Lindsay Lohan as Anna Coleman

Jamie Lee Curtis as Tess Coleman

Harold Gould as Grandpa

Chad Michael Murray as Jake

Mark Harmon as Ryan

Stephen Tobolowsky as Mr. Bates

Christina Vidal as Maddie

Ryan Malgarini as Harry Coleman

Haley Hudson as Peg

Rosalind Chao as Pei-Pei

Lucille Soong as Pei-Pei's Mom

Willie Garson as Evan

Dina Spybey-Waters as Dottie Robertson

Julie Gonzalo as Stacey Hinkhouse

Christina Marie Walter as Same Shirt Girl

Lu Elrod as Detention Monitor

Heather Hach as Gym Teacher

Lorna Scott as Butcher Woman

Chris Carlberg as Ethan - Drummer

Danny Rubin as Scott - Bass Player

Hayden Tank as Harry's Friend #1

Cayden Boyd as Harry's Friend #2

Marc McClure as Boris

Chris Heuisler as Mr. Waters

Jeffrey Marcus as Depressed Patient

Jacqueline Heinze as Crying Patient

Mary Ellen Trainor as Diary Reading Patient

Erica Gimpel as Harry's Teacher

William Caploe as Talk Show P.A.

Daniel Raymont as Makeup Artist

Veronica Brooks as Champagne Waitress

Lee Burns as Bouncer

Amir Derakh as House of Blues Emcee

Zoe Waters as Wedding Baby