Craig was born and grew up in Palo Alto, CA. After graduating and receiving a BFA degree in illustration from Academy of Art University in 1976, Craig spent seven years as a freelance commercial illustrator. He landed a full-time staff illustrator position for Krames Communication, a medical information publishing company. In 1986 he was invited by Barbara Bradley, the Director of the Illustration Department, to teach head drawing and various illustration courses. He worked part time for eleven years while continuing his freelance work. In 1997 he moved to Burbank, CA and taught drawing classes for Walt Disney Feature Animation, Associates in Art under Mark Westermoe, and Woodbury University while continuing his teaching at the Academy. He returned to San Francisco in 1999 and was asked to lead the Foundations Department at the Academy for a semester. Since 2000 he has taught Heads and Hands full-time exclusively for the School of Illustration and currently teaches Heads and Hands full-time for the School of Fine Art.