12. Patrick Dempsey as Bobby Libner, Coupe de Ville (1990)
The Libner brothers have never gotten along, a fact their father is fully aware of when he tasks all three of them with the mission to transport a mint condition Cadillac halfway across the country as a gift to their mom. The youngest brother, Bobby, is stereotypically disagreeable, the type of reform school troublemaker who's seen Rebel Without a Cause one too many times. If we were his brothers (Daniel Stern, Arye Gross), a couple days in we might have left him stranded somewhere between Detroit and Miami and let him try his bad-boy luck hitchhiking.