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Play songs in playlist randomly without repeating

I have songs in a playlist that I want to play randomly one after another until the list is completed without replaying any of the songs. How can I set iTunes to do this?

Windows, Windows 6

Posted on May 26, 2020 10:40 AM

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Posted on May 27, 2020 12:10 PM

Sorry for the delay, this post took longer to write than I expected.


You want to be able to come back to the same Playlist on a subsequent day (or even when re-starting iTunes on the same day), but not hear the songs you heard before.


(Almost) very easy to achieve.


First though, note what will happen when you re-open iTunes:

    • the player will still be in Shuffle mode
    • the remaining songs from the previous day will not be in the Up Next queue, or separately listed. (All is not lost)


Let's suppose (that on day one) you have been playing your three hour playlist, but now (on day two) want to continue that list. Create a Smart Playlist

    • Click on File/New/Smart Playlist. You will see a window like the one below:



    • Change the options, by choosing from the drop-down menus or typing in, as appropriate, so that your window looks like the one shown below - but:
      • in the box that says Ambient Chill (27 @ 3hr32m), choose your target Playlist from your drop-down menu
      • click on the + icon (as shown in screenshot) to add a new rule, which will be the next step
      • you choose the number of weeks, or days or even months*
      • it should now look like the one below:



    • Click OK
    • The Playlist will now be shown. You can type in a name for it if you wish, or leave it as the default
    • That's it


How does it work (you ask)?

    • you use this Smart Playlist to play the actual Playlist you want to hear
    • once a song has been played, it is removed from this Smart Playlist
    • it will not be put back into the Smart Playlist until 2 days have elapsed since it was last played
    • this means that even if you create this Smart playlist on day two, it will exclude songs that you played on day one
    • simply start this temporary Smart Playlist playing. It will not have any of yesterday's songs in it. However, see the caveat below


* The Caveat:

    • if you wish to play this Smart Playlist after two or three days, edit the Smart Playlist to reflect the revised number of days
    • a slight limitation of this is that if any song from the original Playlist has been played within the time limit you set, it will be excluded from the temporary list, so you won't hear it this time. This might happen if the song is in more than one Playlist or you simply played it recently


Will this work for you?

8 replies
Question marked as Best reply

May 27, 2020 12:10 PM in response to the fiend

Sorry for the delay, this post took longer to write than I expected.


You want to be able to come back to the same Playlist on a subsequent day (or even when re-starting iTunes on the same day), but not hear the songs you heard before.


(Almost) very easy to achieve.


First though, note what will happen when you re-open iTunes:

    • the player will still be in Shuffle mode
    • the remaining songs from the previous day will not be in the Up Next queue, or separately listed. (All is not lost)


Let's suppose (that on day one) you have been playing your three hour playlist, but now (on day two) want to continue that list. Create a Smart Playlist

    • Click on File/New/Smart Playlist. You will see a window like the one below:



    • Change the options, by choosing from the drop-down menus or typing in, as appropriate, so that your window looks like the one shown below - but:
      • in the box that says Ambient Chill (27 @ 3hr32m), choose your target Playlist from your drop-down menu
      • click on the + icon (as shown in screenshot) to add a new rule, which will be the next step
      • you choose the number of weeks, or days or even months*
      • it should now look like the one below:



    • Click OK
    • The Playlist will now be shown. You can type in a name for it if you wish, or leave it as the default
    • That's it


How does it work (you ask)?

    • you use this Smart Playlist to play the actual Playlist you want to hear
    • once a song has been played, it is removed from this Smart Playlist
    • it will not be put back into the Smart Playlist until 2 days have elapsed since it was last played
    • this means that even if you create this Smart playlist on day two, it will exclude songs that you played on day one
    • simply start this temporary Smart Playlist playing. It will not have any of yesterday's songs in it. However, see the caveat below


* The Caveat:

    • if you wish to play this Smart Playlist after two or three days, edit the Smart Playlist to reflect the revised number of days
    • a slight limitation of this is that if any song from the original Playlist has been played within the time limit you set, it will be excluded from the temporary list, so you won't hear it this time. This might happen if the song is in more than one Playlist or you simply played it recently


Will this work for you?

May 26, 2020 10:15 PM in response to TedinTO

Set iTunes to play the Playlist in shuffle mode.


  • if there is a song title in the Now Playing window (at the top of iTunes), then either that song is playing or the player is in pause mode. Click on Controls/Stop (or use CTRL+. - that's the Control button and the full stop key (period key) to stop the song and clear it from the Now Playing window




  • when the Apple logo is displayed in the Now Playing window, that means nothing is playing or paused, so proceed to the next step
  • Click on Controls/Shuffle/On
  • select the Playlist that you wish to play from the list on the left hand side of your iTunes window
  • click on Play
  • That's it. iTunes will start the Playlist with a random song and the play the rest at random - or Shuffle mode. You can use the Up Next queue to see what is going to play and when


Each song will be played once and when the list finishes, the player will stop.

May 27, 2020 11:15 AM in response to TedinTO

All you ask for (in this discussion) will be granted. I can't help with the meaning of life though.


TedinTO wrote:
Presumably this ensures that the songs do not replay during one session.

Correct. Definitely!


You can see what is due to play by clicking on the Up Next icon (which I referenced in the screenshot in my previous post). Look at the screenshot below, of the same Playlist:



  • The dark background on the Shuffle icon indicates that the player is in Shuffle mode
  • You can click on that icon to turn shuffle off. However, when the player is in full stop mode, the Shuffle icon is not displayed, which means that you have to use Controls/Shuffle/On to turn it on at the beginning
  • In the screenshot above, track seven has already played, so it's missing from the Up Next list. It will not be played again (in this session)
  • Track one is now playing, so it's not in the Up Next list either.
  • To complete the play order, (we've had tracks 7 & 1), the remaining order is tracks 3, 2,5,4 & 6
  • After track six has been played, the player will stop


Don't worry, I haven't finished yet, although I may need to create two posts.


Here's an important note about repeat:

Importantly, to avoid any songs being played again in this session, make sure that the Repeat function is off. Look in the Now Playing window, at the right hand end, above the time -8:07. That's the Repeat icon. If it was on, it would have the dark grey background, like the Shuffle button. Also, crucial to note, if Repeat is on, when you click once on that icon it will go into Repeat 1 mode. Repeat 1 simply repeats the same song, over and over again. Click it yet again to turn Repeat off. Here's a screenshot after I turn on Repeat mode:



As you can see, the song that is currently playing will be played again. In fact, if you look towards the bottom of that Up Next list, the song Sympathy will be played twice in a row. That's probably because it's a short Playlist.


So to achieve what you want, make sure you do not turn on Repeat mode or have it in Repeat 1 mode.


See next post.




May 27, 2020 8:21 AM in response to the fiend

Thank you for the response.


Presumably this ensures that the songs do not replay during one session.


I would like to be able to close the application one day and on the following (or a subsequent) day resume playing the same list without hearing any of the songs that I heard during the previous session.


Is this possible; and if so, how do I proceed to make it so?


Thank you.

Play songs in playlist randomly without repeating

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