Following a supporting role in the independent film Without Evidence (1995), she starred in her first Hollywood picture, Hackers (1995).The New York Times critic Janet Maslin wrote, "Kate stands out.
Jolie then decided she wanted to act and enrolled at the Lee Strasberg Theatre Institute, where she trained for two years and appeared in several stage productions.
Jolie portrayed Wallace's second wife, Cornelia, a performance Lee Winfrey of The Philadelphia Inquirer considered a highlight of the film.
George Wallace was very well received by critics and won, among other awards, the Golden Globe Award for Best Miniseries or Television Film.
Jolie is fierce in her portrayal—filling the part with nerve, charm, and desperation—and her role in this film is quite possibly the most beautiful train wreck ever filmed." For the second consecutive year, Jolie won a Golden Globe Award and was nominated for an Emmy Award. In accordance with Lee Strasberg's method acting, Jolie preferred to stay in character in between scenes during many of her early films, and as a result had gained a reputation for being difficult to deal with.
While shooting Gia, she told her husband, Jonny Lee Miller, that she would not be able to phone him: "I'd tell him: 'I'm alone; I'm dying; I'm gay; I'm not going to see you for weeks.'" Following the previously filmed gangster film Hell's Kitchen (1998), Jolie returned to the screen in Playing by Heart (1998), part of an ensemble cast that included Sean Connery, Gillian Anderson, and Ryan Phillippe.