The busy actress was then chosen by novice director Goldie Hawn for the pivotal role of a pre-teen coming of age who takes a stand against bigotry in Arkansas in "Hope" (TNT, 1997). Malone then landed a key role alongside Susan Sarandon and Julia Roberts in "Stepmom" (1998), and was particularly effective playing Sarandon's young daughter who struggles to find a place in her life for her new young stepmother (Roberts). Shortly after that film's success, Malone sparked headlines in Hollywood in 1999 when she Filed suit against her mother Debbie, charging mismanagement of her earnings, failure to pay taxes, and seeking emancipation--her legal bid ended in early 2000 when at age 16 she won legal emancipation from her mother, who was barred from interfering with the actress' career and earnings.

Featured and leading roles in other films--including "For Love of the Game" (1999) as Kelly Preston's daughter, "The Book of Stars" (2001) opposite Mary Stuart Masterson and the telepics "Cheaters" (2000) and "The Ballad of Lucy Whipple" (2001) opposite Glen Close--continued to come in. Malone had a breakthrough year in 2001 when she played the girlfriend to a pair of young misfits in two critically hailed films: first, she was the love interest to Jake Gyllenhaal's distrubed "Donnie Darko;" next, she played Hayden Christensen's neighbor who talks his father (Kevin Kline) into a kiss to see what her mother, Kline's ex-flame, might have felt, in "Life as a House." Both films showcased Malone's continually evolving natural screen presence, and her penchant for demonstrating a wisdom beyond her years. She was praised by critics for providing perhaps the best performance in her next film, "The Dangerous Lives of Altar Boys" (2002), which also starred Jodie Foster--indeed, with her continuously mature choices, Malone seemed to be heading toward the same kind of child-star-curse-beating career glories that Foster herself had pioneered. Expanding her reperoire, Malone executive produced her next feature, the dark comedy "American Girl" (2002), in which she played a trailer park-living, semi-suicidal pregnant 15-year-old enduring all sorts of Jerry Springer-esque family melodram; the film never found a theatrical distributor, however.

Malone continued to equate herself well in a series of supporting roles in movies of larger scale, including the CBS TV biopic "Hitler: The Rise of Evil" (2003), "Cold Mountain" (2003) and the too-sombre "The United States of Leland" (2004), playing the drug addicted sister of an autistric youth murdered by her ex-boyfriend. In 2004 the actress delivered perhaps her best performance yet in "Saved!" (2004), an indie meditation on morality and the religious right disguised as a teen comedy. Although the film suffered a bit from its one-note agenda, Malone was pitch-perfect as Mary, the once-popular schoolgirl at a Christian high school whose comes to re-examine her life and faith after being ostracized for becoming pregnant in a misguided bid to "cure" her boyfriend's homosexuality. Next was a high-spirited turn as the flirtatious, impulsive Lydia Bennett, the young sister of Elizabeth (Keira Knightley) who nearly leads the family to ruin in the lively 2005 adaptation of Jane Austen's classic "Pride and Prejudice."