Britney Spears
Lucy Wagner
Zoe Saldaña
Kit
Taryn Manning
Mimi
Anson Mount
Ben
Dan Aykroyd
Pete Wagner
Kim Cattrall
Caroline
Justin Long
Henry
Beverly Johnson
Kit's Mom
Bahni Turpin
Ms. Jenson
Kool Moe Dee
Bar Owner
Richard Voll
Dylan
Katherine Boecher
Dylan's Other Girl
Dave Allen
Bar Patron
Kyle Davis
High School Burnout
Branden Williams
Kurt
Celina Belizan
Kit's Friend
Shonda Farr
Kit's Friend
Jaret Reddick
Graduation Band
Christopher Van Malmsteen
Graduation Band
Erik Rodham Clinton
Graduation Band
Gary Wiseass
Graduation Band
Ritchie Montgomery
Customer
Brandon Henschel
Guy in Bar
Janet May
Annie
Seth Romatelli
Talent Organizer
Jesse Camp
Audition Applicant
Jamie Lynn Spears
Young Lucy Wagner
Dajine Colon
Young Kit
Crystal Milton
Young Mimi
Cullen G. Chambers
Kit's Father (uncredited)
Carl Conti
Paramedic (uncredited)
Nick Pellegrino
High School Vice Principal (uncredited)