Anna Nicole: The Cover Girl

Take a look back at Smith's iconic Playboy covers and the Guess ads that launched her career

GUESS: 1992

After her appearance on Playboy's cover, the then-25-year-old Smith was signed as a spokesmodel by Guess jeans CEO Paul Marciano. "I didn't know what Guess jeans were," she says. "I just shopped at Wal-Mart and Kmart and stuff like that." Her substantial Guess earnings enabled Smith to hire a nanny to help care for then-7-year-old-son Daniel and buy a four-bedroom home in Houston, three horses and two cars, PEOPLE reported at the time.