In 1999 Phillips released her debut album "I'd Rather Eat Glass" and had her first onscreen role with a cameo in the Alison Anders/Kurt Voss music industry comedy "Sugar Town". Now the performer had work of her own to address, and was clear in interviews that the wild life she had reveled in previously was behind her. She next took a starring role in James Toback's mostly ad-libbed 2000 feature "Black and White", starring as Charlie, an Upper East Side rich girl who appropriates African-American hip-hop lifestyle along with her similarly privileged friends. The film's daring opening scene featured her in an a menage-a-trois in Central Park with rapper Power and actress Kim Mutalova. Phillips was next seen as one of the "band aids", a group of girls who followed rock musicians around on tour in "Almost Famous" (2000) and then turned up as a teenage prostitute who runs afoul of the title character in "Bully" (2001).