Craighead was born in Cleburne, Texas and began his portrait career as a teenager. He grew up in Fort Worth and attended the University of Texas at Austin. He then furthered his art education by attending the National Academy of Design in New York, the Cape School of Art in Massachusetts, and the studio of portrait painter Cedric Egeli in Annapolis.
Craighead maintains an active schedule painting portraits of children, families, and leaders in the corporate, educational, political, and business worlds. His portrait of Senator and former Governor Tim Kaine hangs in the Virginia State Capitol building. He also painted the official portrait of former Virginia governor James Gilmore. His portraits are included in numerous collections throughout the United States and Great Britain.
Reproductions of his portraits have been seen in the The Artist’s Magazine, American Artist magazine, and International Artist magazine. His works have won awards at successive Portrait Society of America competitions. Craighead has a studio in old town Manassas, Virginia.