Whenever we see someone smoking a cigar, we know it’s not just an indulgence; it’s a symbol. But of what? Traditionally, the cigar has been cultural shorthand for sex, power, wealth and American masculinity. But throw in blurred gender lines, an increasingly health-obsessed society and the crosswinds of legalization, and things get more complicated.

Although they had been in the United States since long before the country itself existed, cigars really took off after the Civil War (thank you, Ulysses S. Grant) and hit their peak at the turn of the 20th century. They remained popular until President John F. Kennedy imposed an embargo on Cuba in 1962—the day after he had his press secretary scour Washington, D.C. for 1,000 H. Upmann Cuban cigars.

As American mores loosened up, the gendered component of cigars became inescapable. Unlike cigarettes, cigars were never successfully marketed to or adopted by women. To this day, women are rarely shown smoking cigars, and when they are, they’re portrayed as unfeminine—except for the effortlessly cool bombshells who can hang with the guys. Picture Seinfeld’s Elaine Benes blowing smoke with her feet propped up on her editor’s desk, or Dita Von Teese posing as a classic Hollywood pinup seductively holding a cigar.

Of course, cigars are undeniably phallic, which is only reinforced by the image of a bunch of guys man-spreading around a smoky lounge full of dark wood and leather furniture, puffing away without a woman in sight. Other times it’s more literal: Cigars play a supporting role in the Starr Report, which details sexual encounters between President Bill Clinton and Monica Lewinsky. In one such instance, a cigar literally subs for a penis—which, as we learned, does not meet the Clintonian definition of sexual relations.

Today, with legalized marijuana getting all the attention, weed cigars have come along to appease those who want the classiness of a cigar as well as the heady benefits of cannabis. And with President Barack Obama’s 2016 lifting of the Cuba embargo, it’s possible we’re about to witness a cigar renaissance—one that eschews macho symbolism and leans toward the small batch, the handmade, the simple reconnection with pure pleasure. Meanwhile, as long as there are weddings, newborns and NBA championships to celebrate, cigars aren’t going away anytime soon.


TOUR THESE CIGAR FACTORIES

Real Fábrica de Tabacos Partagás. Alamy

TABACALERA DE GARCÍA, DOMINICAN REPUBLIC
Take a look behind the scenes at the largest handmade-cigar facility in the world, where visitors learn about the entire process—from the properties of the tobacco leaves to the quirks of the final product.

REAL FÁBRICA DE TABACOS PARTAGÁS, CUBA
Visit one of Cuba’s most famous cigar factories (pictured below), dating back to 1845. Partagás spans five floors in a historic and architecturally stunning building in Old Havana.

LA CORONA, CUBA
Not only can you tour this massive multistory operation, but visitors are encouraged to ask questions and interact with employees.

TABACALERA SANTIAGO, NICARAGUA
One of several cigar factories in Nicaragua owned by Cubans who escaped during the revolution, Santiago offers free tours and puffs of the merchandise along the way.

ON SITE CIGARS, UNITED STATES
Visitors to this Miami institution get the full sensory experience, starting with Cuban coffee and concluding with a complimentary cigar, Cuban soft drinks and traditional pastelitos and croquetas.

J.C. NEWMAN CIGAR COMPANY, UNITED STATES
The last remaining cigar factory in Tampa’s Ybor City area houses a museum of cigar history. Brands produced here include Diamond Crown, Brick House and El Baton.


MORE LIFESTYLE CONTENT FROM PLAYBOY:

**An Idiot’s Guide to (Newly Legal) Cuban Cigars**

An Idiot’s Guide to (Newly Legal) Cuban Cigars

**The Golden Age of the Martini**

The Golden Age of the Martini

**A Situational Guide to Recreational Marijuana**

A Situational Guide to Recreational Marijuana