Penny James (born 1942) is an artist and musician and former model. She has appeared on the cover of Playboy magazine five times. (See List of people in Playboy 1960–1969) In October 1965, July 1966, October 1966, March 1969 and August 1969. James was raised in Colorado where, at the age of 20, she was crowned Miss Colorado USA. After being discovered by a scout and acting in several television commercials, James moved to Chicago where she was photographed by Victor Skrebneski. This was when her image started to appear on various newspapers and magazines, including Playboy.