The Johnny Cash songs work for the achievement. I got it after playing I Walk The Line.
Did you try sorting by year in-game? I'm pretty sure I saw Ooby Dooby listed under 1950whatever, but I know I saw the Johnny Cash songs according.y
No, Ooby Dooby was confirmed not to work since before the game's release.
But some Johnny Cash (not Ring of Fire, but definitely I Walk The Line) get the achievement.
Cry Cry Cry (Johnny Cash) Works for the achievement :D
Yup :D I walk the line is under 1956 win