What Is Jolly Jack-O in VeeFriends and Why Collectors Love It

Every collector community has that one character who takes on a life of their own. In the VeeFriends universe, that character is Jolly Jack-O, a grinning pumpkin who has become the unofficial face of the brand’s fall season.

What started as one of Gary Vaynerchuk’s hand-drawn NFT characters has turned into something much bigger: a growing community, a social movement, and even a coffee shop collaboration.

Jolly Jack-O represents the fun side of collecting, the part that brings people together.

The Origins of Jolly Jack-O

VeeFriends launched in 2021 as Gary Vaynerchuk’s vision for a character-driven universe built on positivity, creativity, and connection.

Every character in the project was drawn by Gary himself, each representing a specific trait or mindset.

Jolly Jack-O was one of the first that stood out. His pumpkin grin and Halloween theme gave him instant charm, but it was his message of joy, warmth, and play that resonated most. He represented the idea that success and fun can coexist, that ambition doesn’t have to cancel out laughter.

Over time, he became a seasonal mascot for the brand, showing up in events, merch, and creative partnerships that celebrate community.

From NFT to Real-World Icon

In 2024, Jolly Jack-O made the jump from digital art to real-world recognition when VeeFriends partnered with Funko to release a limited Jolly Jack-O POP! Vinyl. Only 1,000 figures were produced and sold at New York Comic Con, where Gary Vee appeared at the booth, signed figures, and met fans.

Attendees described the atmosphere as less about hype and more about shared excitement. People waited in line not just for a collectible but for the chance to connect with the community that had formed around VeeFriends. Gary himself spent hours handing out stickers and chatting with fans, making it clear that these characters were about people first.

The following year, the collaboration continued with Gold and Silver Jolly Jack-O POP! variants released at NYCC 2025.

A Character That Builds Community

What makes Jolly Jack-O stand out isn’t scarcity alone, but everything he represents. He’s fun, recognizable, and built around the kind of positivity that keeps the VeeFriends community connected.

At events like New York Comic Con, fans don’t just show up for collectibles. They come to share the experience. When Jolly Jack-O figures first appeared, collectors traded stories, swapped photos, and helped each other track them down. It wasn’t about competition. It was about being part of the moment.

Every fall, that spirit returns. Jolly Jack-O brings people together through art, nostalgia, and the shared excitement of collecting something meaningful. 

He’s a reminder that the best part of this hobby isn’t what you own. It’s the people you meet along the way.

From POP! to Coffee Cups

Jolly Jack-O’s influence has expanded beyond POP! collectibles.

In 2023, VeeFriends partnered with Gregory’s Coffee to release a seasonal drink called the Jolly Jack-O Pumpkin Chai Latte, inspired by the character. 

For fans, it became a small but memorable symbol of what VeeFriends stands for: meaningful, character-driven storytelling that connects people in simple ways.

Why People Love Jolly Jack-O

People love Jolly Jack-O because he captures everything that makes Halloween fun.

He is cheerful, festive, and just spooky enough to fit the season. His wide grin, bright orange face, and playful energy make him easy to like.

Jolly Jack-O has quickly become a fan favorite, not just for what he represents, but for what he might become. His collaborations, from the limited Funko POP! releases to a seasonal pumpkin chai latte with Gregory’s Coffee,  show how VeeFriends is bringing its characters into the real world in creative ways.

Jolly Jack-O has become a fall favorite because he captures the best parts of collecting. People look forward to seeing him return each October, the same way they look forward to pulling out their favorite cards, sorting their binders, and setting up displays for the season.

At Goat Armor, we love that part of the hobby too. Our binders are built to protect the cards that mean something to you, from your newest pulls to the ones that have been with you for years. Wide seams, clear pages, and sturdy covers make it easy to keep your collection safe while still showing it off.