Jamaica has a deep-rooted tradition of embracing the underdog—the anti-hero who defies the odds. Upsetters are the rule-breakers, the game-changers, the ones who challenge convention. In the 1960s, Jamaica’s “rude boys” watched old spaghetti westerns, seeing themselves in gunslingers like Django, figures who stood tall against the establishment. It was this same rebellious spirit that gave birth to reggae music, a sound that shook the world.

The Upsetters cigar line is a celebration of Jamaican. At its core is the legendary Jamaican Cow Tongue tobacco, a rare and unique leaf cultivated in the very same hills where the indigenous Arawak people first planted tobacco centuries ago. The Upsetters honor Jamaica’s rich history, blending tradition with a bold new edge—because true pioneers don’t follow the rules, they rewrite them.

Dare To Be Different. Be an Upsetter.