Caswell Berry has been killing it since he made his video debut in Tiltmode’s 2001 video, Man Down, where he became part of a new generation of super consistent kids that could skate transition and street with equal poise. He won the Tampa Am in 2002, turned pro for Toy Machine the same year, but joined the Enjoi squad in 2004 and claimed the opening part in Enjoi’s Bag Of Suck, which contributed to the project winning “Video Of The Year” from TransWorld. Caswell competed in the Maloof Money Cup in 2010 and made the finals, placing 12th overall. He hasn’t been competing much recently as he’s had several big videos to work on including Osiris’ Never Gets Old, Volcom’s True to This, and the latest Enjoi project, Oververt, which featured some classic Berry bangers, including a marathon of a 50-50 that was easily 50 feet long.