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Was browsing around this site, very happy to see other people are as crazy as I am about playlists. Nothing I saw really came up with something I felt really happy with. I configure my iPod/iTunes a little weird. I have over 120GBs of MP3s and a 20 GB iPod. As I am very shady about iTunes messing with my tags, I actually have all my music for my iPod set aside just for iTunes. Also, I'm a stringent album-only listener. I never listen to random music, but my iPod got me rating songs and now I have over 530 rated tracks on my iPod that I can listen to randomly, but no playlist would give me enough slack to hear what I wanted to while still hearing stuff I haven't listened to in a while.
I tried doing playlists divided up by time period, tracks not listened to in a week, etc, but this got tiring after a while. You end up listing to the whole playlist and then moving on to 3 Weeks, or This Week, in which you end up listening solely to music you've already heard, or music you probably don't want to hear. So, instead, I came up with this once I discovered the "Playlist Is" function. It's composed of multiple playlists that all feed in to each other to achieve a list that is truly semi-random. (The P:'s are how I organize my list, included for sorting purposes.)
All playlists have the following options in addition to stated options.
Match Only Checked
Live Updating
P:LRP
Limit to 50 songs selected by least recently played
P:LP
Match All
My Rating is greater than 2
Playlist is not P:LRP
Limit to 50 songs selected by least often played
P:MRP
Match All
My Rating is greater than 2
Limit to 50 songs selected by most recently played
P:MP
Match All
My Rating is greater than 2
Playlist is not P:MRP
Limit to 50 songs selected by most often played
P:Random
Match All
My Rating is greater than 2
Playlist is not P:LP
Playlist is not P:LRP
Playlist is not P:MP
Playlist is not P:MRP
Limit to 50 songs selected by Random
Then all these playlists feed into the following lists.
1:Shuffle
Match All
Playlist is 2:Shuffle All
Last Played is not in the last 4 days
2:Shuffle All
Match All
Playlist is P:LP
Playlist is P:LRP
Playlist is P:MP
Playlist is P:MRP
Playlist is P:Random
And just to mix things up even more, I include:
3:Middle Ground
Match All
My Rating is greater than 2
Playlist is not P:MRP
Playlist is not P:MP
Playlist is not P:LP
Playlist is not P:LRP
Limit to 80 songs selected by random
1:Shuffle is the primary playlist you listen to regularly. 2:Shuffle All is the main playlist that is composed of all the others, that you can use to branch off more complex time-based playlists.
The idea, and it might be flawed, is to keep a going cycle of music you haven't listened to recently, music you like, and some random stuff thrown in from your collection. You can adjust the "limit to" numbers yourself, like I can already tell I might want to decrease the number of "most recently played" tracks. Etc, it's all highly customizable.
Been listening to it for an hour now and it keeps playing good stuff, so I'm happy. Hope it helps someone out.
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I had to change the "Match All" setting to "Match Any" in the '2:Shuffle All' playlist in order to see any tracks at all. The 5 playlists being sources by 2:Shuffle All are mutually exclusive of each other so "match all" creates an empty list.