Hey friends! Let’s talk about the Django from Foundation The Upsetters Cigars, a line inspired by the rebellious “rude boy” culture of 1960s Jamaica. These urban youths, rocking out to ska music, shaped a subculture in Kingston that led to some notorious gangs like the Charles Street Spanglers and Pheonix Skull.

The Original Rude Boy

Check out the Original Rude Boy’s robust 6 x 60 Gordo size, all wrapped up in a stunning brown Maduro wrapper. But the real adventure starts on the inside, where you find Jamaican cow tongue leaf and a wild technique called “Caribbean atmospheric herbal fusion.” It’s a flavor journey that’s anything but ordinary.

Nick Melillo, the brain behind Foundation Cigars and former EVP at Drew Estate, knows his stuff when it comes to unique cigars. He started Foundation in June 2015, right in the heart of Connecticut’s tobacco fields.


A Quick Brand Overview

From their first hit, El Gueguense, to the elegant Highclere Castle, Foundation has quickly built an impressive portfolio. Their HQ sits on a 50-acre tobacco field in Connecticut, but their seeds start in the rich soils of Estelí, Nicaragua.

Now, let’s dig into the ancient Jamaican tobacco strain with The Upsetters Cigar Original Rude Boy in our latest review.

Cigar Specs

  • Country of Origin: Nicaragua
  • Strength: Full
  • Wrapper: Maduro
  • Binder: Nicaragua
  • Filler: Jamaica / Nicaragua
  • Available Sizes: Original Rude Boy (6 x 60)

Cold Draw

The Rude Boy sports a vibrant band with green, red, and yellow against a dark backdrop, featuring a gunslinging man with dreadlocks. It’s a well-rolled cigar emitting a floral aroma with hints of clove.

I snipped it with my guillotine cutter for some pre-light puffs—herbal, earthy vibes coming through strong.

First Third

As the flame meets the foot, a mix of honeysuckle sweetness and spicy clove kicks in. The complexity keeps you guessing, with notes of citrus and pepper making occasional appearances. It’s a sweet start that doesn’t overpower.

Second Third

The richness of the Jamaican and Nicaraguan fillers starts to shine through now. You’ll notice cocoa, earth, and toast with a sweet tip that’s subtly herbal. It’s a testament to Melillo’s expertise with infused cigars, offering a twist on the usual tobacco flavors.

Final Third

The pepper ramps up as we near the end, but the balance is spot on. Warm, aromatic hits of allspice, toast, and Turkish coffee mix with a touch of orange sweetness.


The Upsetters Cigar Original Rude Boy isn’t just a sweet cigar; it’s a masterful blend of Jamaican and Nicaraguan tobacco that’s medium-full in strength. It’s a relaxing smoke that respects Jamaica’s rich tobacco history. If you love a unique blend of sweetness and spice, this cigar is definitely worth a try. It’s out of this world!

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