Lucy

Britney Spears

Kit

Zoe Saldaña

Ben

Anson Mount

Mimi

Taryn Manning

Caroline

Kim Cattrall

Pete Wagner

Dan Aykroyd

Henry

Justin Long

Kit's Mother

Beverly Johnson

Ms. Jenson

Bahni Turpin

Bar Owner

Kool Mo Dee

Dylan

Richard Voll

Young Lucy Wagner

Jamie Lynn Spears

Dylan's Other Girl

Katherine Boecher

Bar Patron

Dave Allen

High School Burnout

Kyle Davis

Kurt

Branden Williams

Kit's Friend

Celina Belizan

Travis

Raymond Young

Kit's Friend

Shonda Farr

Bar Patron

David "Gruber" Allen

Graduation Band

Jaret Reddick

Graduation Band

Christopher Van Malmsteen

Graduation Band

Erik Rodham Clinton

Graduation Band

Gary Wiseass

Customer

Ritchie Montgomery

Guy in Bar

Brandon Henschel

Annie

Janet May

Talent Organizer

Seth Romatelli

Audition Applicant

Jesse Camp

Young Kit

Dajine Colon

Young Mimi

Crystal Milton

Kit's Father (uncredited)

Cullen G. Chambers

High School Vice Principal (uncredited)

Nick Pellegrino

Partygoer (uncredited)

Ray Conchado