Cigar Lifestyle

The Cigar Advisor Playlist: Volume 5

Reading Time: 6 minutes


The only thing that’s more diverse than the contents of our collective humidors, are the songs we bob our heads to as we cruise to and from work each day. Whether it’s an antiquated tape deck or cd player, the latest and greatest streaming service, or just plain old DJ-driven radio, almost all of us play something to serve as the soundtrack to our lives. The Cigar Advisor Playlist ups the ante and pairs these songs with our favorite cigars.

In this edition, along with our regular submissions, we’ve added a pick from master blender, Michael Giannini, of Ventura Cigars. He’s an avid music fan, too, so we picked his brain for his favorite pairing.

As always, we remind you that our selections are subjective and may not always be on par with what you prefer. We implore you to send us your picks, and if we love it, we just might feature YOU in an upcoming edition.

How Can You Pair Music with Cigars?

There’s two ways to listen along:

  • Download the official Spotify Cigar Advisor Playlist (it’s FREE!)
  • Watch the embedded videos while reading in real time.

In Volume 5, we are featuring cigars from Ventura Cigars, Hoyo de Monterrey, Aganorsa Leaf, and Crowned Heads. Check ‘em out!

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Michael Giannini’s Pick

“Eclipse” – Pink Floyd

Album: Dark Side of the Moon
Release Year: 1973
Genre: Classic Rock/Progressive Rock

Cigar Smoked While Listening:

Archetype Chapter 3: Dawn of Destiny Robusto

Size: Robusto (5” x 50)
Strength: Medium Plus (listed Medium)
Wrapper: Ecuador Sumatra
Binder: Nicaragua
Filler: Nicaragua

music and cigars cigar advisor playlist Archetype Chapter 3 Dawn of Destiny Cigars at Famous Smoke Shop

About The Cigar:

I love that it has a Sumatra wrapper on it with Nicaraguan tobaccos. It reminds me of the days working with Ernesto-Perez Carrillo 20 years ago. He would drop little Christmas gifts of cigars he was working on, and to be able to recreate that this year with him and bring me back to 20 years ago…this just reminds me of that.

Why They Pair Well:

What I love about “Eclipse,” it just tugs at your soul because it’s about life. If you listen to the words, it’s about what you create and what you destroy. It’s about things that you shouldn’t do in your life. But I’ve always been a fan of space and when I was a kid we landed on the moon and this year was the 50th anniversary of that. We’re still exploring space and we’re eventually going to Mars. I’d like to go there and grow tobacco because nobody’s ever done that. Every time I listen to the song, it just tugs at my heart.


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Jared’s Pick

“I Am the Highway” – Audioslave

Album: Audioslave
Release Year: 2002
Genre: Alternative Rock

Cigar Smoked While Listening:

Siboney Reserve by Aganorsa Leaf Lonsdale

Size: Lonsdale (6” x 44)
Strength: Medium Plus (listed Medium)
Wrapper: Nicaragua Corojo 99 Jalapa
Binder: Proprietary Nicaragua
Filler: Proprietary Nicaragua

music and cigars cigar advisor playlist Siboney Reserve by Aganorsa cigars at Famous Smoke Shop

About The Cigar:

A Famous Smoke Shop exclusive, Siboney Reserve is made by Aganorsa Leaf at their TABSA factory in Nicaragua. While most of it entertains at the medium-body mark, the strength will creep up on you slowly. It doesn’t cross the threshold into full territory, but the brawn is there. Its smoke is dense, robust, and is accompanied by wafts of cedar, black pepper, nuts, and a graham cracker-like sweetness on the finish. While I enjoy that it’s both complex and cops a bit of an attitude at times, I love even more the smooth and easy-to-enjoy profile it exhibits throughout. It’s just a simple, balanced ride of flavor to stand as a solid evening puffer.

Why They Pair Well:

Many parallels are drawn. The gentle ambience of the song’s introductory swells mirror Siboney’s gradual complexity. Deep lyrics and a bottom end enhanced by baritone guitar sit in sync with the cigar’s strength. “I am the Highway” is an easy listener. It’s perfect for cranking up when out on the road, but it’s the type of tune that will have you digging deeper into the accelerator when you get lost in it. I don’t often smoke in the car, but I could see myself doing it in this case. The song and the cigar are equal parts powerful and smooth, both to my palate – and my ears.


