8. New York, New York

Vehicle: 1965 Chrysler New Yorker
Auction Link
Notable Features: Fully restored, featured in the film Girl, Interrupted starring Winona Ryder and Angelina Jolie
Complex Says: We're not sure you'd want to try to park this in modern-day New York, but it's still a great car of its type. It comes with documentation to back its claims to movie provenance, so you might want to jump on this if you're a film vehicle collector.