At the start of the game you will go to the local diner to collect the keys off stucky. At the far left are two old men, one will request a song on the juke box. walk up to the juke box press a to start the record. the record will get stuck so keep tapping the a button to give it a thump.
In chapter 5 you will start in prison. when you get out you will proceed to the town, just as you come to the end of the main street, you will again see the diner on the left hand side. Go in and again go to the juke box. play the song again for the achievement.