Dr. Bookout received his undergraduate degree in biology and chemistry from the University of Wisconsin in 1989. He attended Wayne State University where he earned his medical degree in 1993. Dr. Bookout completed a general surgery internship and an orthopedic surgical residency. He received specialty training in adult joint reconstruction as a fellow at Hennepin County Medical Center in Minneapolis, Minnesota.

Dr. Bookout also served as a general medical officer in the United States Navy. He is board certified by the American Board of Orthopedic Surgeons and holds hospital privileges at William Beaumont Grosse Pointe; Henry Ford Cottage, Grosse Pointe; St. John Hospital, Detroit; St. John Macomb Hospital Center, Warren; Henry Ford Macomb, Clinton Twp.