After separating from Billy, Anna Nicole supported herself and her son by dancing topless. Her chosen profession yielded two major milestones in her highly troubled life. The first of which came when a friend told her to send her picture to Playboy. The magazine liked her, and she went on to become Playmate of the Month in May 1992 and Playmate of the Year in 1993.
After her death, Hugh Hefner said, "She was a dear friend who meant a great deal to the Playboy family and to me personally."