Jolie Breakthrough, 1997–2000

Jolie's career prospects began to improve after her performance as Cornelia Wallace in the 1997 biopic George Wallace for which she won a Golden Globe Award and was nominated for an Emmy. The film was highly praised by critics and, among other awards, received the Golden Globe for "Best Miniseries/Motion Picture made for TV". She played the second wife of the segregationist Governor of Alabama who was shot and paralyzed while running for President. The film starred Gary Sinise and was directed by John Frankenheimer.

In 1998, Jolie starred in HBO's Gia, as the supermodel, Gia Carangi. The film depicted a world of sex, drugs and emotional drama, and chronicled the destruction of Carangi's life and career as a result of her drug addiction, and her decline and death from AIDS. Vanessa Vance from Reel.com noted, "Angelina Jolie gained wide recognition for her role as the titular Gia, and it's easy to see why. 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."[20] For the second consecutive year, Jolie won a Golden Globe and was nominated for an Emmy. She also won her first Screen Actors Guild Award. In accordance with Lee Strasberg's method acting Jolie reportedly prefers to stay in character in between scenes during many of her films, and as a result has gained a reputation for being difficult to deal with. While shooting Gia, she told her then-husband Jonny Lee Miller that she wouldn't 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.'"[21]

Following Gia, Jolie moved to New York and stopped acting for a short period of time, because she felt that she had "nothing else to give". She enrolled at New York University to study filmmaking and attended writing classes. She described it as "just good for me to collect myself" on Inside the Actors Studio.[22]

Jolie returned to film as Gloria McNeary in the 1998 gangster movie Hell's Kitchen, and later that year was part of an ensemble cast that included Sean Connery, Gillian Anderson, Ryan Phillippe and Jon Stewart in Playing by Heart. The drama tells the story of several seemingly unconnected characters, with Jolie playing a young club-scene hipster, Joan. The film received predominantly positive reviews and Jolie was praised in particular. The San Francisco Chronicle wrote, "Jolie, working through an overwritten part, is a sensation as the desperate club crawler learning truths about what she's willing to gamble."[23] Jolie won the Breakthrough Performance Award by the National Board of Review.

In 1999, she starred in Mike Newell's comedy-drama Pushing Tin, about two air traffic controllers who engage in macho conflict, co-starring alongside John Cusack, Billy Bob Thornton, and Cate Blanchett. Jolie played Thornton's seductive wife Mary Bell. The film received a lukewarm reception from critics and Jolie's character was particularly criticized. The Washington Post wrote, "Mary (Angelina Jolie), a completely ludicrous writer's creation of a free-spirited woman who weeps over hibiscus plants that die, wears lots of turquoise rings and gets real lonely when Russell spends entire nights away from home."[24] She then worked with Denzel Washington in The Bone Collector, an adapted crime novel written by Jeffery Deaver. Jolie played Amelia Donaghy, a police officer haunted by her cop father's suicide who reluctantly helps Washington track down a serial killer. The movie grossed $151 million worldwide,[2] but was a critical failure; the Detroit Free Press concluded, "Jolie, while always delicious to look at, is simply and woefully miscast."[25]

Jolie next took the supporting role of Lisa Rowe alongside Winona Ryder in Girl, Interrupted (1999), a film that tells the story of mental patient Susanna Kaysen, and which was adapted from Kaysen's original memoir Girl, Interrupted. While the lead role of the film was Ryder's character, and hoped to be a comeback for Ryder, the film instead became the "welcome-to-Hollywood coronation" for Jolie.[26] Jolie won her third Golden Globe, her second Screen Actors Guild Award and an Academy Award for Best Supporting Actress. Variety noted, "Jolie is excellent as the flamboyant, irresponsible girl who turns out to be far more instrumental than the doctors in Susanna's rehabilitation"[27] and Roger Ebert wrote about her performance:

“ Jolie is emerging as one of the great wild spirits of current movies, a loose cannon who somehow has deadly aim.[28] ”

In 2000, Jolie appeared in her first summer blockbuster Gone In 60 Seconds, in which she played Sarah "Sway" Wayland, ex-girlfriend of car-thief Nicolas Cage. The role was small, and the Washington Post criticized that "all she does in this movie is stand around, cooling down, modeling those fleshy, pulsating muscle-tubes that nest so provocatively around her teeth."[29] She later explained that the film was a welcome relief after the heavy role of Lisa Rowe, and it became her highest grossing movie up until then, with $237 million internationally.[2]