The Upsetters Cigar: What to Expect From This Drew Estate Stick

Quick answer

The Upsetters is a full-bodied, distinctive cigar built around rare Jamaican Cow Tongue tobacco and a reggae-inspired story. Expect a bold, earthy smoke with a cultural backstory rather than a mild starter cigar.

Why The Upsetters stands apart from typical Drew Estate releases

The Upsetters is not a Drew Estate house blend in the usual sense. It was created by Nick Melillo, founder of Foundation Cigar Company, and it draws on Jamaica's cultural heritage and the rebellious spirit behind reggae music. That origin matters because it explains the blend's unusual identity: this is a cigar built around a place and a sound, not just a wrapper color.

The headline ingredient is rare Jamaican Cow Tongue tobacco, blended with premium tobaccos from other regions. If you are comparing it to the Connecticut-wrapped or sweet-tipped cigars you may have smoked before, the difference is intentional. The Upsetters is meant to taste unlike anything else on the shelf, so approach it as a new experience rather than a variation on a familiar profile.

The strength question: who should be cautious

The Upsetters is generally described as full-bodied, and the rare Jamaican leaf contributes to a dense, earthy character. That makes it a poor choice for a first cigar or for someone who prefers mild, creamy smokes. If you usually reach for Connecticut shades or lightly flavored cigars, this one will likely feel strong and dry by comparison.

A practical approach is to smoke it after a full meal and keep a sweet drink nearby. If you are new to fuller cigars, treat the first one as a tasting session rather than a casual everyday smoke, and pay attention to how the final third treats your palate.

Tasting notes to look for

Because The Upsetters incorporates Jamaican Cow Tongue tobacco alongside premium international leaves, the expected profile leans earthy, woody, and slightly spicy rather than sweet or creamy. You may notice dry cocoa, cedar, and a lingering mineral quality that reflects the Jamaican leaf. The exact experience will vary by size and how long the cigar has rested, so avoid treating any single tasting note as a guarantee.

The blend is designed to be distinctive, not crowd-pleasing. If you enjoy cigars that taste like a specific place and have a bit of roughness, that is the point. If you want a smooth, predictable profile, look elsewhere.

Sizes and what the absence of details means

The Upsetters is offered in multiple sizes, and size affects both burn time and intensity. A larger ring gauge tends to soften the edges and stretch the smoke, while a narrower vitola can concentrate the earthy notes. The catalog does not list specific wrapper, binder, or filler ratios beyond the Jamaican Cow Tongue component, so treat any exact blend claim you see elsewhere with skepticism.

That missing detail is a decision limitation, not a flaw. It means you should judge the cigar by the size you choose and your own tasting, rather than by a spec sheet.

The Upsetters FAQ

Is The Upsetters a Drew Estate cigar?

The Upsetters is often associated with Drew Estate because of its distribution and cultural ties, but it was created by Nick Melillo of Foundation Cigar Company. Treat it as a distinct project with its own identity, not a Drew Estate house blend.

How strong is The Upsetters cigar?

Expect a full-bodied smoke. The Jamaican Cow Tongue tobacco gives it a dense, earthy core, so it is best suited to experienced smokers or those who already enjoy fuller profiles. If you are new to full-strength cigars, start with a smaller size and a full stomach. Pair it with a sweet drink to balance the earthy finish.

What does The Upsetters taste like?

The tasting notes lean earthy, woody, and slightly spicy, with dry cocoa and cedar in the background. The rare Jamaican leaf contributes a mineral, rustic quality. Do not expect a sweet or creamy profile; this is a savory, distinctive smoke.

Which size should I choose?

Choose a larger ring gauge if you want a longer, slightly softer smoke; choose a narrower vitola if you want the earthy notes more concentrated. Since exact blend ratios are not published, let the size guide your first purchase rather than chasing a specific spec. Buy one size first, then compare before committing to a box.

Is The Upsetters a good gift?

It is a strong choice for a smoker who values story and rarity, especially someone interested in reggae culture or Jamaican tobacco. It is a poor gift for a beginner or someone who prefers mild cigars.

Product facts

• The Upsetters: Created by Foundation Cigar Company founder Nick Melillo and built around rare Jamaican Cow Tongue tobacco. The Foundation connection signals a boutique, culturally driven blend rather than a standard Drew Estate production cigar.