Blind Review: Drew Estate Undercrown ShadyXX

I’m sure all are familiar with the rap sensation Eminem so there is no need to school you on those particulars. However in case you don’t know, Paul Rosenberg is the president of Shady Records which is Eminem’s record label. Rosenberg is a cigar enthusiast who collaborated on two projects with well known Jonathan Drew of Drew Eastate. The first project was a 15th anniversary cigar for the record label with a tweaked blend of the Undercrown brand. Once again these two giants of their respective industries came together for a 20th anniversary cigar which is the same size and blend as their initial release. Not knowing any of this prior to smoking I was I extremely satisfied to see how well the project went.

Blend Specifics

  • Cigar Reviewed: Drew Estate Undercrown ShadyXX
  • Wrapper:  Mexican San Andres
  • Binder:  Stalk Cut Habano 
  • Filler:  Nicaraguan, Brazilian
  • Size: 5” x 50 Belicoso

Appearance & Construction

The ShadyXX is a box pressed cigar that wears a dark toothy wrapper with minimal veins. It’s an impressively rolled belicoso with an excellent capped pointed head. As I squeeze the cigar, it is packed with tobacco with no soft spots to be found. The overall size and appearance is inviting to smoke.

Flavor and Smoke Characteristics

Using my Palio cutter I clip a small cut on the head of the cigar and take a few dry puffs. Flavors of dried fruit and earth resonate on the draw. As I light the ShadyXX, the resistance is just right and delivers black pepper quickly followed by cocoa powder. Shortly into the cigar, a creaminess emerges along with espresso and a minty finish. On the retrohale there is wood, earth and anise. The ShadyXX produces a nice amount of smoke and the interplay of oak and cocoa play strong at this point.

About halfway through the ShadyXX the creaminess returns with espresso echoing on the palate. Another retrohale gives a blast of pepper with citrus that is surprising considering the taste and mouthfeel at first. At this point there are some interesting complexities to the cigar. The white and gray ash is not too firm but it holds on. As the smoke progresses, more coffee notes along with cream and vanilla resonate to a long finish.

In the final third of the ShadyXX, flavors of maple, nutmeg and creamy espresso begin to develop. Unfortunately even with the nuances picked up the Undercown yields a short finish which becomes almost bitter. And despite smoking the cigar slow the bitterness persists. The black pepper returns, albeit in not as intense a fashion as in the beginning of the smoke.

As the ShadyXX reaches its end some oakwood and vanilla finish it up on a fine note. A pleasant little cigar with a medium to full profile all the way through.


After finding out what the cigar was it’s exciting to hear it was a project that went so well. Having had the pleasure of meeting Jonathan Drew on many occasions for near two decades I can say he is a generous soul and an innovator, so I can see why people would want to collaborate and create a cigar with him. Many collaborations from persons outside the cigar industry can come off as more of a status symbol than a quality undertaking. This is not the case with the Undercrown ShadyXX as the blend is well crafted and the tobaccos top notch. They are sold out most places but if you can get your hands on some you will be fortunate and pleased with the experience.