The late Anna Nicole Smith gained fame by modeling for Guess Jeans and Playboy and bared a striking resemblance to Marilyn Monroe. Anna Nicole was so inspired by the actress that she once told the press, "I want to be the new Marilyn Monroe." She also explained, "I just feel a connection with Marilyn Monroe. I just love her. I just completely feel what she went through." Sadly, both women died of drug overdoses — Marilyn at 36 and Anna Nicole at 39.