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Dry-docked in the Editor's section while some re-post issues are addressed.
Artist 1, Billy Murray, should go with Car Song 3, the 1966 Oldsmobile full size. It's as merry an Oldsmobile as another.
Artist 3, David Hasselhoff, must obviously go with Car Tunes 8, "Jump in my Car", the car being Kitt, natch'rally.
Artists 6 are The Happiness Boys, going with Car Song 2 "Since Henry Ford Apologized To Me" (since we already had "Henry's Made A Mady Out Of Lizzie" in another puzzle, it may be the right guess, doesn't it?)
ThirdCarTunesArtist 2 is Soul and R&B band Rose Royce. They should match with ThirdCarTunesSong 10, as their most successful hit single was Car Wash (1976).
No9: Merrill Moore, Car No12: Old Men and Old Women Are Going Home on the Street Car I kid you not, this was a song
Artist 8 is Luke McDaniel, but I didn't find the right song yet.
Artist No5 is the Southern Culture on the Skids
... and Car/Song 3(is) about an Oldsmobile, but that's not a song in this puzzle.
Not "In my merry Oldsmobile", and not to be paired with Jimmy Murray?
If so , I'd say that Car/Song 3 (1966 Olds 88) is "Roughouse 88", a 1969 LP by Artist 9, Merrill Moore.
Billy Murray (Artist 1) has already been identified, but to go with him, how about Song 12 "Gasoline Gus and his Jitney Bus" (1915)?