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The Top 100 Cigar Smokers of the Twentieth Century

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So, how did we decide who deserved to be inscribed on a list of the century's most notable cigar smokers? Some of the choices were obvious. Of our top 10 picks, at least half were prodigious cigar smokers, lighting up 10 or more sticks a day, and one person, Mark Twain, was thought to smoke more than 20. Many of the people on the list are practically inseparable from a cigar, people you automatically picture with a smoke, such as Groucho Marx and Alfred Hitchcock.  
Other selections were less clear-cut. Some well-known personalities are more private about their cigar smoking, such as Harrison Ford and Clarence Thomas. And then there are aficionados who aren't necessarily household names but nonetheless have left their mark on the world, people like Al Lerner and Paul Volcker.  
Regardless of their status, everyone on the list shares one trait: the love of a good cigar  
1 WINSTON CHURCHILL Throughout his long life, Churchill nourished England with his battlefield bravery, political courage and prolific writing, and nourished himself with the best food, drink and cigars he could find. The man for whom the imposing Churchill cigar size is named smoked eight to 10 cigars a day, primarily Cuban brands. Not even the necessity of wearing an oxygen mask for a high-altitude flight in a nonpressurized cabin could prevent Churchill from smoking. As the story goes, the prime minister requested that a special mask be created that would allow him to smoke while airborne. Naturally, the request was fulfilled. On another occasion, Churchill hosted a luncheon for King Ibn Sa'ud of Saudi Arabia, who did not allow smoking or drinking in his presence. Rather than submit to the king's wishes, Churchill pointed out that "my rule of life prescribed as an absolutely sacred rite smoking cigars and also the drinking of alcohol before, after and if need be during all meals and in the intervals between them." The king was convinced.   Favorite cigar: Romeo y Julieta    
2 JOHN F. KENNEDY When you're the president of the United States, you can get just about anything you'd like. What the 35th president wanted in early 1962 was a bunch of Cuban cigars, 1,000 Petit Upmanns to be exact. He gave his press secretary, Pierre Salinger, less than 24 hours to round them up. Short notice for such a big request, but then JFK had a pressing reason for procuring the stash in such a timely fashion. He was about to sign an embargo prohibiting any Cuban products from entering the country, including his beloved cigars. The embargo was born of a nasty spat that the United States was having with Cuba and its fears that Fidel Castro represented a growing threat to America's security. But before Kennedy could act, he needed Salinger to complete his assignment. The press secretary didn't let him down, as he managed to scrounge up 1,200 cigars. Kennedy then signed the embargo, and Cuban tobacco has been off-limits to Americans ever since.   Favorite cigar: Petit Upmann    
3 FIDEL CASTRO Until he gave up the habit in 1985, the man who has ruled Cuba with an iron fist for 40 years was synonymous with cigars. Only a rising national concern over the health risks of smoking would lead to Castro's unequivocal decision to stop smoking cigars, even in private, to set an example for his people. Just because he abandoned a pastime that he had relished for 44 years doesn't mean he doesn't still think about cigars. He would occasionally dream that he was smoking a cigar, though he would admonish himself for doing so. "Even in my dreams I used to think that I was doing something wrong," he said in a 1994 Cigar Aficionado interview. "I was conscious that I had not permitted myself to smoke anymore, but I was still enjoying it in my sleep." Years earlier, when Castro and the rebels were plotting how to topple the Batista regime, the only time he did without cigars was when he ran out of them. Anticipating those infrequent occasions, he would hoard his last smoke, lighting it only to celebrate a victory or console himself over a setback.   Favorite cigar: Cohiba Corona Especial    
