One of my favorites is Two Lane Blacktop with Warren Oates and James Taylor. Oates is driving a 1970 GTO Judge and Taylor has a 1955 Chevy.
In this cult favorite road film, a mechanic (Dennis Wilson) and a driver (James Taylor) live only to race and maintain their 1955 Chevy. Heading east from California with no particular agenda, they give a girl (Laurie Bird) a ride, and en route she incites jealousy between the men by sleeping with them both. Meanwhile, the trio encounters an overbearing GTO driver (Warren Oates) who agrees to race them to New York, each side putting at stake their most prized possession: their car.