Cigar Lifestyle

The Cigar Advisor Playlist: Volume 3 (Woodstock Edition)

Reading Time: 8 minutes

On August 15, 1969, a stampede of music fans tore through the quiet, unassuming town of Bethel, New York. They had gathered there for the most storied, mud-soaked music festival of all time…Woodstock.

The production was originally planned to be held in Wallkill, NY, but the townsfolk had other plans. On July 2, with only a month and a half left until showtime, Wallkill passed a law that banned the concert from their city limits.

About two weeks later, Max Yasgur offered his 600-acre dairy farm as a venue. Even with a new location secured, problems with vendors, bands, and other logistical nightmares arose. The final stroke of bad luck was realized just two days before the event. Instead of the estimated 50,000 concertgoers that were expected to arrive, the organizers were seeing numbers closer to 200,000. They simply weren’t prepared to sell tickets to that many people and wouldn’t have been able to enforce the masses from getting in without them, so the decision was made to make entry free.

Word spread quickly, and it’s estimated that more than a million people made the pilgrimage toward Bethel, with about 500,000 making it there it to experience the spectacle. Many thousands were turned away by police – the highways into town had turned into parking lots. Many of Woodstock’s attendees abandoned their cars, opting to walk the final miles to the show in lieu of trying to wait out the traffic.

It’s surprising that it even happened. But it did, and for many American audiophiles, there’s no greater historical example of musical expression. One thing is certain. Legends were born in its wake.

2019 marks Woodstock’s 50th anniversary, so we’ve decided to celebrate it with this special edition to our monthly Cigar Advisor Playlist feature.

If you haven’t seen our previous iterations, each of us pairs a song with a cigar and detail why we think they play well together. Some are contrasting, others are complementary, and at times, they’re even both.

With each volume, the playlist expands, and our aim here is to give you a pairing, not of food or drink, but one that is oft forgotten: the element of sound.

There are two ways to listen along:

We hope our picks strike a chord in you, but kindly remember…as with cigars, and everything else, our taste in music is subjective. If our choices don’t get you into the groove, add your picks in the comments below.

Track 9

Tommy’s Pick:

“White Rabbit” – Jefferson Airplane

Album: Surrealistic Pillow
Release Year: 1967
Genre: Psychedelic Rock

Cigar Smoked While Listening:

Diesel Whiskey Row Rabbit Hole

Diesel Whiskey Row Rabbit Hole

Size: Toro (6” x 54)
Strength: Full
Wrapper: Ecuador Habano
Binder: Mexican San Andres
Filler: Nicaragua Condega, Jalapa, and Ometepe

About The Cigar:

I’ve really grown to love this AJ Fernandez-made cigar and for several reasons. First off, it’s medium-bodied and smooth as silk as each draw lets off a huge amount of sweet-smelling smoke. While the 5-year aged wrapper and Nicaraguan fillers are a perfect blend of flavorful tobacco, it’s the San Andres binder that’s aged in Rabbit Hole Bourbon barrels that gives this tasty treat its character. Before it’s even lit it gives off a slight bourbon aroma and upon firing up, the sweetness and woodiness is right there. There are elements of cocoa and even a smack of brown sugar on the palate and it’s one of those sticks that just gets better with every puff.

Why They Pair Well:

Jefferson Airplane was a huge draw at Woodstock where they performed White Rabbit, written by lead singer, Grace Slick. The song is based on the Adventure of Alice in Wonderland, (mentioning a number of its characters), but this top ten Billboard hit is about tripping on pills and was written after an acid trip… The references to Alice being ten feet tall are about changing sizes after popping pills and drinking an unknown liquid. I think that liquid could have been Rabbit Hole Bourbon being consumed on the lawn at Woodstock while puffing away on a Diesel Whiskey Row while flashing peace signs to every passer-by. The cigar has a naturally sweet, mellow calming effect when I smoke it, something I believe the members of Jefferson Airplane would have grooved on.

