A voluptuous bottled-blonde bombshell with a tempestuous and ultimately tragic personal life, this former model was famous for being infamous. After dropping out of high school, Smith found herself married with a kid by the time she turned 18. But a divorce, a gig as a topless dancer and a boob job jump-started her entertainment career. In 1992, a spread in Playboy got her lots of exposure, and by 1993 she was striking sexy, Marilyn-like poses in ads for Guess jeans. The following year, the 26-year-old married longtime fan and octogenarian millionaire J. Howard Marshall II and made her film debut as (what else?) a sexpot in The Hudsucker Proxy. But Smith's seemingly inevitable descent came quickly. After her husband died in 1995, she and his other heirs engaged in a bitter battle over his fortune and she soon filed for bankruptcy. On the professional front, her lack of acting talent, fluctuating frame and perpetually confused demeanor precluded any chance of actually working. But the advent of reality TV gave Smith a second chance at the spotlight, and she launched The Anna Nicole Show in 2002. Featuring an out-of-it Smith and her creepy entourage, including her sleazy lawyer-cum-lover Howard K. Stern, her bizarrely devoted assistant, and her seemingly well-adjusted teenage son Daniel, the series was high camp. While it only lasted two seasons, her misadventures — including a stunning weight loss supposedly achieved via diet aide TrimSpa, and a number of drug-addled public appearances — kept her in the public eye. In September 2006, Smith and Co. were plastered all over the tabloids when Daniel died of a lethal combination of methadone, Zoloft and Lexapro, three days after his mom gave birth to her daughter Dannielynn Hope. Three different men — Smith's photographer ex Larry Birkhead, supposed beau Prince Frederic von Anhalt and Stern — claimed to be the baby's daddy, and a paternity battle ensued. (Although Stern's name was listed on Dannielynn Hope's birth certificate, Birkhead turned out to be her biological father.) While Smith tried to put on a brave public face, the troubled starlet became increasingly fragile and emotional. On February 8, 2007, after being found unconscious in a Florida hotel room, she was rushed to the hospital where she was pronounced DOA. The cause of death was an accidental overdose of multiple prescription drugs. Throughout her life, she had been compared to Marilyn Monroe and like that Hollywood icon, Smith died tragically before the age of 40. Although Smith had long been a pop-culture punch line, her untimely demise was undeniably heartbreaking.