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His feature film directorial work consists of comedies such as Kicking and Screaming, starring Will Ferrell and Robert Duvall, and American Wedding.

Other feature-length projects include the documentary Crips and Bloods: Made in America, which explores the culture of gangs and systemic violence in South Los Angeles.

He produced the film for director Stacy Peralta who premiered it at the 2008 Sundance Film Festival.

Dylan also produced and directed an original television series, “ CONversations with Ricky Jay ,” which was built around sleight of hand artist Ricky Jay.