The first users of tobacco are thought to have been the Mayan people of Central America who are believed to have smoked primitive forms of the cigar as early as 1000 BC. The first two Europeans to smoke cigars were Rodrigo de Jerez and Luis Torres, two of Christopher Columbus's crewmen during his 1492 voyage, who were said to have went ashore in Cuba and found natives smoking tobacco wrapped in corn husks. Columbus is credited for introducing tobacco to Europe on his return to Spain. Rodrigo de Jerez, who had taken to smoking, made the mistake of lighting up a cigar in public. His neighbors in Spain were so frightened by the smoke billowing from his mouth and nostrils that they alerted the Spanish Inquisition who imprisoned Jerez for his sinful and infernal habits. However, by the time he was released seven years later, smoking had caught on in Spain.

Eventually, an entire cigar industry evolved in Spain. Seville, Spain, the focal point of the industry, became known as the birthplace of the modern cigar. For years, Spain imported tobacco leaves from Cuba and assembled the cigars themselves. In 1821, Spain began allowing Cuba to manufacture cigars and Cuba became the leader in the cigar industry. In 1962, when Fidel Castro took over and the United States imposed a trade embargo against Cuba, many Cuban cigar makers moved their business to the Dominican Republic, Honduras, or Mexico. Thanks to the internet, one can still purchase a nice Cuban cigar fairly easily from places like Canada where there is no such embargo.

There are differences in opinion as to where the word 'cigar' may have originated. Some believe that the word 'cigar' may have derived from sikar, the Mayan word for smoking, while others believe the Spanish word 'cigarro' comes from 'Ciq-Sigan', the Mayan word for cigar. Others suggest that the Spanish word cigarro came from the word 'cigarra,' which is the Spanish word for cicada, due to its shape which is very similar to what is now called the perfecto.