This is a two part misseable achievement. In order to get this, you must use the juke box twice in the game, at two totally different sections.
The first time you will enter the diner is early on in episode 1, after Alan and Alice get off the Ferry. The Andersens will be be sat near the juke box and after some banter, a kick of the machine and some more banter, the music will play.
The second part of this achievement is much later on in the game, episode 5 to be precise, when you have to traipse through Bright Falls at night with the Sheriff. After opening the gate and reaching the main road with the possessed float. Head left and before you head off that road, there is a diner on the left hand side of the road. In the corner. It's the same diner as in episode 1. Simply go in, switch it on and the achievement should unlock. No idea as to whether you can get it in two different playthroughs, that currently is unknown, so make sure you grab it the first time through.