Angelina Jolie - Gone In 60 Seconds

Angelina Jolie appeared in her 1st summer blockbuster, Gone In 60 Seconds In 2000, in which Jolie 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."

Angelina Jolie 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, earning $237 million internationally.

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Angelina Jolie - Girl, Interrupted

Angelina Jolie took the supporting role of the sociopathic Lisa Rowe 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 Winona Ryder played the main character in what was hoped to be a comeback for Jolie, the film instead marked her final breakthrough in Hollywood. Angelina Jolie won her 3rd Golden Globe, her 2nd 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".

Angelina Jolie - Critics in Pushing Tin and The Bone Collector

In 1999, Angelina Jolie starred in Mike Newell's comedy-drama Pushing Tin, co-starring John Cusack, Billy Bob Thornton, & Cate Blanchett. She played Thornton's seductive wife. The film received a lukewarm reception from critics and Angelina 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."

Angelina Jolie then worked with Denzel Washington in The Bone Collector (1999), an adapted crime novel written by Jeffery Deaver. She played Amelia Donaghy, a police officer haunted by Amelia' cop father's suicide, whoshe 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."

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Angelina Jolie - as Gloria McNeary in Hell's Kitchen

Angelina Jolie returned to film as Gloria McNeary in the 1998 gangster movie Hell's Kitchen, and later that year 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 Angelina 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." She won the Breakthrough Performance Award by the National Board of Review.

Angelina Jolie had "nothing else to give".

Following Gia, Angelina Jolie moved to New York and stopped acting for a short period of time, because she felt that she had "nothing else to give".

Angelina Jolie enrolled at New York University to study filmmaking and attended writing classes.

Jolie described it as "just good for me to collect myself" on Inside the Actors Studio.

Angelina Jolie - starred in HBO's Gia

In 1998, Angelina Jolie starred in HBO's Gia, portraying supermodel Gia Carangi. The film depicted a world of s_x, dr_gs 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 Angelina Jolie role as the titular Gia, and it's easy to see why. She 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 2nd consecutive year, Angelina won a Golden Globe and was nominated for an Emmy. Angelina also won her 1st Screen Actors Guild Award. In accordance with Lee Strasberg's method acting Jolie reportedly 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, Jolie 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.'"

Angelina Jolie - Breakthrough

Angelina Jolie's career prospects began to improve after Jolie' performance as Cornelia Wallace in the 1997 biographical film George Wallace for which she won a Golden Globe Award and was nominated for an Emmy. The film was praised by critics and, among other awards, received the Golden Globe for Best Miniseries/Motion Picture made for TV.

Angelina Jolie played the 2nd 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.