Perhaps it's because there's a close cultural connection between great music and smoky bars. Anyone who knows anything about jazz knows that its truly legendary improvisers - Coltrane, Bird, Miles Davis, Dizzy Gillespie - cut their teeth playing in bars so smoky that it's a good thing everybody was too busy improvising to need sheet music.
Or maybe it's because both cigars and music are contemplative pleasures. A casual smoker can get a quick tobacco-fix from a cheap cigarette, just as a casual music listener can enjoy the background hum of pop songs on the car radio. But to really enjoy a great performance, or a good tobacco, sitting still and paying attention are necessary.
In any case, music and cigar smoking seem to belong together, and some of the most famous musicians are (or were) cigar devotees - just as, it turns out, one of the most famous of cigar devotees is also a musician. Avo Uvezian, the maker of Avo cigars, is also a respected classical and jazz pianist, a Julliard graduate, and even the one-time official pianist of the Shah of Iran. After a successful musical career based first in his native Middle East, and then in the contiguous United States, Uvezian moved in the 1980s to Puerto Rico, where he opened a restaurant and bar and dabbled in cigarmaking. After customers at his Puerto Rico restaurant told him how much they enjoyed some cigars he'd had rolled himself, from a blend of tobaccos he hand-picked, he opened his own Dominican Republic-based cigar factory, working with noted cigar maker Hendrik Kelner. Now his company makes three million cigars a year, and Uvezian himself still makes music - his first CD, Legacy, was released in 2004.
For another example, consider the great trumpeter Arturo Sandoval, who smokes, by his own estimation, four or five cigars a day. Music allowed the Cuban-born Sandoval to rise to fame in his native Cuba - and to defect from that country in 1990, during a long stint playing concerts in Europe (he now lives in Florida). Sandoval has played the horn for Lionel Hampton and Dizzy Gillespie, Gloria Estefan and Johnny Mathis, Michel Legrand and Frank Sinatra. His technically flawless playing has resulted in his being the kind of musician whose work is often known by people who couldn't name him - he is brought in as a session musician by some of the world's finest and best-known (see above), and he often scores movie soundtracks. As his work with the BBC Symphony Orchestra and the Leningrad Philharmonic prove, he's even proved able to handle the rigors of classical music as well as jazz - sometimes doing both in the same concert.
The cigar-music connection is especially strong in Cuba, known as one of the world's cigar capitals. Both cigars and music are staples of island life (the cigar remains one of the island's most prominent exports), and the strength of both in Cuban culture depends partly on the nimble and intelligent blending of elements from everywhere - wrappers and fillers from different parts of Latin America, rhythms and melodies from the African coast, South America, US pop, Western European classical, etc. In other words, Cuban cigarmaking and Cuban music have both survived, and flourished, by mixing and melding.
For generations, cigar rollers were entertained by the sound of paid musicians or by music from the radio. (This tradition continues even now in the Dominican Republic, where workers at the Arturo Fuente factory, among other places, are treated to the work of performing musicians.) With this tradition in place, it's no wonder that some of Cuba's music legends got their start as cigar-factory entertainers; and since tobacco smoking has been a part of Latin American life far longer than it has in some other places - Columbus's sailors noted it being smoked in what is now modern Cuba in the year 1493, so there's many more centuries of lore to draw on its psychological and emotional associations are deeper and richer, providing better material for songwriters to mine. Thus famous Cuban songwriter Beny More, himself a former entertainer for the cigar-factory workers, touches on the song in a number of his classic compositions.
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