Anna Nicole Smith, 39 Years Old
The former 1993 Playmate of the Year modeled for H&M, Guess, Heatherette, and Lane Bryant. She had a highly publicized second marriage to an 88-year-old billionaire, J. Howard Marshall. People suspected she'd married him for his money, which she denied. She died in 2007 as a result of a prescription drug overdose. She'd been battling a press barrage regarding the sudden death of her son, Daniel, and a custody battle over her newborn daughter.