Gwyneth Paltrow — 1994

Age: 21

#Fact: Gwyneth is posing here with James Ivory, who was her director on the film Jefferson in Paris. After this photo was taken, Gwyneth and Brad Pitt would soon start their three-year-long relationship after meeting on the set of Se7en. In 1999, Gwyneth won Actress in a Leading Role for Shakespeare in Love.