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Sebastian Shepherd is the son of a minister and a schoolteacher. Engaged in his church's choir and drama group, he developed a passion for performing early on and began writing screenplays and stories at the age of seven. His earliest works were credited under his birth name, David Jonathan Grant, while some were attributed to a nickname he earned as a beloved camp counselor, "Sheepdog."
At Kent State University, where he earned a bachelor's degree in theater with a minor in English, Sebastian expanded his knowledge of literature, writing, and stagecraft. He acted in various student-directed projects and mainstage productions, portraying roles such as a lovesick Duke in "The Lady from Maxim's" and the Ghost in "Hamlet." During his junior and senior years, he wrote, produced, starred in, and edited the opening credits of his first independent feature film, "Toaster."
On April 1, 2011, Sebastian founded Wolf In Wool Productions and the rap group Chalkskin. Their debut album, "Fresh Donuts," marked the official launch of the company and received praise. Subsequent albums, "Pay Day" (2012) and "The Whitey Album" (2017), gained even greater recognition within the local community. Chalkskin has performed on "1137 Lounge Live," at LA's House of Blues, and at the San Diego Comic Con Nerdcore Show at The Ruby Room, sharing the stage with notable nerdcore artists like MC Lars and MC Frontalot. Wolf In Wool Productions also produces "The Sheepdog Show," a sketch comedy and chat show; "Chalkskin 10," an interview series featuring guests such as William Daniels ("Boy Meets World," "1776") and George R.R. Martin ("Game of Thrones"); along with several other web-based projects.
Sebastian Shepherd is also an author, with a series of books including "Home Street" and "Sick Day.