4 GEORGE BURNS From an impromptu singing gig in a candy store at the age of seven, to his enduring partnership with Gracie Allen, to solo stand-up comedy acts into his late 90s, Burns kept American audiences in stitches through most of the twentieth century. Invariably, he smoked his trustworthy El Producto cigars during his act, not because he couldn't afford a more expensive cigar, but because they stayed lit on stage longer than the more tightly packed Havana smokes. "If you have to stop your act to keep lighting your cigar, the audience goes out," he once cracked. The legendary star of vaudeville, radio, TV and film resurrected his movie career in the 1970s with starring roles in The Sunshine Boys and Oh, God! Burns, who lived to 100, credited his 10- to 15-cigar-a-day habit over a 70-year span with not only keeping him spry on stage but also with helping him outlive his physician. "If I had taken my doctor's advice and quit smoking when he advised me to," Burns quipped at age 98, "I wouldn't have lived to go to his funeral."   Favorite cigar: El Producto    
5 MARK TWAIN The author of The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn smoked at least 22 cigars a day, maybe as many as 40. Twain, née Samuel Clemens, supposedly once declared, "If smoking is not allowed in heaven, I shall not go." Twain's penchant for cigars didn't necessarily mean he smoked the best cigars. He knew that even his closest acquaintances were reviled by his stogie selections. Once, as he would later relate in his essay "Concerning Tobacco," he pilfered a handful of costly and elegant cigars from a friend's house, removed the labels, and placed the smokes in a box identified by his favorite brand. He then invited the man and 11 other friends over for dinner, offering each a cigar afterward. Everyone shortly excused themselves, and the next morning Twain found the cigars sprawled outside--except for the one left on the plate of the man from whom the cigars had been filched. "He told me afterward that some day I would get shot for giving people that kind of cigars to smoke."   Favorite cigar: Anything except a Havana    
6 MILTON BERLE Most men would be thrilled if their wives relished the smoke wafting from their cigars. Berle must be ecstatic, as all three of his spouses supported his hankering for Havanas. Even Marilyn Monroe, with whom the entertainer had a short fling before she became a star, savored the aroma of his cigars, and Uncle Miltie, who regularly tried to wean his friends off cigarettes and on to cigars, once bought a box of small cigars for the blonde bombshell, hoping to persuade her to switch. Berle's second wife, Ruth, not only supported his cigar habit, she showed ingenuity in doing so. During their honeymoon in Paris, Ruth went shopping for an evening bag, trying larger and larger sizes until she found one that could fit four of Miltie's mammoth Cubans. Before flying on to Rome, Berle packed some 500 Havanas, but customs officials there informed him that visitors were limited to 100 cigars. Nonplussed, Ruth pulled out a cigar from her bag and asked Berle for a light. "She nearly choked to death smoking it," Berle recalled, "but it enabled us to bring another hundred cigars in."   Favorite cigar: H. Upmann    
7 BILL COSBY There's something about winter that doesn't seem so funny to the man who has made millions laugh. In 1994, Cosby was watching the ladies' figure skating finals in the Winter Olympics on TV, puffing away on an Ashton. Suddenly, Tonya Harding began to cry during her routine. No, Nancy Kerrigan hadn't just blasted her with a bazooka; rather, the problem was a wayward shoelace. Mesmerized by the drama, Cosby took his cigar, which he had placed in an ashtray, and stuck it in his mouth--ash end first. His tongue told him he had "instantly made a very serious mistake." Two winters earlier, the comedian experienced another tobacco tribulation. As he walked about Manhattan with a cigar, the 38 degree chill "turned my warm, succulent corona into a piece of cold, soggy rutabaga." Stopping in a store that sold expensive gadgets for the Man Who Has Everything, as he described it, Cosby hoped to find some device that would keep his cigar warm. No such luck. "What kind of store was this?" he ruminated. "How could a man have everything if he didn't have a thing to keep his cigar warm?"   Favorite cigar: Ashton Maduro No. 60    
8 RED AUERBACH "I didn't want to rub anything in or show anybody what a great coach I was when I was 25 points ahead. Why? I gotta win by 30? What the hell difference does it make?" To Auerbach, sitting down on the bench to smoke a cigar in the waning minutes of a Boston Celtics triumph was his way of exuding humility. No one else saw it that way, though. To opposing fans, the "victory cigar" symbolized smugness in being able to administer such an awful beating to their team. Opposing players would be motivated by the cigar, doubling their intensity level until the final buzzer. Even Red's own players suffered from the fourth-quarter fumigation. According to guard Bob Cousy, the sight of Auerbach sitting calmly smoking a cigar only served to increase the fans' hostility and the abuse they heaped upon the Celtics. Auerbach's victory ritual was so reviled that the Cincinnati Royals management once handed out 5,000 cigars to its fans, instructing them to light up when the Royals won. Instead, the move backfired, as a fired-up Celtics squad blew the Royals off the court.   Favorite cigar: Hoyo de Monterrey  
