After dropping out of high school, Anna Nicole works at Jim's Krispy Chicken Shack, where she meets Billy Smith. At 17, she marries the 16-year-old cook and the pair welcome son Daniel in January 1986. They divorce a little over a year later. "[Billy] was so sweet and so cute back there, cookin' chicken," she reminisces to PEOPLE.
Just four years after making $60 a week as a Wal-Mart checkout girl, the single mom sends nude photos of herself to Playboy, and lands a photo shoot with the magazine. Smith appears on the cover dressed in a blue evening gown with a plunging neckline. In June 1993, Hugh Hefner names the former stripper Playmate of the Year, which leads to renewed attention from a few ex-boyfriends. "They never called before," Smith tells PEOPLE. "I have no desire to see them because every single one of them cheated on me and I caught them."
Months after seeing her in Playboy, Guess president Paul Marciano makes Smith the face of the popular jeans brand. The 5'11", 155-pound, 36DD Smith is a vast departure from previous jobholder, Claudia Schiffer. "She brings back visions of Hollywood glamour," Guess photographer Daniela Federici says to PEOPLE. "We haven't seen that kind of charisma since Marilyn Monroe."
In front of 11 attendees at Houston's White Dove wedding chapel, Smith marries 89-year-old oil billionaire J. Howard Marshall II. Smith met the twice-divorced and wheelchair-bound Marshall while working as a topless dancer at the Houston strip club Rick's in 1988.
Following months of illness, Marshall dies of pneumonia. In a prelude to what becomes a long battle over his assets, Smith and Marshall's eldest son, E. Pierce, 56, plan separate memorial services. Smith's is a 25-minute celebration in which 30 attendees (most of whom were acquainted with Marshall through Smith) are treated to melon balls. The service also features teddy bears draped around the casket and a banner reading "From Your Lady Love" in gold glitter. The second ceremony – a solemn two-hour affair at the same funeral home – is attended by most of Marshall's family, including his first wife, Eleanor.
After having her $50,000 monthly allowance severed and losing the title to the million-dollar Texas ranch where she was living shortly after Marshall's death, Smith begins a long legal battle in L.A. bankruptcy court against her late husband's son, E. Pierce Marshall. She fights to claim at least $500 million of Marshall's estate. By January 2005, she has won her case twice but lost her money on appeals.
The premiere of Smith's E! Network reality series, The Anna Nicole Show, draws in 4 million households and features Smith, her son Daniel, assistant Kim Walther and lawyer Howard K. Stern. The former model slurs observations about subjects like Palestinian suicide bombers ("Don't they think it was kinda painful?"), refers to her breasts as "my puppies" and whimpers as she places her husband's urn on top of the television set. Watching the debut at a private party while she chows down on deep-fried pickles, barbecued ribs, bubble gum and Budweiser, Smith remarks, "I look stoned out of my mind!"
Named spokeswoman for the diet supplement Trimspa, Smith announces on her own E! special that she shed 69 lbs. using the over-the-counter drug. The product isn't without controversy: Two class-action lawsuits are filed in the same month accusing the manufacturers of misrepresenting the ingredients and effects of Trimspa. In February 2007, just two days before her death, another class-action lawsuit is filed against the company and Smith.
Introducing performer Kanye West at the American Music Awards in L.A., Smith garbles her words, fondles her breasts and asks the audience "Do you like my body?" before being helped offstage. Host Jimmy Kimmel jokes to the crowd, "I told her to stay away from Snoop Dogg's brownies."
Smith's chaotic legal battle over of her late husband's estate with his son E. Pierce goes to the Supreme Court. The nine justices unanimously rule that Smith has the right to pursue her suit in federal court. Marshall's son, E. Pierce, dies from an infection six weeks later, but the case is still pending.
BIOGRAPHY (top to bottom): Splash News; Scott Downie/Celebrity Photo; Jeffrey Lowe; Splash News; Carlos Rios/AP; Stewart Volland/E! Entertainment; Mark J. Terrill/AP