I le 1999, na avea ai Jolie ma tagata lagolago o se tagata maʻi mafaufau i le Girl, Interrupted (1999), o se fetuunaiga o le Susanna Kaysen's memoir of the same name. E ui o Winona Ryder na taalo i le tagata autu i le mea na faamoemoe e toe foi mai mo ia, ae o le ata na faailogaina ai le manumalo mulimuli a Jolie i Hollywood. Na ia manumalo i lona tolu Golden Globe Award, lona lua Screen Actors Guild Award, ma le Academy Award mo le Best Supporting Actress. Mo Variety, Emanuel Levy na matauina, "Jolie o le flamboyant, irresponsible girl who turns out to be far more instrumental than the doctors in Susanna's rehabilitation". I le 2000, Jolie na aliali mai i lana muamua taumafanafana blockbuster, Gone in 60 Seconds, lea na avea ai ma ana ata sili ona maualuga na maua i le lalolagi atoa, ma maua ai le $ 7.23 miliona. O ia na faia se matafaioi mulimuli a Jolie i Hollywood. Na ia manumalo i lona tolu Golden Globe Award, lona lua Screen Actors Guild Award, ma le Academy
Golden Globe Award, lona lua Screen Actors Guild Award, ma le Academy Award mo le Best Supporting Actress.