Track 10

Gary’s Pick:

“Soul Sacrifice” – Carlos Santana

Album: Santana Legacy Edition
Release Year: 2004
Genre: Classic Rock

Cigar Smoked While Listening:

Acid Cold Infusion

Acid Cold Infusion

Size: Lonsdale (6 3/4” x 44)
Strength: Medium
Wrapper: U.S. Connecticut Shade
Binder: Nicaragua
Filler: Nicaragua

About The Cigar:

Rolled in a U.S. Connecticut Shade wrapper, the Acid Cold Infusion presents an herbal-infused, Nicaraguan core without the fragrance intensity of some of the other Acid cigars. The draw is effortless, and the medium-bodied smoke is ultra-creamy, revealing an ample supply of floral notes, plus sweet, toasty, woody, and fruity flavors. As one of the most relaxing cigars in the Acid line-up, Cold Infusion is also the most accessible choice for smokers who would prefer to ease their way into the Acid Cigars culture.

About the Song:

This Santana track is the live, 11-minutes and 49-second Woodstock performance of “Soul Sacrifice” that appears on the Santana (Legacy Edition), a 2-CD set released in 2004. When Santana took the stage at Woodstock, they were a relatively obscure jam band from San Francisco. During their set, Santana nailed it. The audience of 250,000 went wild and talk about timing – less than two weeks after the festival, Santana’s self-titled debut album was released on August 30, 1969 and a new rock star was born.

As the story goes, Carlos Santana played the set while tripping on a tab of LSD given to him by Jerry Garcia. Carlos took it, figuring that by the time the band went onstage many hours later, it would wear-off. Due to scheduling foul-ups, Carlos was told the band had to go on sooner, which turned out to be shortly after he took the tab. Yet, despite all that, Santana turned in a legendary performance, clearly illustrating Carlos’s focus and talent as a premier guitarist.

Why They Pair Well:

OK, so I went with the obvious for this one, and chose an Acid cigar (ha-ha). The Cold Infusion may not echo the intensity of the track, but I like the counterpoint between the cigar and the song. Moreover, the cigar’s fragrance may remind you of things like incense and patchouli oil that were associated with the hippie counterculture of the late 1960s. “Soul Sacrifice” grooves along smoothly, much like the Cold Infusion, with some interesting fits and starts along the way. Once they settle down to business, both the cigar and the song nimbly move ahead, turning in a well-focused and satisfying performance.

Track 11

John’s Pick:

“Wooden Ships” – Crosby, Stills, Nash & Young

Album: Crosby, Stills & Nash
Release Year: 1969
Genre: Classic Rock

Cigar Smoked While Listening:

Oliva Serie V Melanio

Oliva Serve V Melanio

Size: Torpedo (6 ½” x 52)
Strength: Full
Wrapper: Ecuador Sumatra
Binder: Nicaragua
Filler: Nicaragua

About the Cigar

The Oliva story starts in Cuba, where Melanio – the family patriarch, and namesake to this smoke – began growing tobacco in the late 1800s. The family would work their land for two generations, before being forced off the island amidst the shock of Castro’s ascension to power.

Smoke it, and flavor comes to you in waves: first, a base of tangy citrus…then comes a blanket of dark spices.  Layers of dark chocolate and espresso appear, each adding depth to the rich, thick smoke that pours off this torpedo. Light pepper lurks under the surface, along with oak and cinnamon. By halfway, the blend adds a coating of leather; dried fruit returns, which is then overlapped by coffee and earth.

Throughout, the Serie V Melanio smokes nearly-full – even forceful at times – but remains smooth and creamy, even as the complexity blossoms with each tasty layer. And that complexity immediately brought to mind how Crosby Stills & Nash’s unique harmonies stack so neatly in a stirring, powerful wall of sound.

