iPod & iTunes: Shuffling for Experts
Life is random - that is Apple's motto for the new iPod shuffle. While the Autofill feature sounds nice, us control freaks want to build our own, wonderful random playlist. But not quite so random. iTunes' Smart Playlist allow for great control but the setup is not really trivial.
Something old, something new...
Personally I do not like to listen to completely random playlists. Like a good radio station I prefer to hear a mix of favorites, some stuff I haven't heard in a while and the occasional strange track I wasn't expecting. The tracks I bought last week on the iTunes Music Store need to be in there as well. For the great mix, try the following:
Rate your music!
Do this anyway. Whenever you use smart playlists your rating will help give you a basic filter. What schema exactly you use to rate your songs is up to you.
Blacklist
Make a manual playlist. Call it "Don't shuffle". Put all the tracks in there you do not want to hear when shuffling. I put Audio Books, Childrens Songs, Holiday Songs and most Soundtracks in there. Using a manual playlist makes this easy to update. if you ever encounter a song you don't want shuffled, just drag it in there.
Favorites
Make a new smart playlist. The sole criterium should be "|Rating| |is greater than|" and choose a rating threshold that is comfortable for your ratings. Then check next to "Limit to |100| |songs| selected by |highest rating|." Call this playlist "Favorites".

Most Played
Make another new smart playlist. Deselect "Match the following condition" but then check next to "Limit to |100| |songs| selected by |most often played|". This is your personal all time billboard chart. Call this playlist "Most Played"

Long time no hear...
Create another smart playlist. Set the first criterium to "|My Rating| |is greater than| |(no stars)|". Then add a another criteria: "|Last Played| |is not in the last| |3| |months|". Check next to "Limit to |100| |songs| selected by |least recently played|". Call this playlist "Rare".

Hot stuff
Create another smart playlist. (Will this never end?) Set the first criterium to "|My Rating| |is greater than| |(no stars)|". Add another criteria: "|Date added| |is in the last| |3| |months|". Call this playlist "New".

Spice
One more smart playlist. Set the one criterium to "|Playlist| |is not| |Don't Shuffle|". Then check next to "Limit to |75| |songs| selected by |random|". This will be a list with completely random songs, just to spice things up. Call this playlist "Completely Random".

Whitelist
Create a smart playlist. (We will be there soon.) Add the following criteria:
- "|Playlist| |is| |Favorites|"
- "|Playlist| |is| |Most Played|"
- "|Playlist| |is| |Rare|"
- "|Playlist| |is| |New|"
- "|Playlist| |is| |Completely Random|"
Select "any" in the first line, so it reads "Match |any| of the following conditions." Call this playlist "Do Shuffle."

Bringing it all together
Create a (last) playlist. Make two conditions:
- "|Playlist| |is| |Do Shuffle|"
- "|Playlist| |is not| |Don't Shuffle|"
- "|Last Played| |is not in the last| |2| |days|"
The first line should read "Match |all| of the following conditions". Then check next to "Limit to |xx| |MB| selected by |random|". Call this playlist "Expert Shuffle". This will combine the songs you want (Do shuffle) and exclude those you do not want. (Don't shuffle)

The last condition will make sure, you do not hear the same songs over and over and lead to some additional randomness. The time interval you choose here should be longer than the average interval in which you connect your iPod to your computer. The size you limit this playlist to, should be the size of your iPod, minus the amount you use in disk mode. For the larger iPod you can of course build a smaller expert shuffle in addition to other playlists.
You will probably have to adjust the parameters in these playlists. If you have a rather small or rather large iTunes Library you will want to adjust the limits for the smart playlists. If you adjust the limits differently the weighting of the different playlist changes.
While you enjoy your expert shuffle there are some other ideas:
Use the Skip button
If I had designed the iPod Shuffle I would have made the skip button at least as big as the play button. Shuffling is great and fun, but no matter how good your playlist is, there will be this occasional song that doesn't fit your mood. Skip it. Eventually the song will drop out of most smart playlists and not come back.
Update your ratings
Eventually your taste will change and the song you loved to hear last season bores you now to no end. Update your Ratings accordingly. Remember to add ratings to new song so they appear immediately.
Flavors
You can add different flavors of the Expert Shuffle by making more playlists with additional conditions, such as "|Genre| |is| |Rock|" and the you have a shuffle with only Rock songs.
Smarter non-shuffling
You can also make the "Don't shuffle" list smart, automatically filtering certain genres and maybe the encoding (don't move the large ALE and aiff files to the iPod shuffle). You can also combine the automatic "Don't shuffle" list with a manual one.
Reshuffling
You can update smart playlist by selecting all (or certain) tracks and deleting them. iTunes will then refill the smart playlist with other tracks that match its conditions. Here, there are actually two playlists that need to be refreshed.
Only updating the "Expert Shuffle" playlist seems fine but it is based (among others) on the "Completely Random" playlist and unless you are happy with the same completely random subset of songs all the time, you want to refresh that occasionally as well.
However updating two playlists is tedious, so we need a script... ;)
Refresh Expert Shuffle
Click on the link, save the script. If you are using the Script Menu, save the Script in ~/Library/Scripts/Applications/iTunes/. If not, you can add a iTunes specific Script menu item by creating a folder called Scripts in ~/Library/iTunes/ and save the script there. (Restart iTunes to see the menu.)
This Expert Shuffle list should be seen as a starting point. Play around with the parameters and adapt new ideas to fit your mood. Smart playlist are an extremely powerful tool to filter your music, but they do need a little thought and planning to use their full potential. Most of all: Have Fun!
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