Before Catherine Hardwicke and Amanda Seyfried were reimagining the age-old fairytale, Witherspoon starred in a modern update of Little Red Riding Hood.
She plays Vanessa Lutz, a trailer-trash teen from LA making her way to her grandmother's house; Kiefer Sutherland plays serial killer Bob Wolverton, whom Vanessa will run into en route. Slightly silly and OTT it may be (Vanessa's gang member boyfriend is called Chopper Wood), but it's well worth a look.
Smart Blonde? She was showing a predilection for offbeat material.