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., Chicago Fire, Chicago PD, 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, the couple's first child together, Avalon Leone, was born in Los Angeles. Bookstaver and Sofer eventually divorced. In 2019, Sofer announced they had reconciled, and in April she announced their engagement.