Brand Heritage
The Upsetters is a boutique cigar brand that draws its identity from the rebellious spirit of ska and reggae culture, channeling the raw, unapologetic energy of Jamaica's original rude boy movement into a line of boldly crafted smokes. The brand has cultivated a loyal following among cigar enthusiasts who appreciate cigars with personality and attitude to match their tobacco. With roots in Nicaraguan production, The Upsetters has positioned itself as a counterculture voice in the premium cigar world, offering accessible yet characterful blends for smokers who want something a little outside the mainstream.
Blend & Construction
The Original Rude Boy Gordo is a Nicaraguan-made infused cigar presented in a 6 x 60 Gordo vitola — a wide-ring, generously proportioned format that delivers a cool, slow burn and an expansive draw. As an infused offering, the blend incorporates additional flavoring layered over what is, in keeping with the line's Nicaraguan origin, a foundation of Central American tobaccos. Specific wrapper, binder, and filler leaf details are not publicly disclosed by the brand, but the infused nature of the cigar suggests the tobaccos are selected to serve as an approachable, smooth canvas for the added flavoring notes. The large 60-ring gauge construction allows for a voluminous, creamy smoke output throughout the session.
Flavor Profile
In keeping with the infused character of The Original Rude Boy line, smokers can expect a smooth, sweetened smoke experience that leans mild to medium in body. The wide Gordo format contributes to a cooler burn temperature, which helps the infused notes come through cleanly without harshness. The overall experience is approachable and even-keeled, with sweetness present from the first light through the final third. Complexity is modest by design — this is a cigar meant to be enjoyed rather than dissected, offering consistent, easygoing smoke character that makes it particularly inviting for those new to infused cigars as well as seasoned smokers seeking something relaxed and unpretentious.
Recommended Pairings
Alcoholic: A golden rum such as Appleton Estate Signature Blend complements the sweetened, smooth profile of this infused Nicaraguan smoke beautifully, echoing its warmth without overwhelming the palate.
Non-Alcoholic: A medium-roast café au lait or a creamy iced coffee pairs naturally with the mild sweetness, softening the tobacco character and extending the pleasant finish between draws.
Best Enjoyed
The Upsetters Original Rude Boy Gordo is ideally suited for casual, unhurried settings — a backyard gathering, an afternoon on the porch, or a relaxed weekend session where time is on your side. The 6 x 60 Gordo format delivers an estimated smoke time of 60 to 90 minutes, making it a satisfying long smoke without demanding intense focus. Thanks to its infused, approachable character, it is an excellent choice for novice and intermediate smokers, though experienced cigar enthusiasts who enjoy a laid-back infused option will find plenty to appreciate as well.
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