Woolfolk is a graduate of the University of California Berkeley, where he received bachelor"s degrees in Ethnic Studies and Rhetoric. He later graduated from Columbia University, where he received a Master of Fine Arts degree in Film with an emphasis on directing.
He shot his first feature film The Harimaya Bridge in Kōchi Prefecture, Japan and San Francisco. The film had a nationwide theatrical release in Japan in the summer of 2009, and had a limited independent release in the United States in 2010. His play Bronzeville, which he co-wrote, opened to critical acclaim in 2009 and has since enjoyed two successful revivals.
Woolfolk was the recipient of an American Broadcasting Company Entertainment Talent Development Grant, and was later a Walt Disney Studios/American Broadcasting Company Entertainment Writing Fellow.
Woolfolk is a veteran of the Japan Exchange and Teaching Programme (Joint European Torus). He taught junior high school English in Kōchi Prefecture, Japan.
Woolfolk has a deep background in music, having played violin for several years. He also played viola, piano, and flute.
Foreign his first film, the short Rage!, Woolfolk won a Directors Guild of America award. His short films Eki and Kuroi Hitsuji—both shot in rural Japan—won several awards, screened in international film festivals, and played on cable television Woolfolk"s short film, Nico"s Sampaguita—centered around San Francisco"s Fillmore Jazz District—also won a number of awards and screened in several film festivals. Woolfolk"s feature directorial debut, The Harimaya Bridge, which starred Danny Glover, Ben Guillory, Saki Takaoka and Misa Shimizu, won a number of awards, including Best First Time Feature Director at the Pan African Film Festival. The San Francisco Examiner named it "one of the best films of the year," while The Los Angeles Times called it "powerful" and "a unique, complex, consciousness-raising accomplishment." The film was invited to screen at the Smithsonian Institution in Washington, District of Columbia. Woolfolk and Toyama received a nomination for an Ovation Award in the category Best Playwriting for an Original Play.
As a teenager he was a member of Berkeley Youth Orchestra and Young People"s Symphony Orchestra. As a student at the University of California Berkeley he was a member of the University Symphony.
