She had more luck with the ensemble comedy-drama Playing By Heart (1998), appearing alongside such heavy-hitters as Sean Connery and Gena Rowlands. In 1999, Jolie appeared in three major films: the disappointing comedy Pushing Tin, co-starring John Cusack, Billy Bob Thornton, and Cate Blanchett; The Bone Collector, a thriller co-starring Denzel Washington; and Girl, Interrupted, co-starring Winona Ryder. In the latter film, Jolie’s performance as Lisa, a charismatic sociopathic inmate in a psychiatric hospital, earned her rave reviews, a third straight Golden Globe, and an Academy Award for Best Supporting Actress.

In 2000, Jolie stars with Nicolas Cage in the action-packed Gone in Sixty Seconds and with Antonio Banderas in the period drama Dancing in the Dark.

After her divorce from Miller, Jolie was romantically linked to her Playing God co-star and veteran “bad boy” Hutton; they reportedly broke up in 1999. In the spring of 2000, she began dating her Pushing Tin co-star and fellow Oscar winner (Best Adapted Screenplay for 1997's Sling Blade) Thornton. The couple were married (she for the second time, he for the fifth) on May 5, 2000, in Las Vegas.