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)

Nick Pellegrino

High School Vice Principal (uncredited)

Ray Conchado

Partygoer (uncredited)