shuffle songs in itunes

1. Start by turning on the top menu bar, by using CTRL+B.
2. Then, in the Songs section; select Controls/Shuffle/Turn On Shuffle.

Notice in the screenshot above, that the Now Playing area is empty (because nothing is being played!)

Alternatively, select a song to play. Once you do that, simply click on the Shuffle icon in the Now Playing;

so that it turns blue...

and iTunes will shuffle through the entire Library - except for songs that are not ticked or have Skip on Shuffling set on.

If there's a reason that somebody would want iTunes to EVER hide that top menu bar, I'd like to hear about it. Apple needs to get a clue. Intuitively is how we want to do it. CTRL+B, really???

Here's how I got all of my music to shuffle (yes, the old way is better) but this isn't totally awful either:

1. go to My Music and at the top center of the screen change the drop down to Songs

2. Click any song in the list (or click a song you like)

3. When it starts playing, hit the small bar at the bottom of the screen showing the title of the song

4. click the shuffle button on the left to make sure it's darkened

At least 60% of the time it works every time.

No seriously, it works.