I have a Mac and I listen to music in iTunes most of time. After quite a bit of experimentation I have, I think, finally come across a way of creating a play list that allows me to tolerate iTunes. I don’t like listening to my music in order. I’d like it to play randomly. On the other hand, random typically means I get one or two songs I don’t particularly like that come up often and some songs I do like getting played almost never. This is never what I want, but this is exactly what the useless “Party Shuffle” feature of iTunes. I hate it. Even with the “don’t play a song by the same whatever” settings set, it still manages to do so too often for my to tolerate.
My solution is to put together a play list that contains a set of music I like to listen to and then I create a smart play list based on it. When configured correctly, my play list will play all the music I want to hear regularly, but not too regularly. Here’s how I do it. I create a smart play list and set it to match all of these rules:
- First, I add the rules that pick out genre or off of another play list as the source, plus any other modifications like minimum rating.
- Second, set a rule that requires the Last Played date is not in the last X days, where X depends on the size of the source play list. For example, my “Top Music” list contains around 715 songs with around 1.9 day play time. I set the limit to at least 7 days, for this list.
After that, I tell it to limit the play list to Y items selected at random. For the “Top Music” play list, I use 75 items. I then make sure it’s Live Updating in case I add more music.
Finally, I play the list on shuffle. Since I’ve started playing my music this way, I find that I listen to all of the music in the list every month or so and I never hear a single song too often and it’s completely random.
What I really wish was that Party Shuffle would work the way I think it should. If I want to see the next 25 songs ahead, I want it to guarantee it won’t duplicate anything within that window. If I could then have it try to fit in songs I haven’t heard in a while, but prefer the higher rated songs, that would be great. It wouldn’t have to be perfect, but iTune’s play list options are abysmal.
Cheers.

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