9 JACK NICHOLSON The three-time Academy Award winner had been a longtime cigarette smoker when he took up golf in the early 1990s. He found himself smoking half a pack during a round to calm his nerves, so he decided to switch to cigars from around the fifth hole on. The change helped relax him, and eventually Nicholson got down to a 12 handicap. The actor first became enamored of Cuban cigars in 1973, when he was making The Last Detail, insisting that the petty officer character he played be a cigar smoker. The picture was shot in Canada, affording easy access to Havanas. When he resumed cigar smoking in the '90s, one of Nicholson's favorite haunts was the Forum in Los Angeles, where he would attend most of the Lakers' home games. At one time he was able to light up right on the arena floor, but as California antismoking laws got tougher, he found himself relegated to a hallway and, eventually, outside the building itself. "But I get around it," he said in 1995. "I sneak into the men's room at halftime, like when I was in high school, and take my drags there."   Favorite cigar: Montecristo    
10 BABE RUTH His larger-than-life persona, his considerable girth, and his zest for excess couldn't disguise the fact that George Herman Ruth was one of the best baseball players of the century. A standout pitcher for the Boston Red Sox before being traded to the New York Yankees, Ruth was the greatest slugger of his time, and perhaps of all time. Off the field, the Babe loved the good life: food, drink, women--and cigars. While still in Boston, he invested in a local cigar factory that produced nickel smokes with his picture plastered on the wrapper. "I smoked them until I was blue in the face," he once lamented. On a road trip, he snuck a woman into the room he was sharing with Ernie Shore, a fellow Red Sox pitcher (who once combined with Ruth to pitch a perfect game against the Washington Senators). Not surprisingly, Shore couldn't sleep, as the sounds emanating from the Babe's bed were hard to shut out. The next day, Shore noticed four or five cigar butts next to a sleeping Ruth. The Babe's explanation later: "Oh, that! I like a cigar every time I'm finished."   Favorite cigar: "Babe Ruth" perfecto    
11 AL CAPONE One of America's most notorious gangsters was about to board a train for prison, having been nailed for tax evasion. During the Roaring Twenties, Capone had controlled gambling, prostitution and bootlegging rackets. Despite his propensity for violence, the Chicago crime boss saw himself as a generous benefactor, someone who provided jobs for thousands and served "decent liquor and square games." As he was led to the train in 1932 after losing his appeal, Capone bade adieu to his freedom by lighting a cigar.  
12 GROUCHO MARX A cigar sometimes got the comedian into trouble. Once, his third wife, Eden, objected to his "stinky old cigar" and ordered him to extinguish it or get a new wife. On an earlier occasion, Marx splurged for a 10-cent pure Havana after spotting an advertisement that promised "thirty glorious minutes in Havana." When the cigar lasted only 20 minutes, Groucho demanded a replacement. Somehow, each subsequent cigar met the same fate, until after the fifth one the merchant wised up and tossed Groucho out.  
13 BILL CLINTON Does he or doesn't he? The 42nd president is known for chewing cigars on the golf course, but there have been only a few reports of his actually smoking a cigar. It's well known that the first lady bans tobacco smoke from the White House, but does the chief executive light up somewhere else--say, for instance, on a state visit overseas? Perhaps if Hillary makes her way to the Senate, she'll entrust her husband with the authority to set the smoking regulations in their new home in New York.  
14 MICHAEL JORDAN When the NBA legend made a move on court, few opponents could stop him. Off the court, it was much the same way. Case in point: Jordan would be smoking, say, a Cuban Montecristo No. 2 on the Bulls' bus. Would any of his nonsmoking teammates ever ask the five-time league MVP to snuff out his cigar? As former teammate John Salley once put it: "We were just apostles. Jesus was smoking, that's all there is to it. What are you going to say?"  
