Crossroads

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