Car No 13 is a 1948 Cadillac Series 61 fastback coupe and Tuner No8 are The Andrews Sisters who apparently sang about a Cadillac in the Spring, 1947 song: The Lady From 29 Palms
Car No 2 is a Curved Dash Oldsmobile. And then there was the song: My merry Oldsmobile in 1905 so I think the match is No6, who I believe is Gus Edwards.
Tuner No5 is Robert Johnson who sang Terraplane Blues, which matches Car No3 a 1935 Terraplane DeLuxe Six convertible coupe
Tuner No10 shows The Playmates, who had a song, "Beep beep" mentioning a Nash Rambler, a reference to Car No1, a Nash Rambler Convertible Landau, 1951.
Tuner No13 and Car4: Sonny Boy Williamson who in "Brother James" mentioned a 1929 Ford, which happens to be Car4: 1929 Ford Model A Coupe.