442… 1965 Olds Cutlass Holiday coupe
Mick Jagger getting out of his 1969 Rambler American
Presenting the Mustang… 1964 1/2 billboard
Submission from the UK:
Wolseley 6/110, unfamiliar english brand not sold in the US. Tailfins, lots of chrome trim, and traditional grille. I had to wikipedia this car, and was surprised to learn that the styling credit goes to none other than Pininfarina!!
Carefree companion… 1948 Jeepster