Phillips made her singing debut with I'd Rather Eat Glass (1999), and since her first major film appearance in Black and White (1999), she has acted in Almost Famous (2000), Bully (2001), The Door in the Floor (2004), Havoc (2005), Hostel: Part II (2007), and Choke (2008).
Her father won custody when she was in third grade[clarification needed], and she moved with him to Lloyd Harbor, a village of the Town of Huntington, Long Island.
[5] Once described by The Observer as a "wild child", she experienced a rebellious childhood in New York City, where she used to party, drink and take drugs, such as cocaine, ecstasy, and heroin.
[5] On this period of her life, she remarked: "If you were 14 years old and able to live on your own in an apartment in New York City, and you got invited to all these clubs, and you got a bank account and you had a car service you could call so that you could go wherever you wanted ... What would happen?
"[citation needed] After signing a record deal at age 17, Phillips began working on her debut album I'd Rather Eat Glass, produced by Jerry Harrison.
Phillips collaborated with a number of artists when writing songs for the album, including Eric Bazilian, Greg Wells, Dave Bassett, Howard Jones and Jill Cunniff.
In Tart, opposite Dominique Swain and Melanie Griffith, she played the longtime friend of a young woman at a preparatory school in 1980s New York City.
In 2003, Phillips starred alongside Mischa Barton as a member of a bizarre cult of young criminals in the thriller Octane, which premiered at the Cannes Film Festival.
In 2004, she played the nanny of an author's young daughter, with Jeff Bridges and Kim Basinger, in The Door in the Floor (2004), a drama with heavy sexual themes adapted from the novel A Widow for One Year by John Irving.
[18] The biographical film What We Do Is Secret featured Phillips as Lorna Doom, the Germs' bassist and a close friend of singer Darby Crash.
Director Rodger Grossman cast Phillips when she was 17 years old, and she stayed committed to the project for almost a decade as he worked to bring the film into production.
[19] She received critical acclaim for her portrayal; Phil Gallo for Variety found her performance to be "striking" and stated that her character "lights up in a unique way whenever she's in Crash's company or simply talking about him".
[3] She also starred, opposite Sam Rockwell and Anjelica Huston, as a milkmaid in the well-received black comedy Choke, based on the Chuck Palahniuk's novel of the same name.
Her first release in the year was the romantic comedy Wake, in which she played an emotionally isolated modern woman who meets a man mourning his fiancée at a funeral.
Dread Central, in its review for the film, noted: "Bijou Philips is undoubtedly the star here, jumping into her role in what is admittedly just a piece of schlock cinema with great aplomb".
In FOX's sitcom Raising Hope (2010–2014), Phillips played the title character's biological mother, a serial killer sentenced to death.
In 2010 and 2012, she guest-starred in episodes of the police procedural television series Hawaii Five-0 and Law & Order: Special Victims Unit, and in 2011 she appeared in the video for Broken Social Scene's song "Sweetest Kill".
[31][32] The same month, actress Heather Matarazzo claimed that Phillips had held her against a wall and choked her shortly before filming for Hostel: Part II began.