16Anna Nicole Smith – 39-Years Old
Anna Nicole Smith was one of the most famous Playmates to ever pose for Playboy. She was named "Playmate of the Month" in May, 1992, though she did appear on the cover earlier in that year in March. While Smith would enjoy a successful modeling career and some
acting here and there, it was her shocking marriage to the 89-year-old oil tycoon, Howard Marshall, that gained her some major notoriety. One year after their marriage, Marshall died, leaving behind a mind-blowing $1.6 billion estate, to which Smith was willed half. Obviously, this didn't sit well with Marshall's family, and there was a lengthy court battle that would extend long after Smith's death in 2007, the result of accidental drug overdose. There were reports that Smith struggled with prescription drugs and even had a mild personality disorder, plus she had great difficulty coping with her son's death the year prior. Smith was 39-years old when she died.