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In iTunes 11, let's say I'm playing Song X by Artist A.

I have a few more albums by Artist A, and decide I want to hear some more of their stuff, but I'd like to hear it at random.

If I switch to the Artists view, I can select Artist A and hit Shuffle, but that will immediately start playing random tracks by the artist, eliminating whatever I already had playing.

I can also pick Add Artist A to Up Next from the context menu, but this will add all their songs in order to Up Next.

Can I have my cake and eat it too, somehow? Can I both maintain the currently playing song and enqueue the shuffled set of Artist A's songs to play Up Next?

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up vote 9 down vote accepted

You can option-click the shuffle button at the top of an album to queue it in a random order. Oddly, if I do that for the artist it only adds the first song in the list. Weird. And you can't intermingle different albums like this, you have to do that manually in the Up Next panel.

Correction: if you go to Artists view, select All Artists and then option-click the shuffle button next to one of the artist names, it will queue all the songs by that artist in a random order. If you select an individual artist and do it, it will only queue the first song.

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Bam. Your correction does exactly what I want: it enqueues all the artist's songs (though it includes the currently-playing one) without interrupting the current track. That'll do. :) – Dan J Jun 6 '13 at 4:52

I think the ability to shuffle particularly in the upnext panel is not there in iTunes. However you can select Upnext and manually drag and rearrange the songs. I know this is a pain but hopefully Apple will update the shuffle feature for Upnext in a future iTunes update.

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As far as being able to shuffle the "Up Next" tracks, I've found it quite simple to select all those tracks in "up next" and drag into a new playlist. From there of course it can be shuffled by song or album (Controls > Shuffle...). Its technically a workaround and I too hope "Apple will update the shuffle feature for Upnext in a future iTunes update."

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Tip: just drag any song/album/artist to the right side of the window and a new playlist will be created. I just did that instead of adding the songs to Up Next and then create a playlist. – Feb 13 '14 at 16:16

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