Why They Pair Well

The “Wooden Ships” story supposedly started with Stills and Crosby jamming together on Crosby’s boat, along with Paul Kantner of Jefferson Airplane (who performed their own version of this song in their Woodstock set, but this just ended up being more famous). It was recorded for the Crosby, Stills & Nash debut album in ’69, leading off on side two of the record.

It’s important to note that it was actually Crosby, Stills, Nash & Young who played Woodstock…Neil Young (a veteran of Buffalo Springfield, with Stephen Stills) joined CSN to help round out their live sound, and their first show together was on August 16, 1969, in Chicago. Neil’s second appearance would be in front of 500,000 people at Woodstock the next night.

Just as Melanio burns with thick, lush layers of flavor, so do Crosby, Stills & Nash’s gorgeously shimmering harmonies…but this beauty is ironic and unfortunate: the words are really describing what it’s like to survive a nuclear holocaust (“Horror grips us as we watch you die”), living on iodine pills (“Say, can I have some of your purple berries?”), men in radiation suits (“Silver people on the shoreline, let us be”) and escaping the apocalypse:

Go, take your sister then, by the hand,

lead her away from this foreign land,

Far away, where we might laugh again,

We are leaving – you don’t need us.

Per the liner notes (vinyl is where it’s at, folks) the band “imagined ourselves as the few survivors, escaping on a boat to create a new civilization.”

The smoke and the song both feature incredible layered sensations; and just as the lyrics talk about leaving devastation behind for a fresh start, think about the Oliva family being forced from their home by the destruction wrought by the Castro regime.

Those are the ties that bind Oliva to CSN for a smoky, 90-minute love-fest…

Track 12

Jared’s Pick:

“Red House” – Jimi Hendrix

Album: Are You Experienced?
Release Year: 1967
Genre: Blues

Cigar Smoked While Listening:

Illusione ONEOFF

Illusione ONEOFF

Size: Canonazo (6 1/8” x 52)
Strength: Medium
Wrapper: Nicaragua
Binder: Nicaragua
Filler: Nicaragua

About The Cigar:

Okay, so let’s address the elephant in the room. Yes, there’s a peace sign on the band. And yes, that certainly ties into the Woodstock theme. I’d be lying if I said it wasn’t the reason for my choice, but we’ll get into that later. In the early 2000s, ONEOFF was a cult cigar that seemed to vanish almost overnight, making the originals extremely hard to find. Having been resurrected by Illusione, the cigars are now made by Aganorsa Leaf and are said to be as good as the original. I never got my hands on one of the earlier blends, so I couldn’t say – but so far, I’m thoroughly enjoying the new brood.

With a proprietary blend of Nicaraguan tobaccos, ONEOFF has a medium-bodied profile that exhibits an emphasis on flavor. In short, it’s smooth, easygoing, and rich – a three-part harmony that seldom exists in a single blend. You may notice notes of cedar, exotic spices, and a trace of cinnamon on the finish. And even though the cigar is a bit on the pricier side, I think it’s still worth the investment. It might not be your everyday smoke, but it’s going to satisfy when you reach for it on special occasions.

Why They Pair Well:

We already got the peace sign out of the way, but there’s more to this pairing than simple aesthetics. For one, they’re both laid back and effortless. The groove in the background of “Red House” is based on 12-bar blues, and there’s something centering about that progression. You close your eyes, nod your head, and you disappear into some other plane of existence for a while. It’s hypnotic. Sprinkled throughout this cut, you’ll hear Jimi’s bold and up-front walking leads. Just like the cigar, it adds a layer of spice, but he also knows when to tone it down and play reserved when needed, too. It’s this quality of the song that reminds me of the cigar. Both are smooth and bold when they need to be. A tasteful cigar with some tasteful licks? I’ll take two.

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Jack Bliesath
4 years ago

Darn good picks!!

Jared Gulick
4 years ago
Reply to  Jack Bliesath

Thanks, Jack!

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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