The Best Halloween Cigars? Crowned Heads & Matt Booth Take over My Cigar Pack's October Selection. | My Cigar Pack

The Month That Just Felt Right

October always hits different.

There is something about the shift in the air, the slower nights, the longer smokes, and the natural pull toward darker themes that makes October one of our favorite months to curate. This year, it landed exactly where we wanted it to.

From the first light-up, this pack feels intentional. Familiar, but still surprising. Comfortable, but not safe. October 2021 is one of those moments where timing, relationships, and creativity all line up at once.

This was not a random collection of cigars. This was a takeover.

Why This October Was Special From the Start

Right out of the gate, we knew this month needed to be different.

October is one of the few times of year where we allow ourselves to lean fully into a theme without forcing it. Halloween does not need explaining in cigar culture. Darker imagery, bolder personalities, limited projects, and a little bit of mystery all feel natural this time of year.

What made this October unique is that it was not just a themed pack. It was a collaborative takeover.

For the first time, we brought together Crowned Heads and Matt Booth in the same pack. Two voices. Two aesthetics. Two philosophies that are very different, but oddly complementary.

John and Matt are longtime friends. Their creative paths have crossed for years, but this was the first time we were able to bring that relationship directly into a My Cigar Pack experience.

That matters.

Working With People, Not Just Brands

This month did not come together overnight.

Projects like this take time. Conversations. Back and forth. Trust. We work on things until they feel right, not until they are convenient. That is especially true when prototypes are involved.

The two Matt Booth blends featured this month are prototypes of something still in development. They are not final releases. They are not hype-driven concepts. They are early looks into what is coming in 2022.

Think of this as a sneak peek. A peekaboo moment. A chance to taste something before it becomes a finished product.

We made the decision to include them because we believe our community understands the value of that process. This was never about perfection. It was about participation.

Crowned Heads, Bias Included

Let’s be honest.

We are Crowned Heads people.

That bias is not hidden here, and it does not need to be. Crowned Heads has been a consistent presence in our packs for a reason. Their cigars fit our philosophy. Their approach to blending, branding, and storytelling aligns naturally with how we curate.

This October selection features some of our personal favorite Crowned Heads cigars. Not because they are new. Not because they are flashy. But because they work.

They are cigars you reach for when you want something reliable without being boring. Cigars that feel just as appropriate on a quiet night as they do in a group setting.

Having Crowned Heads anchor this month gave us a strong foundation. Everything else was built around that.

Matt Booth Prototypes and the Long Game

Matt Booth is one of the most polarizing figures in the cigar industry. That is not a criticism. That is part of what makes his work interesting.

His projects tend to spark conversation. Sometimes disagreement. Always engagement.

The two blends included this month are prototypes. They represent ideas that are still being shaped. We have been working on these with Matt for a while, and October felt like the right moment to let people in early.

This is not a marketing stunt. It is transparency.

We want people to experience the evolution of a project, not just the final product. That is part of what makes cigar culture compelling. Nothing exists in isolation. Every cigar has a backstory, whether it is told or not.

This month, the backstory is part of the experience.

A First-Time Collaborative Takeover

This October marks the first time we have done a true collaborative takeover.

Not a feature. Not a one-off. A full moment where multiple creators come together intentionally for a single release.

John and Matt working together in a pack was not something we took lightly. These are two strong creative voices. Bringing them together required alignment, not compromise.

The result feels cohesive without feeling forced. That balance is difficult to achieve, and we are proud of how it came together.

This is a preview of what is possible when relationships drive curation instead of calendars.

Skull Calaveras and Letting People Play

October is also about fun.

Alongside the cigars, we introduced the Skull Calaveras design. A hybrid visual concept that blends Matt Booth’s skull imagery with the Calaveras identity from Crowned Heads.

Half Matt. Half Crowned Heads. One shared symbol.

Instead of treating it as a static design, we turned it into a challenge. Every order included a temporary tattoo, and we invited everyone to participate in the Skull Calaveras Challenge.

The rules were simple. Be creative. Take a picture. Engage.

We wanted to see how people interacted with the idea. Tattoos on arms, necks, wherever people felt comfortable. Temporary tattoos were included, but permanent ones were jokingly encouraged too.

The goal was not virality. It was connection.

This challenge gave people a reason to engage beyond smoking. It opened up conversations, comments, and shared experiences across platforms.

That is the kind of community energy we want to build.

More Than Just Cigars in a Box

This October pack reinforces something we believe deeply.

A cigar pack should not feel transactional.

It should feel like an invitation. An invitation to try something new, to revisit something familiar, and to be part of a larger conversation. This month did that on multiple levels.

Cigars. Prototypes. Design. Social engagement. Collaboration.

Everything pointed back to the same idea. Cigar culture is better when it is shared.

Supporting the Bigger Picture

As always, we want to be clear about one thing.

We encourage you to support your local brick-and-mortar retailers. They are the backbone of this industry. They are the places where conversations happen, where new smokers are welcomed, and where cigar culture actually lives.

Our goal is not to replace that experience. It is to complement it.

If you find something in this pack that you love, we hope you seek it out locally. If you buy online, Cigar Yard is always there. But the heart of this industry lives in lounges and shops.

That has not changed.

Gratitude and What Comes Next

This October would not have been possible without trust.

Trust from Matt. Trust from John. Trust from everyone involved behind the scenes. And trust from our community to engage with something that is still evolving.

We are grateful for that.

This month is a glimpse into what is coming. Not just in 2022, but in how we approach collaboration moving forward. Slower. More intentional. More connected.

October was about fun, yes. But it was also about laying groundwork.

Final Thoughts

This was not just a Halloween pack.

It was a statement.

A statement about collaboration over competition. About process over polish. About community over consumption.

If you enjoyed this month, tell us. Comment. Email. DM. Call. We are here for that.

And if you did not enjoy something, tell us that too. That feedback is how projects like this get better.

October belongs to Crowned Heads and Matt Booth. But more importantly, it belongs to everyone who smoked along with us.

Thank you for being part of it.