As she grew up, Paltrow's burgeoning beauty and developing acting talent began to win her small film roles, beginning with Shout and Hook in 1991. After a well-received spot opposite her mother in the television mini-series Cruel Doubt (1992), Paltrow decided to abandon her art history studies at the University of California at Santa Barbara to pursue acting full time.
The decision paid off—Paltrow won a string of roles in films like Malice (1993), co-starring Nicole Kidman and Alec Baldwin, Flesh and Bone (1993), and Jefferson in Paris (1995), co-starring Nick Nolte. In 1995, Paltrow appeared in the controversial Seven with Morgan Freeman and Brad Pitt. A romance with the latter helped propel Paltrow into the headlines, just as she began to win starring roles in The Pallbearer (1996), Emma (1996), Great Expectations (1998), and A Perfect Murder (1998) with Michael Douglas. Paltrow confirmed her superstar status with an inspired performance in 1998's Shakespeare in Love, as the immortal Bard's purported muse. The role won her a Best Actress Oscar and made her one of Hollywood's most sought-after female performers.
The willowy blonde also made a name for herself in the gossip columns with much-publicized relationships and break-ups with both Pitt and Ben Affleck, the Oscar-winning co-screenwriter of Good Will Hunting (1997). Affleck also appeared (in a relatively small role) in Shakespeare in Love. He and Paltrow, who broke up amicably in early 1998 after a yearlong romance.
In 1999, Paltrow starred with Matt Damon in director Anthony Minghella's lush production of The Talented Mr. Ripley, a novel by Patricia Highsmith. In 2000, she starred in the karaoke comedy-drama Duets, directed by her father, Bruce Paltrow, and the romantic Bounce, opposite Affleck. In late 2001, Paltrow donned an unflattering fat suit for some of her scenes in the crude comedy Shallow Hal, costarring Jack Black and directed by Peter and Bobby Farrelly. She also joined an all-star cast, including Gene Hackman, Anjelica Huston, Ben Stiller, Bill Murray, Danny Glover, and Luke and Owen Wilson, in The Royal Tenenbaums, directed by Wes Anderson. In 2002, she starred in the literary adaptation Possession, as well as Miramax's romantic spoof A View From the Top.
In October 2002, while vacationing in Italy to celebrate her 30th birthday, Gwyneth's father, Bruce, succumbed to complications from pneumonia after a battle with throat cancer. Following his death, Gwyneth pulled out of some film projects, returning to the screen in the literary drama Sylvia in 2003, about the iconic, tragic poet Sylvia Plath, who killed herself in 1963.