Arcade Paradise

You do not need to listen to the entire duration of each song for the achievement, only the goals. Simply flipping through each album and pressing play was enough to unlock this for me. Note that additional songs are available to purchase from the office PC.

LDNS FINESTT has pointed out in the comments that if you save up enough to buy all the songs, you can listen to them for the achievement and then quit. Since your progress saves at the end of each day when you launch the game again your money will be restored.

If you'd like to keep the tracks and need additional currency the remainder of this achievement unlock shares the same solution as

Shortly into the story you will unlock the ability to complete "To-Do" tasks. You get 3 per day and each has a varying amount of Pounds (£) you can use to purchase upgrades on the office PC and songs from the Jukebox. To-Do list items will vary between collecting money, doing laundry, getting specific scores in games, and there's even one to just walk down the street. You can grind this out semi-quickly by completing the tasks asked and ending the day early, or if the tasks are undesirable you can quit out of the game and restart the day to get a different set.