambo lies Stallone the connoisseur. While most of his more famous on-screen personae do not suggest a reflective side, that is exactly what the private Stallone pursues in his love affair with premium cigars (paired with Armagnac or vintage wine). He's most nettled by acquaintances who cadge rare cigars only to let them go out after four or five puffs. We know the tough-guy thing is just for the movies, but do you really want him mad at you?  
43 H. L. MENCKEN American letters almost lost one of its most renowned champions of cigar smoking to, ironically enough, a cigarmaker. Mencken, journalist, humorist and shaper of modern fiction, toiled in his father's factory until August Mencken's demise allowed his son to pursue his true talent. He once took on a group of women who were seeking to prohibit smoking on streetcars, saying: "A woman who can stand half an hour of the Lexington fish market is well able to face a few blasts of tobacco smoke."  
44 DAN RATHER In a world of blown-dry newsmen anchored to their studio desks, Rather enjoys being out in the field, smoking a cigar. But he admitted that one of his smokes nearly killed an indoor plant that his wife had labored to keep alive. Almost caught by his wife sneaking a smoke indoors, he had stuck the half-smoked cigar in the plant's pot. It wasn't until he extracted the forgotten stub weeks later that the plant regained its health. Among Rather's most cherished smokes: cigars from Fidel Castro.  
45 CLARENCE THOMAS For those who fret over the hegemony of the Political Correctness Police (and who doesn't?), it is good to know that at least one confirmed cigar smoker sits on the Supreme Court. Thomas served as an assistant district attorney in Missouri, went into private practice for Monsanto, and later chaired the Equal Employment Opportunity Commission. George Bush nominated him in 1991 to replace Thurgood Marshall on the Supreme Court. He is occasionally seen at Cigar Aficionado's Washington Big Smokes.  
46 JOHN HUSTON Huston once described movie directing as "a left-handed form of human endeavor," and lived as though he tolerated his calling only as a way to finance his taste for the finer masculine endeavors, which famously included cigars, liquor, women and gambling. That outlook didn't stop him, however, from putting out some of the finest films ever made--The Maltese Falcon, The Treasure of the Sierra Madre, The African Queen--and almost single-handedly creating the film noir genre.  
47 ADOLPHUS BUSCH The beer baron who brought America the light, refreshing pilsner beer that became Budweiser was once dining in Paris with a St. Louis restaurateur named Tony Faust. Busch was trying to teach his friend to speak French by reciting the order to him; his tablemate then repeated it to the waiter. At the end of the meal, Faust turned to Busch and asked, "Now, how do we order the best cigars in the house?" When Faust repeated the request to the waiter, he was promptly presented with the bill.  
48 MEL GIBSON Even if Gibson were not a famous movie star, his name would be well known to habitués of some of the country's better cigar-friendly establishments--Club Macanudo, Grand Havana Room, etc. His name is etched there in brass on humidor boxes for all to see. The winner of the Best Director and Best Picture Oscars for Braveheart didn't mind risking his clean-cut image and rankling the Morals Police by announcing he would play a tobacco lobbyist in Thank You for Smoking.  
49 RUDOLPH GIULIANI As mayor of New York, Giuliani has focused on quality of life issues and watched crime rates plunge. The former U.S. attorney for the Southern District of New York has a sophisticated palate for cigars, preferring full-bodied smokes from the Dominican Republic and Nicaragua. He came upon his predilections after having been tutored in cigars by Ernesto Perez-Carrillo, maker of La Gloria Cubana. He is a frequent guest at Cigar Aficionado Big Smokes and enjoys cigars late at night.  
50 JOHN TRAVOLTA The actor who first came on the public's radar screen as Vinnie Barberino in TV's "Welcome Back, Kotter" and then skyrocketed to star stature as the disco-dancing Tony Manero in Saturday Night Fever has a long-standing affection for cigars. Some of his fondest memories are of his father smoking White Owls during his childhood in New Jersey. As a film star, Travolta can afford to reward himself with less pedestrian smokes: Davidoffs, Dunhills and Montecristos are his favorites.  
51 JOHN WAYNE The Westerns icon and Oscar winner for his performance in the 1969 classic True Grit smoked large custom-made cigars.  
52 DEMI MOORE Moore is partial to small cigars, such as the Montecristo Joyita, but also enjoys a Cohiba No. 2 or a Montecristo No. 2.  
53 LOU GERSTNER IBM's smoking chairman initiated a partnership with 21 states and school districts in which students benefited from the firm's technology and technical assistance.  
54 GEORGE S. PATTON Even while leading his troops into battles that liberated Europe in the Second World War, the brilliant but volatile U.S. general traveled with a humidor full of Cubans.  
55 GEORGE HAMILTON The actor smoked his first Cuban cigar at the age of 17 on the balcony of the Hotel Nacional in Havana, prior to the revolution. He later created his own brand.  
56 DUKE OF WINDSOR The former King Edward VIII in 1936 gave up his throne, but not his Dunhills, to marry an American divorcée.  
57 MARLENE DIETRICH The highest-paid actress of her time, the glamorous Dietrich was one of the first Hollywood sex symbols and was often seen on-screen with a smoke.  
58 THOMAS "TIP" O'NEILL At staff meetings, the House speaker would fill his closed office with smoke from his Churchills.  
59 DARRYL ZANUCK The Habanos-chomping 20th Century Fox mogul brought the world such memorable films as The Grapes of Wrath.  
60 DOUGLAS FAIRBANKS JR. The smoking screen legend's career spanned silent movies, sound pictures and TV, including the show "Douglas Fairbanks Presents."  
61 W. SOMERSET MAUGHAM The author who penned Of Human Bondage once wrote that the only resolution of his youth he kept was to smoke a cigar following lunch and dinner.  
62 ELVIS PRESLEY The king of rock and roll was immortalized on his own cigar last year, 21 years after his death.  
63 MILTON HERSHEY The famed candy maker smoked eight to 10 cigars a day, a habit he continued when he moved to Cuba to produce sugar.  
64 ALFRED HITCHCOCK The master of suspense, who gave us such thrillers as North by Northwest, Psycho and The Birds, was frequently seen with his trademark bowler hat and cigar.  
65 FIORELLO LA GUARDIA The New York mayor known for fighting corruption and organized crime generally left his cigar band on while smoking.  
66 TOM SELLECK One of the best times to smoke a cigar is while he's reading a script, says the former star of "Magnum, P.I." And one of the best cigars he smokes is a Montecristo No. 2.  
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