It was the October 1971 issue of Playboy Magazine when the first black woman, the beautiful Darine Stern graced the cover by herself. Even though she made the cover however, she was never a Playmate.
Darine’s cover went on to later inspire the November 2009 issue of Playboy that featured Marge Simpson of the famous cartoon show, The Simpsons. Unfortunately, there is not too much information about Darine. It is known that she became a high-profile model for Ford Models. She died at the age of forty-seven from complications of breast cancer.
Jennifer Jackson, an 18-year-old college student walked into the Chicago headquarters of Playboy looking for secretarial work. Right away she was hired but as a Playmate. She was immediately issued one of the well-known bunny costumes. She was the youngest hire at that location who later became the first black Playmate in the March 1965 issue six years prior to Darine being on the cover. Since this came around during the time of the Civil Rights Movement, many saw Jennifer’s debut as breaking racial barriers, which did not dawn on her then. Being from Chicago, Jennifer said it was typical to see black professionals such as doctors, dentists and businessmen in her neighborhood.
For many years she felt ashamed for taking the nude photos. She thought she wouldn’t be able to get work when others discovered her Playboy background. It wasn’t until after she attended the Playmate reunion in 1999, Jennifer stated she no longer felt shameful for her photos in the popular magazine. After her time with Playboy, she became a model for Ford Modeling Agency. She was also the first black model to do ads and print work for Lady Clairol and KOOL cigarettes. All of these ads went into Ebony Magazine. Jennifer was the poster girl for the Ebony Fashion show.
After a failed marriage and two children, she left her husband, remarried and had her third child. She later went back to school, earned her degree in human services with an emphasis in counseling which allowed her to became an investigator for Child Protective Services in Seattle. After twenty years in that industry, she retired in June 2009.
There were many other beautiful black women who were bunnies and/or graced the cover of the popular adult magazine. These women came from a variety of backgrounds and some went on to further their careers in acting and other creative outlets. Check out the history of black Playboy bunnies and Playmates here: https://www.complex.com/pop-culture/2013/02/a-history-of-black-playboy-playmates/
Special Announcement: My mother was NOT a bunny however she did work at the Playboy Club in Chicago and has plenty of good stories to tell from her time there.