While watching her mother, Blythe Danner, perform at the Williamstown Theatre Festival in Massachusetts, 2-year-old Paltrow is thrust onstage and surprises everyone by reciting her mother's lines. "She could barely talk," Danner later tells Time, "yet she knew the whole speech better than I did. We should have known then, I guess."
Without much experience, 18-year-old Paltrow appears alongside her mother in Picnic at the Williamstown Theater Festival. Her father, television director Bruce Paltrow, is sufficiently impressed with his daughter's performance to encourage her to abandon university studies for acting. Previously, her parents said she should stay in school.
In her first television role, Paltrow appears in the NBC miniseries Cruel Doubt alongside her mother. Her more considerable acting background notwithstanding, Danner tells PEOPLE, "She got the part first, and I guess they thought I looked right as her mother.'' The following year, Paltrow takes a small part in the psychological drama Flesh and Bone, but her performance makes her a young actress to watch. The National Society of Film Critics nominates her for Best Supporting Actress for the role.
Paltrow begins dating Se7en costar Brad Pitt, PEOPLE's Sexiest Man Alive, catapulting Paltrow into the headlines. "Our first date was at an Italian restaurant in L.A., and no one gave us a glance," Paltrow tells You magazine. "Now it's a case of 'Who's that girl?'" In April, while in St. Barts, a paparazzo captures the couple sunbathing nude, which leads to an invasion-of-privacy lawsuit that Pitt wins.
After a year together, Pitt gushes as he accepts the Golden Globe for Best Supporting Actor in 12 Monkeys, calling Paltrow "the love o' my life, my angel." Equally smitten, Paltrow tells London's You magazine, "I am properly in love for the first time in my life, and I do not care if my former boyfriends read this." That August, PEOPLE names Paltrow one of the Hottest 30 Stars Under 30 and one of the 25 Most Intriguing, calling her "the face that launched a thousand magazine covers."
After starring as a matchmaker in Jane Austen's Emma, Paltrow, 25, accepts Pitt's proposal to marry while in Mendoza, Argentina. But the engagement is short-lived. Just seven months later, on June 16, 1997, Pitt's publicist announces the couple has broken up.
Paltrow goes alone to a deserted island in the Caribbean for three days and writes of her adventure for Marie Claire. The actress brings rice, a Swiss Army knife, matches, fish hooks and a hammock. She walks around mostly nude during the day and writes about her seclusion: "I have learned that I am stronger than I thought. I am braver than I thought."
Paltrow is seen with actor Ben Affleck. The two keep it friendly at first, but two months later are very obviously a romantic item. While at a press junket promoting her film Sliding Doors, the pair kiss for nearly three minutes. The following year though they break up, but are seen together again for a short time in 2000.
After being named on of PEOPLE's 50 Most Beautiful, Paltrow wins an Oscar for her performance as Lady Viola in Shakespeare in Love. In a pink satin Ralph Lauren gown, Paltrow sobs as she accepts the award and thanks her parents: "I would not have been able to play this role, had I not understood love of a tremendous magnitude, and for that I thank my family."
BIOGRAPHY (top to bottom): Ron Galella/WireImage; NBC/Everett; DAVE ALLOCCA/DMIPHOTO; Evan Agostini/Getty; Kevin Mazur; REX USA