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Gary’s Pick

“La Comparsa” – Chucho Valdés

Album: New Conceptions
Release Year: 2003
Genre: Jazz

Cigar Smoked While Listening

Hoyo de Tradición Toro

Size: Toro Box-Press (6″ x 52)
Strength: Medium
Wrapper: Honduras Jamastran Viso Rosado
Connecticut Habano
Filler: Honduras San Augustin, Dominican Piloto Cubano, Nicaragua Ometepe

music and cigars cigar advisor playlist Hoyo de Tradicion cigars at Famous Smoke Shop

About The Cigar

The Hoyo de Tradición Toro has been one of my personal medium-bodied cigar favorites for years thanks to its creamy, sweet, and spicy flavor profile. Released in 2007 as an homage to Hoyo de Monterrey’s Cuban heritage, the Toro is gently box-pressed in a blond, mid-priming Honduran Jamastran Rosado wrapper garnished with a Cuban Hoyo de Monterrey band. (That band is also one of my favorite things about the cigar.)

Looking at the Hoyo’s blend, it may appear to be very spicy. What’s remarkable is how it maintains an even keel throughout offering caramelized flavors of cedar, nutmeg, almonds, sweet tobacco, and an evocative floral aroma. And although this Hoyo is markedly different from its Cuban cousins, it offers a rich, creamy, and thoroughly relaxing smoke that any fine premium cigar, Cuban or otherwise, would envy.

Why They Pair Well

Translating to “The Group” in Spanish, La Comparsa showcases the prodigious talents of four-time GRAMMY and three-time Latin GRAMMY winner, Chucho Valdés. Known to jazzbos as one of Cuba’s finest jazz pianists, Chucho’s cover of this popular Cuban tune offers plenty of syncopated montuños, choppy chord changes, and frenetic scales.

What makes this pairing just about perfect is, both Valdés’s performance and the Hoyo Tradición share a wealth of complexity. However, the result is something equally tranquil and captivating. Pour yourself a Daiquiri, and while you relax to La Comparsa, it’s easy to imagine the sounds, flavors, and aromas that once graced the walls of Havana’s famed El Floridita bar in its heyday.


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John’s Pick

“Blackberry” – The Black Crowes

Album: Three Snakes and One Charm
Release Year: 1996
Genre: Rock

Cigar Smoked While Listening:

Crowned Heads La Imperiosa Dukes

Size: Robusto (5 ½” x 54)
Strength: Full
Wrapper: Ecuador Habano Oscuro
Binder: Nicaragua
Filler: Nicaragua

music and cigars cigar advisor playlist Crowned Heads La Imperiosa cigars at Famous Smoke Shop

About The Cigar:

“Hey Blackberry, how you taste so sweet…”

Boy, does it. To me, a mouthwatering berry sweetness is La Imperiosa’s most noticeable quality: it first shows itself in the pre-light, and never quits. Other flavors – leather, creamy spice, wood – come along to complement it, and its chocolatey aroma…and it only gets more savory from there, pouring on a ton of rich flavor with a sweet, salty finish.

Meaning “the imperative,” it’s pretty much how the Crowned Heads boys felt about the Las Calaveras 2014 LE – it was absolutely necessary that they bring back that My Father-made blend, given the high demand.

Why They Pair Well:

This is my favorite cut off the album because it has such a juicy groove…this is the Crowes getting back to their R&B roots (think “Hard to Handle”, which is probably what turned you on to the band in the first place). The vibe is laid back, but when all the parts come together – this tune just oozes a buttery-rich layer of funk that’s just spicy enough.

La Imperiosa drops that same kind of big and bold-feeling profile, especially in this fat n’ juicy size. And just like the sweet groove in “Blackberry”, offers a bit of kick – but never gets out of balance.

Crowned Heads meets the Black Crowes for a smoke that’s sweet and savory all around – and a great way to spend 90 minutes of your time.

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Paul Diver
4 years ago

Love the advisor ! Where’s the Z-Man ??

Jared Gulick
4 years ago
Reply to  Paul Diver

He’s no longer with the company.

Cigar Advisor Staff

Cigar Advisor Staff


The Cigar Advisor Staff is comprised of three good-humored, yet dangerously unpredictable writers who share over 60 years of premium cigar smoking experience. Traversing the tobacco landscape like smoke-shrouded Avengers, they wander (mostly because the fat one ate the map) in search of new leaf adventures armed with nothing but torch lighters and runcible spoons as their weapons. Each is equally knowledgeable on the matters and pursuits of the cigar lifestyle, with his own unique and capricious insights on various luxury, sports, automobiles and entertainment affairs - all served with good counsel for your reading pleasure.

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