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Cigars are often presented as stereotypical rich man's accessory. Cigars are often smoked to celebrate good fortune, like the birth of a child, a graduation, a big business accomplishment, etc. Some buy and keep a cigar 'for luck' with regard to a bet, with the intention of smoking it after winning the bet. The expression "close, but no cigar", said after a near miss derives from that tradition.

King Edward VII enjoyed smoking cigarettes and cigars, much to the chagrin of his mother, Queen Victoria. After her death, legend has it; King Edward said to his male guests at the end of a dinner party, "Gentlemen, you may smoke." In his name, a line of inexpensive American cigars has long been named King Edward.

MARK TWAIN The author of The Adventures of Tom Sawyer smoked at least 22 cigars a day, maybe as many as 40. Twain, declared, "If smoking is not allowed in heaven, I shall not go."

Two men who died during the zenith of the cigar's popularity owing ultimately to nicotine addiction and the consequent cancer were President Ulysses S. Grant of the USA (throat cancer) and Dr. Sigmund Freud (mouth cancer). Both these men were noted for regularly smoking an entire box (20 cigars) a day. For Freud, the decision not to smoke was surprising, even illogical. Indeed, one can hardly think of Freud, father of psychoanalysis, without thinking of cigars.

Although Grant was able for the duration of the Civil War to stop drinking, he was most often seen with a cigar and after his Presidency, Grant contracted cancer. Not wishing to leave his wife Julia penniless, Grant decided to write and publish his memoirs while in great pain.

Karl Marx the philosopher and Groucho Marx the comedian were both heavy cigar smokers. When Groucho was ill with appendicitis, his brother Zeppo stood in for him onstage. Apparently, few people noticed the difference, but Zeppo admitted that the cigars he had to smoke made him sick.

Karl Marx once claimed that the amount of money he received for the first volume of his monumental "Capital" never paid even for the cigars he smoked when working on it.

Fellow Vaudevillian George Burns also smoked cigars as part of his "shtick." Comedians have often used cigar smoking as part of their comic timing.

Famous quotes about the cigar include not only Freud's but also from a Rudyard Kipling poem: "A woman is only a woman: but a good cigar is a smoke." Also: "What this country needs is a good five cent cigar." The cigar was also a staple for vaudeville jokes and slapstick, from the overexcited new father who says "have a baby, my wife just had a cigar" to the exploding cigar which may have been a coded proletarian gesture of resistance to the cigar, which with the top hat and tails was the semiotic for "capitalism" in the early 20th century.

There is a huge collection of poetry in favor of cigars. “THE CIGAR” BY THOMAS HOOD describes his passion for cigar. Is seems it’s the only thing that really matters in life “No matter - I can wait, so I have my cigar”.

In the movies, cigars have been big forever. In the lacerating 1967 war flick The Dirty Dozen, Ernest Borgnine smokes a cigar with sublime satisfaction when he is holed up in a bunker during war games in England. No one else smokes anything but cigarettes in the film. Borgnine is a two-star general, the highest-ranking officer in the film.

In Stalag 17, P.O.W. JJ Sefton admits that he trades cigarettes with the Germans because he has no need for them; he only smokes cigars

Arthur Daley, played by George Cole, in the U.K. comedy drama series Minder was often found puffing on a cigar. In one episode, he was unknowingly hypnotised out of enjoying them, and spent the rest of the episode searching for a brand that he would enjoy.

American actor George Peppard was an avid cigar smoker, most prominently in the series The A-Team, where it was his character, "Hannibal" Smith's trademark.
In the 1983 film Scarface, Tony Montana often smoked cigars during scenes that showed him moving up in the cocaine underworld.

In the 1992 film Scent of a Woman, Lt.Col Frank Slade, who is staying in a posh New York hotel, orders his assistant Charlie Simms to get him a Montecristo No.1, knowing that it will take time to find one. Actually he is planning to shoot himself, so he wants Simms to leave him alone for some time.

Several storylines in the 1990s sitcom Seinfeld revolve around or pay regard to a box of Cuban cigars in season 4. Cigars rolled by Dominicans were part of a storyline on a season-8 episode. In addition, Kramer was an avid cigar smoker on the show; often seen smoking whether or not it was a part of an episode's plot.

Since apart from certain forms of heavily cured and strong snuff, the cigar is the most potent form of self-dosing with tobacco, it has long had associations of being a male rite of passage, as it may have had during the pre-Columbian era in America. Its fumes and rituals have in American and European cultures established a "men's hut"; in the 19th century, men would retire to the "smoking room" after dinner, to discuss serious issues.

Famous jazz musicians, most notably Miles Davis, were proud cigar smokers, appreciating their fine flavor & aroma, though never did they smoke on major stage. According to Davis, his favourite brand was Augusta, a rare brand only sold in restaurants & coffee shops, or directly to certain famous people, like Davis.

Radio host Don Geronimo is and avid cigar lover. He has spoken at length about his love of cigars, especially the rare Fuente Fuente OpusX. Geronimo is one half on the nationally syndicated Don and Mike Show.

Radio host Ron Bennington is an avid cigar smoker, and has espoused so on many occasions on the Ron and Fez Show.

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