15 ARNOLD SCHWARZENEGGER It never hurts to have a father-in-law who smokes cigars. Sargent Shriver, the father of Schwarzenegger's wife, Maria, the TV correspondent, offered him a cigar after a dinner, shortly after Schwarzenegger and Maria met in 1977. Now, any complaints Maria might make about her husband's cigar smoking can be parried with a quick reference to her dad. "You can always say, 'Look, honey, your father wouldn't have introduced me to something that's bad,' " the ex-bodybuilder once cracked.  
16 RON PERELMAN When the multimillion dollar businessman and former owner of Consolidated Cigar Corp. wants to eat out, he naturally looks for a cigar-friendly establishment. As he explained in a 1995 interview, "I think I pretty much gravitate toward restaurants that allow cigar smoking, partly because it's so important to me to smoke, particularly after dinner. But from a purely financial point of view, if somebody is not going to support my business, I'm certainly not going to support their business."  
17 FRANCIS FORD COPPOLA The director of such films as The Godfather and Apoca-lypse Now owes his cigar education, in part, to Jack Warner, the onetime head of Warner Bros. As a young writer and director, Coppola worked a bit with Warner, who taught Coppola the proper way to light a cigar. When Warner died, he left a gold-and-silver cigar cutter to an associate, who gave it to Coppola. Warner had gotten the cutter from Lord Mountbatten, the British admiral who was assassi-nated in 1979.  
18 RUSH LIMBAUGH The outspoken radio and TV commentator was a latecomer to cigars, but he was a quick learner. Starting out with Macanudos, Ashtons and Fonsecas, Limbaugh soon gravitated toward Havanas. On a trip to London, he became acquainted with Punch Double Coronas, Partagas Lusitanias and Monty No. 2s, but, alas, he couldn't find any Hoyo de Monterreys. The disappointment was short-lived, however; on a yachting holiday, he found a rare box of Hoyo Double Coronas on St. Maarten.  
19 WHOOPI GOLDBERG If there's anyone who's hard to pigeonhole, it's Goldberg. She has been nominated for an Oscar for her performance in The Color Purple and been named best supporting actress in Ghost. Her screwball stand-up routines are renowned, but she has also hosted a talk show in which she explored serious subjects. She's just as difficult to classify when it comes to cigars. While she prefers small cigars, she's been known to light up a big Cohiba now and then.  
20 AL LERNER This Montecristo No. 2 connoisseur was given the unenviable task a decade ago of turning around MBNA Corp., a Maryland bank saddled with underperforming real estate loans. Lerner began to pay down debt and took the parent company public, and today it is one of the nation's biggest credit card issuers. Part of MBNA's success is due to Lerner's introduction of affinity credit cards, which benefit the group issuing them. A football fan, Lerner bought the new Cleveland Browns last year.  
21 RUDYARD KIPLING The Nobel Prize-winning English writer and poet was hailed in Britain as the heir apparent to Charles Dickens. He is best known for tales that relate to British imperialism in India, such as The Jungle Book (1894) and Kim (1901). Despite being admired, Kipling was criticized by many of his peers for his support of British colonialism and racial prejudice. The cigar-loving author is also famous for saying, "A woman is a woman but a good cigar is a smoke."  
22 ZINO DAVIDOFF "If your wife doesn't like the aroma of your cigar, change your wife," said the late Swiss-based cigar-industry icon, who began his illustrious career in the 1930s as a worker in his father's tobacco shop in Geneva. The Russian émigré was instrumental in creating the high-end Hoyo de Monterrey "Chateaux" series of cigars and launched his signature line of Cuban smokes in 1970. He was the author of The Connoisseur's Book of the Cigar, widely regarded as the bible of the industry.  
