Christina Ricci as Elizabeth Wurtzel

Jason Biggs as Rafe

Anne Heche as Dr. Sterling

Michelle Williams as Ruby

Jonathan Rhys Meyers as Noah

Jessica Lange as Mrs. Wurtzel

Lou Reed as Lou Reed

Jesse Moss as Sam

Nicholas Campbell as Donald

Zoe Miller as Elizabeth at 12

Sheila Paterson as Grandmother

Rob Freeman as Mister Cool

Nicole Parker as Waitress

Frida Betrani as Julia

Klodyne Rodney as Nurse

Ian Tracey as Rolling Stone Editor

Wendy Noel as Mrs. Edelman

Bill Marchant as Lecturer

Tom Kent as Lecturer

Christine Anton as Mrs. Stevenson

Cindy Lentol as Sheryl

Paula Plum as Geeky Mom

Paul Hoover as Geeky Dad

Tammy Bentz as Announcer

Emily Perkins as Ellen

Maddy Capozzi as Amy

Claude de Martino as Grandfather

Charles Andre as Mugger

Mike Mitchell as Purse Snatcher

Brad Swaile as Student

Charles Siegel as Dr. Isaacs

Charles Singh as Khalil

Chiara Zanni as Ruby's Roommate

Stephen Basilone as Warren

Devon Diep as Student (uncredited)

Jack Fleischer as Harvard Student (uncredited)

Colby Johannson as Frat Guy (uncredited)

Alma Martinez as Professor (uncredited)

Josh Mead as Frat Guy (uncredited)

Todd Poudrier as Law Student (uncredited)

Jennifer Rappo as Student (uncredited)

Ron Truppa as Harvard Undergrad (uncredited)

Andrew Washington as Student (uncredited)