Chocolate Skateboards was founded by former Plan B teamriders Rick Howard and Mike Carroll in 1994, the year after the two men had founded their first company, Girl. Chocolate continues to be distributed by the Girl Distribution Company, the California-based company which also distributes Girl Skateboards, Royal Skateboard Trucks, Ruby Republic and Fourstar Clothing.
The original Chocolate team consisted of Keenan Milton, Chico Brenes, Daniel Castillo, Paulo Diaz, Richard Mulder, Shamil Randle, Gabriel Rodriguez and Ben Sanchez, many of whom made guest appearances in early Girl videos such as Goldfish. Over the years, Chocolate has also produced its own videos, such as Las Nueve Vidas de Paco (1995), The Chocolate Tour (1999), Se Habla Canuck (2004), Hot Chocolate (2004) and A Little Chunk of Chocolate (2006).
Brenes and Castillo are still with Chocolate, and make up the current team together with Vincent Alvarez, Kenny Anderson, Elijah Berle, Justin Eldridge, Jesus Fernandez, Gino Iannucci, Marc Johnson, Stevie Perez, Raven Tershy and Chris Roberts. In a video published on Girl’s official YouTube channel Crailtap in November 2013, former Enjoi rider Jerry Hsu was revealed as a new member of the Chocolate team.
2012’s full-length Pretty Sweet, filmed in locations around the globe including Nicaragua, Costa Rica, Panama, China, Barcelona and Berlin, includes parts from the team members of both the Girl and Chocolate brands. Produced by the legendary team of Spike Jonze, Ty Evans, Aaron Meza and Federico Vitetta, it was named best video of the year at the 15th Annual Transworld SKATEboarding Awards event in 2013.