Jolie began working as a fashion model at 14. She was signed with Finesse Model Management and modeled in both the United States and Europe, working mainly in Los Angeles, New York and London. She also appeared in numerous music videos, including those of Meat Loaf (”Rock’n’Roll Dreams Come Through”), Antonello Venditti (”Alta Marea”) and Lenny Kravitz (”Stand by My Woman”). At the age of 16 Jolie returned to theatre, and played her first role as a German dominatrix. She began to learn from her father, as she noticed his method of observing people to become like them. Their relationship during this time was less strained, with Jolie realizing that they were both “drama queens”.
Jolie appeared in five of her brother’s student films, made while he attended the USC School of Cinematic Arts, but her professional movie career began in 1993, when she played her first leading role in the low budget film Cyborg 2, as Casella “Cash” Reese, a near-human robot, designed to seduce her way into a rival manufacturer’s headquarters and then self-detonate. Following several undistinguished projects she starred as Kate “Acid Burn” Libby in her first Hollywood picture, Hackers (1995), where she met her first husband Jonny Lee Miller. The New York Times wrote, “Kate (Angelina Jolie) stands out. That’s because she scowls even more sourly than [her co-stars] and is that rare female hacker who sits intently at her keyboard in a see-through top. Despite her sullen posturing, which is all this role requires, Ms. Jolie has the sweetly cherubic looks of her father, Jon Voight.” The movie failed to make a profit at the box-office, but developed a cult following after its video release.
She appeared as Gina Malacici in the 1996 comedy Love Is All There Is, a modern-day loose adaptation of Romeo and Juliet set among two rival Italian family restaurant owners in Bronx, New York. In the road movie Mojave Moon she was a youngster, named Eleanor Rigby, who falls for Danny Aiello, while he takes a shine to her mother, Anne Archer. Still in 1996 she played Margret “Legs” Sadovsky, one of five teenage girls who form an unlikely bond in the film Foxfire after they beat up a teacher who has sexually harassed them. The Los Angeles Times wrote about Jolie’s performance, “It took a lot of hogwash to develop this character, but Jolie, Jon Voight’s knockout daughter, has the presence to overcome the stereotype. Though the story is narrated by Maddy, Legs is the subject and the catalyst.”
In 1997 Jolie starred with David Duchovny in the thriller Playing God, a film portraying a famed L.A. surgeon who is stripped of his medical license and is lured deep into the criminal world where he meets Jolie’s character, Claire. The movie was not received well by critics and Roger Ebert noted that “Angelina Jolie finds a certain warmth in a kind of role that is usually hard and aggressive; she seems too nice to be [a criminal’s] girlfriend, and maybe she is.” She then appeared in the TV movie True Women, a historical romantic drama set in the West, and based on the book by Janice Woods Windle.