
Jolie's career prospects began to improve after she won a Golden Globe Award for her performance in TNT's George Wallace (1997). She portrayed Cornelia Wallace, the second wife of Alabama Governor George Wallace, played by Gary Sinise. The film was very well-received by critics and won, among other awards, the Golden Globe Award for Best Miniseries or Television Film. Jolie also received an Emmy Award nomination for her performance.
In 1998, Jolie starred in HBO's Gia, portraying supermodel Gia Carangi. The film chronicled the destruction of Carangi's life and career as a result of her addiction to heroin, and her decline and death from AIDS in the mid-1980s. 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." For the second consecutive year, Jolie won a Golden Globe Award and was nominated for an Emmy Award. She also won her first Screen Actors Guild 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 then-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.'"After Gia wrapped in 1997, Jolie announced that she had given up acting for good, because she felt that she had "nothing else to give." She separated from Miller and moved to New York, where she enrolled at New York University to study filmmaking and attend writing classes; she later described it as "just good for me to collect myself." by her Golden Globe Award win for George Wallace and the positive critical reception of Gia, she resumed her career.
Jolie returned to film in the 1998 gangster movie Hell's Kitchen. Later that year, she appeared in Playing by Heart, part of an ensemble cast that included Sean Connery, Gillian Anderson, Ryan Phillippe, and Jon Stewart. 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." Jolie won the Breakthrough Performance Award from the National Board of Review of Motion Pictures.
In 1999, she starred in the comedy-drama Pushing Tin, alongside John Cusack, Billy Bob Thornton, and Cate Blanchett. The film received a mixed reception from critics, and Jolie's character—Thornton's seductive wife—was particularly criticized. The Washington Post wrote, "Mary (Angelina Jolie) [is] 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." She then co-starred with Denzel Washington in The Bone Collector (1999), an adaptation of a crime novel by Jeffery Deaver. Jolie played 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, but was a critical failure. The Detroit Free Press concluded, "Jolie, while always delicious to look at, is simply and woefully miscast."
"Jolie is emerging as one of the great wild spirits of current movies, a loose cannon who somehow has deadly aim."
—Roger Ebert on Jolie's performance in Girl, Interrupted (1999)
Jolie next took the supporting role of the sociopathic Lisa Rowe in Girl, Interrupted (1999), an adaptation of former mental patient 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 Jolie's final breakthrough in Hollywood. She won her third Golden Globe Award, 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".
In 2000, Jolie appeared in her first summer blockbuster, Gone In 60 Seconds, in which she played Sarah "Sway" Wayland, the 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." later explained that the film had been a welcome relief after the emotionally heavy role of Lisa Rowe. It became her highest grossing movie up until then, earning $237 million internationally











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