23 J. P. MORGAN The legendary business tycoon and robber baron was a painfully shy and private person. But in his professional dealings, John Pierpont Morgan was ruthless. During his long career as head of J.P. Morgan & Co., he helped save the U.S. government from bankruptcy (at a price) and helped to create U.S. Steel. He loved to travel, collect art and smoke cigars, of which he consumed dozens a day. He was known to favor Cuban smokes, particularly Meridiana Kohinoors.  
24 SIGMUND FREUD The father of psychoanalysis saw phallic symbols everywhere, but nevertheless conceded that "sometimes a cigar is just a cigar." He began smoking at 24, enjoyed an average of 20 cigars a day, and was rarely photographed without his tobacco companion. He often stated that he couldn't work without cigars and that "smoking was one of the greatest pleasures in life." A lifetime smoker, he favored Don Pedros, Reina Cubanas and Dutch Liliputanos.  
25 BRUCE WILLIS Willis, who first gained attention as the wisecracking David Addison on ABC's "Moonlighting," has electrified worldwide audiences in a number of big-budget blockbusters that usually have him, if not saving the world (Armageddon), then saving the day (the Die Hard trilogy). He has demonstrated a flair for comedy as well, as shown in The Player. During the mid-1990s, Willis frequented Arnold Schwarzenegger's Monday night cigar dinners at Schatzi on Main.  
26 MICHAEL DOUGLAS The award-winning actor-producer has a proclivity for playing flawed heroes and antiheroes. Douglas received an Academy Award for Best Picture as producer of the 1975 film One Flew Over the Cuckoo's Nest and won a Best Actor Oscar for his portrayal of a corporate high roller in Wall Street. He also starred in Romancing the Stone, The War of the Roses and everyone's favorite cautionary tale on the dangers of adultery, Fatal Attraction. He enjoys smoking Montecristo No. 2s on the golf course.  
27 W. C. FIELDS Fields had a successful career playing hard-drinking, hard-living, yet lovable misogynists in such films as Tillie and Gus (1933), My Little Chickadee (1940) and Never Give a Sucker an Even Break (1941). The bulbous-nosed, nasal-voiced comedic actor started out as a vaudeville juggler, teaching himself the skill with cigar boxes. An occasional cigar smoker, Fields used cigars as props in many of his movies to make him "look boorish," according to biographer James Curtis.  
28 HOWARD COSELL The polysyllabic TV sports journalist was a fixture on ABC's "Monday Night Football" telecasts. Known for his blunt and often harsh rebukes--in his words, "telling it like it is"--of athletes and fellow sportscasters, Cosell was both loved and hated by viewers and peers alike. And Cosell wouldn't have had it any other way. He wasn't averse to bumming cigars off the same colleagues he often ridiculed, according to writers H. Paul Jeffers and Kevin Gordon.  
29 ORSON WELLES When he was just 25 years old, Welles conceived, wrote and directed Citizen Kane (1941), considered by many cineastes to be the finest and most innovative American film ever made. The larger-than-life cinema icon, who went on to produce four more masterpieces, was at turns reviled and revered by his peers. Welles was a lover of the good life, especially fine cigars; he intentionally wrote cigar-smoking characters, such as Touch of Evil's police captain Hank Quinlan, into his films.  
30 HARRISON FORD The reluctantly hunky Hollywood heavyweight has been dubbed "Star of the Century" for his reign as the all-time top box office draw. Revered for his honest and moral on-screen presence, Ford has appeared in an eclectic mix of films such as the Star Wars trilogy, Witness and Clear and Present Danger. A member of the $20 million-per-picture club, Ford shies away from the Hollywood scene, preferring the company of his family on their large Wyoming ranch, where he can puff in peace.  
31 TOM CRUISE The star of Top Gun, Mission: Impossible and Eyes Wide Shut has been a cigar aficionado throughout most of the 1990s. A scene for his 1996 hit, Jerry Maguire, was filmed at the Grand Havana Room in Los Angeles. During the middle of the decade, Cruise reportedly had a standing order for Cuban Cohibas with London and Geneva tobacconists. He and his wife, actress Nicole Kidman, once presented their friend, Demi Moore, with a travel humidor for her birthday.  
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."  
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