#20: Anna Nicole Smith’s Death

by VH1

Playboy model. Senior citizen sex toy. The unholy love child of Marilyn Monroe and the Michelin Man. Anna Nicole Smith was created so the world could marvel at just how messed up one person could get and still not be Britney Spears. Just ask anybody who owns The Anna Nicole Show: The Complete Series on DVD.

The dust seemed to have cleared after the death of Smith’s 20-year-old son Daniel, from an overdose of prescription pills and methodone, and her commitment ceremony to lawyer and long-time pal Howard K. Stern. Then Smith’s lifeless body was found in a Florida hotel room in February 2007. The autopsy showed she had suffered an accidental overdose of prescription medication — none of which had actually been prescribed to her. Then things got really weird.

Stern took custody of Smith’s infant daughter Dannielynn, whose paternity was contested by ex-boyfriend Larry Birkhead. After a court battle and DNA test proving Birkhead was the father, Stern surrendered custody. Then a book alleged that Birkhead and Stern were really lovers. And then our heads exploded. — Charles Bottomley

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Anna Nicole Smith [Photo by Kevin Winter/Getty Images]