Chocolate Skateboards: Style, Technique, and Skateboarding Culture from the 90s to Today

Chocolate Skateboards is one of the most iconic, stylish, and respected brands in the history of global skateboarding. Founded in the early 90s as part of the legendary Crailtap family, Chocolate has represented a different vision of street skating from the very beginning: more creative, more fluid, more technical, and deeply rooted in authentic skateboarding culture.

We’re talking about a brand that didn’t just produce skateboards, but directly helped define the style of modern skateboarding through legendary teams, historic videos, iconic graphics, and one of the most recognizable artistic identities in the entire skate scene.

Even today, Chocolate Skateboards continues to be considered one of the most important and influential brands in the global skateboarding world thanks to a unique combination of style, authenticity, and technical innovation.

The Origins of Chocolate Skateboards and the Birth of the Crailtap Family

The history of Chocolate Skateboards has its roots in the early ’90s, during one of the most significant eras in the history of modern street skating. In those years, the skateboarding world was undergoing a massive technical revolution: big pants, small wheels, ledge skating, and switch tricks were completely changing the language of street skating.

It was within this context that the Chocolate project was born.

Originally, the brand was supposed to be called “Sister,” but the name was registered by World Industries before the project could officially take shape. It was precisely from this episode that one of the most important companies in Crailtap’s history began to take form.

Rick Howard and Mike Carroll decided to create a second brand parallel to Girl Skateboards to give a platform to incredible riders who would otherwise have been left without sponsors and without a real place to express themselves.

Thus, Chocolate Skateboards was born.

The first team was simply mind-blowing for its time: Keenan Milton, Chico Brenes, Daniel Castillo, Paulo Diaz, Richard Mulder, Shamil Randle, Gabriel Rodriguez, and Ben Sanchez perfectly embodied the new generation of technical street skating in the 1990s.

These riders skated legendary spots like Embarcadero in San Francisco and contributed enormously to the evolution of modern skateboarding thanks to a technical, creative, and incredibly fluid style.

Chocolate Skateboards and the style that changed street skating

From the very beginning, Chocolate immediately set itself apart from every other skateboarding brand on the market.

The brand’s identity was more artistic, more laid-back, and deeply tied to the riders’ personal style. Chocolate skateboarding wasn’t built solely on big tricks or massive spots, but above all on flow, style, control, and creativity.

And it is precisely this approach that has made Chocolate one of the most beloved brands among skaters worldwide.

The brand quickly began to grow internationally, and the first Chocolate boards became instantly highly sought-after, thanks in part to the extraordinary work of artist Evan Hecox.

Evan Hecox and the Legendary Chocolate Graphics

One of the elements that has made Chocolate Skateboards so iconic over time is undoubtedly the artistic work of Evan Hecox.

A Colorado-born artist, Hecox created one of the strongest visual identities in the history of skateboarding. His minimalist, geometric, and instantly recognizable style contributed enormously to the brand’s global success.

The famous “Chocolate Chunk” logo has become, over the years, one of the absolute symbols of global skateboarding. Even today, many skaters consider Chocolate’s graphics among the most beautiful ever created in skate culture.

Hecox’s artistic approach allowed the brand to build an aesthetic completely different from many other 90s companies, creating a perfect fusion of skateboarding, contemporary art, and urban culture.

Chocolate Videos and the Brand’s Growth

Between the mid-90s and early 2000s, Chocolate Skateboards definitively cemented its position as one of the strongest brands in global skateboarding thanks to a series of skate videos that have become legendary.

Videos like “Las Nueve Vidas de Paco” and “The Chocolate Tour” clearly showcase the technical evolution of the team and street skating during that era.

With the arrival of the new millennium, the bar was raised even higher.

In 2004, “Hot Chocolate” was released, arguably one of the most important videos in the brand’s history. Directed by Spike Jonze and Ty Evans, the video showcased stylish, technical, and incredibly creative skateboarding that immediately became an absolute benchmark for a new generation of riders.

In 2006, “A Little Chunk of Chocolate” was released, while in 2012 the brand appeared in the historic “Pretty Sweet,” the legendary Crailtap video that brought together Girl and Chocolate in one of the most important projects in modern skateboarding.

Chocolate Skateboards in the New Millennium

Over the years, Chocolate has continued to evolve without losing its original identity.

The team is constantly renewing itself by introducing riders who are increasingly technical and stylish. Names like Kenny Anderson, Gino Iannucci, Justin Eldridge, Stevie Perez, Vincent Alvarez, Jesus Fernandez, Raven Tershy, James Capps, and Carl Aikens help keep the brand at the top of the global scene.

Every Chocolate rider possesses a highly personal style, and this has always been one of the most important aspects of the brand’s philosophy.

Jesus Fernandez is known for his impressive power and control, Raven Tershy brings a brutal and lightning-fast style of skateboarding, while riders like Vincent Alvarez and Kenny Anderson perfectly embody the technical and creative flow typical of Chocolate culture.

Meanwhile, the brand continues to develop skateboards of the highest quality using modern construction methods, advanced technologies, and increasingly high-performance materials.

In addition to decks, Chocolate also produces apparel, accessories, griptape, and streetwear collections, always maintaining its strong original artistic identity.

Chocolate Skateboards Today

Even today, Chocolate Skateboards remains one of the most respected and credible brands in the entire global skateboarding scene.

Very few brands can boast such a long history while simultaneously maintaining authenticity, style, and cultural relevance. Chocolate has managed to span several generations of skateboarding without ever losing its original DNA.

The brand continues to represent stylish, creative, and deeply street-oriented skateboarding, keeping alive that authentic connection to the skate culture born in the 90s.

Chocolate boards are still among the most skated and beloved in the world today thanks to their build quality, legendary graphics, and a reputation built over more than thirty years of real skateboarding.

Chocolate Skateboards and Pleasures Milano 

At Pleasures Milano, we select only brands that have truly shaped the history of global skateboarding, and Chocolate Skateboards is undoubtedly one of the most important brands ever to emerge from the American street scene.

We’re talking about a company that has redefined the concept of style in modern skateboarding through legendary riders, historic videos, and an artistic direction that has become iconic for entire generations of skaters.

From the first boards of the ’90s to the current Crailtap team, Chocolate continues to represent authentic, technical, and incredibly stylish skateboarding.

At Pleasures Milano, you’ll find a selection curated by those who have lived and breathed skateboard culture every day for over twenty-five years, choosing only brands that continue to truly influence the global scene.