In 1995, Bookstaver graduated from the USC School of Cinema-Television. In 1999, he directed the film Scriptfellas.
As a television director, some of Bookstaver's episodic credits include Prison Break, The O.C., Dawson's Creek, One Tree Hill, House, Harper's Island, Jericho, White Collar, Fastlane and Bones.
Bookstaver married actress Rena Sofer in 2003. On August 5, 2005, Bookstaver had his first child with Sofer, named Avalon Leone, in Los Angeles.