Angelina Jolie critic Peter Stack 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 from the National Board of Review. In 1999, Jolie starred in the comedy-drama "Pushing Tin", alongside John Cusack, Billy Bob Thornton, and Cate Blanchett. The film met with mixed reception from critics, and Jolie's character—Thornton's seductive wife—was particularly criticized; writing for "The Washington Post", Desson Howe dismissed her as "a completely ludicrous writer's creation of a free-spirited woman who weeps over hibiscus plants that die, wears lots of
Angelina Jolie felt that she had "nothing else to give." She separated from Miller and moved to New York, where she took night classes at New York University to study directing and screenwriting. Encouraged by her Golden Globe Award win for "George Wallace" and the positive critical reception of "Gia", Jolie resumed her career. Following the previously filmed gangster film "Hell's Kitchen" (1998), Jolie returned to the screen in "Playing by Heart" (1998), part of an ensemble cast that included Sean Connery, Gillian Anderson, and Ryan Phillippe. The film received predominantly positive reviews, and Jolie was praised in particular; "San Francisco Chronicle"