Similar to Manager of Fate but this time you create a random playlist, you still need to 5 star all songs though, so if you aren’t able to 5 star all songs on your current difficulty, it might be an idea to drop down one. To create a random playlist go to quickplay and press green to bring up the play song menu on the right, select “Random Songs” and the choose 5. Once you have completed the playlist and 5 starred all songs the achievement is yours.
Note: If you are getting to the end of a song and don't think you will 5 star it, you can pause and restart. This will not affect the achievement.