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Girl Skateboards' success prompted the unveiling of a sister brand, Chocolate, a year after it was founded, and the team expanded to include new riders and management. In 2013, Howard and Carroll explained that they were inspired to launch the brand when their close friend, professional skateboarder Chico Brenes, was left behind at the airport before they could begin a skateboard tour because he was too tall to fit in the van.
Brenes, Daniel Castillo, Paulo Diaz, Richard Mulder, Shamil Randle, Gabriel Rodriguez, and Ben Sanchez were the original members of the team. A team portrait was showcased in an ad celebrating the team's 15th anniversary that ran in 2009. Anthony Pappalardo and Jesus Fernandez, two riders who were unavailable for the shoot, had their portraits taken separately and included in the ad. In addition to their own work (Las Nueve Vidas De Paco, 1995), The Chocolate Tour, 1999), Se Habla Canuck, 2004, Hot Chocolate, 2004, and A Little Chunk of Chocolate, 2005), the Chocolate crew has appeared in a number of Girl videos (such as Goldfish and Yeah Right!) (2006).
Jerry Hsu was introduced as the new Chocolate skateboard company pro in a video posted on the Crailtap YouTube channel on November 12, 2013. Crailtap is the official channel of the Girl Distribution Company. Performers in the video sketch include Carroll, Marc Johnson, Stevie Perez, Chris Roberts, Elijah Berle, and Gino Ianucci. The skateboarders (minus Ianucci, who shows up at the very end of the skit) meet in a Mexican restaurant to discuss the addition of a professional team member for the Chocolate brand. The members of the group articulate a set of criteria—a set of criteria linked to Hsu's career to this point—and Hsu then appears as the waiter. Elijah Berle, another Chocolate rider, and Hsu both departed the company that year (2017).
In August of 2014, the Art Share Gallery in Los Angeles, California hosted an art show honouring the Chocolate brand on the occasion of its 20th anniversary. During the event, the Berrics website spoke with artist Evan Hecox and Brenes for a feature article.
Chocolate went pro with Yonnie Cruz in the summer of 2017 after the release of "The Flare" video for Lakai Limited Footwear. With the 2019 "T.O.N.Y. Tour" video, Chocolate officially welcomed new amateur members Hakeem Ducksworth, James Capps, and Carl Aikens.
Following the 2021 release of "Bunny Hop," Chocolate made the decision to turn pros James Capps and Carlisle Aikens, recruited Jordan Trahan, and dropped their first long-form video since Pretty Sweet (2012).