iTunes shuffle not working in playlists?

[jon08]

Why does the shuffle option not work when I have the playlist arranged by Artist (so from A-Z) or by anything else?

The shuffle will only work if an arrow will be pointing upwards or downwards as seen in the snapshot.

Why can't I have it arranged by the artist though? I much prefer it that way.

 

[Jolly Giant]

IIRC, shuffle will only work if all tracks in the playlist are checked (arrow pointing upwards).

if you don't want specific tracks in the playlist, remove them rather than unchecking them.