How do you shuffle songs in iTunes?

Are you sure?

When you click on the Shuffle icon (ringed)...

it should turn blue, but the same song will continue to play. But if you compare the list on the Up Next icon (arrowed), it will show different lists;

In the screenshot above (shuffle is off), the Up Next list is the same as the song order list underneath "Heaven is 10 zillion...".

But with Shuffle on, the list shows...

a random "shuffe" list of songs.

I have the same problem and this is what i have.

Check the other songs, to see if they are set to Skip when shuffling. If they are, that's why the list is empty.

Highlight a song, select File/Get Info/Options>Skip when shuffling. The box should be empty, like this;

If you choose several items at the same time, the skip when shuflfing changes to this:

and you need to change the drop-down to Yes, then back to No - to make sure every track is set to No.

Sultdog wrote:

Ever since I installed the newest version of iTunes, I am unable to shuffle songs within each of my playlists. When I go from Shuffle Off to Shuffle On, nothing happens.

When you play the songs, does it jump around when changing songs?

The behavior of shuffle playlists has definitely changed. In the past I had a procedure in iTunes:

1. Populate Playlist 1 with a collection of podcast episodes.
2. Manually arrange Playlist 1 to a desired play order, usually semi-chronological.
3. Populate Playlist 2 with a collection of music.
4. Turn on shuffle for Playlist 2 and copy the shuffled order to the play order
5. Drag the contents of Playlist 2 (music) to Playlist 1 (podcasts)
6. Weave the random music into the chronological podcasts to produce a playlist of chronologically ordered podcasts alternating with random music.

Step 4 no longer works. Shuffle a playlist in iTunes no longer simply rearranges the order of the playlist, it simply begins playing in the random order. The only workaround I have found is to turn on shuffle in my music playlist and then drag the "up next" list to my podcat playlist. This works but requires more steps because the "up next" list is only 20 items long.

What a pain!