Jolie next took the supporting role of a sociopathic Buy Bulk SMS Service mental patient in Girl, Interrupted (1999), an adaptation of Susanna Kaysen's memoir of the same name. While Winona Ryder played the main character in what was hoped to be a comeback for her, the film instead marked Buy Bulk SMS Service Jolie's final breakthrough in Hollywood. She won her third Golden Globe Award, her second Screen Buy Bulk SMS Service Actors Guild Award, and an Academy Award for Best Supporting Actress in 2000. For Variety, Emanuel Levy noted, "Jolie is excellent as the flamboyant, irresponsible girl who turns out to be far more instrumental than the doctors in Susanna's rehabilitation."

In 2000, Jolie appeared in her first summer Buy Bulk SMS Service blockbuster, Gone in 60 Seconds, which became her highest-grossing film to that point, earning $237.2 million internationally. She had a minor role as the mechanic Buy Bulk SMS Service ex-girlfriend of a car thief played by Nicolas Cage; The Washington Buy Bulk SMS Service Post writer Stephen Hunter criticized that "all she does in this movie is stand around, cooling Buy Bulk SMS Service down, modeling those fleshy, pulsating muscle-tubes that nest so provocatively around her teeth." Jolie later explained that the film had been a welcome relief after her emotionally demanding role in Girl, Interrupted.

Although widely praised for her Buy Bulk SMS Service acting and performances, Jolie had rarely found films that appealed to a wide audience, but 2001's Lara Croft: Tomb Raider made her an international superstar. An adaptation of the popular Tomb Raider video games, the film required her Buy Bulk SMS Service to learn an English accent and undergo extensive martial arts training to play the archaeologist-adventurer Lara Croft. Although the film generated mostly negative reviews, Jolie was generally praised for her physical performance; Buy Bulk SMS Service Newsday's John Anderson commented, "Jolie makes the title character a virtual icon of female competence and coolth." The film was an international hit, earning $274.7 million worldwide, and launched her global reputation as a female action star.