This achievement is an easy achievement.
Make sure that the song selection is ordered by song and not by artist, you can do this with
.( thanks to SuperModelZX for pointing this out)
Then all you have to do is press
(R2) on your controler (that's the shuffle button) while in the song selection screen. Then you need to start and finish this song.
Repeat the steps above for 5 times.
After doing this you should get the trophy.