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This is a two part achievement, and failing to do either part negates you from obtaining it during your play through and you will have to start all over. You must use the Juke Box in the diner twice at two completely separate instances.
The first time will be during Episode 1, after Alan and Alice get off the Ferry. The Andersons will be near the Juke Box and ask you to play a song for them. Oblige by going up to the Juke Box and pressing B.
The second time will be during Episode 5, you will be with the Sherrif. After you open the gate and reach the main road, head left and go into the diner; which is clearly visible as long as you're looking at the store signs. Go inside and switch on the Juke Box. If you're following the collectible guide, you'll have to go in here anyway.