Blame Merlin. I was listening to the MacBreak Weekly podcast and they got in to this discussion about Smart Playlists in iTunes, then Merlin Mann posted some excellent examples for using his “Music only” playlist and today some more examples for those of us with large iTunes libraries. I’ve been doing similar things with Smart Playlists for a while, so I though I should hop on the wagon and do some documenting myself. Here’s what I do with my large (~8200 songs, 40GB) iTunes Library.

Until iTunes gets grouping boolean logic, about all we serious Smart Playlisters can do is build playlists that serve as sources for other playlists. These playlists may or may not be useful on their own, but their job is to act as a positive or negative when building other playlists. Instead of a “Music Only” playlist, most of my smartlists build off of a “Stuff I normally don’t want to hear” playlist:

The “normally” is the key here. These aren’t things that I want to throw away (maybe I should throw some of them out). I’ve got a substantial Holiday collection (for the chrismahaunakwanzaa season), some nature sounds cds, and so forth. Nice, but they don’t belong in the day-to-day rotation.

Also notice that I exclude one or two stars, and if the song contains the comment “(poor quality).” I use the iTunes comment field as a tagging field. I put the tag within parentheses, so I can distinguish between tags and actual comments. So, if I rip a bad CD or download a free mp3 that is scratchy or skips or whatever, I can simply add “(poor quality)” to the comments and it’ll automatically get added to this playlist, which will (as we’ll see) zap it out of normal rotation.

My day-to-day playlist is Party Shuffle, using “Not played in 6 months” as its source. That playlist references the “Stuff I normally don’t want to hear” playlist:

That’s a pretty simple Smart Playlist, but it’s powerful. As songs get played, they’ll get pulled off the playlist and won’t appear for another 6 months. This encourages fresh music, that I’ve ranked at three stars or above.

Ratings are important to me and my playlists. You’ll notice that the “Stuff…” playlist doesn’t say “rating less than three stars” because that would not include zero stars. Zero stars (to me) doesn’t mean I like the song less than a song rated at one star — Zero stars means I haven’t given it a rating yet. So, I’ve got a playlist that I’ll put on party shuffle when I’ve got some new stuff in my Library, the “To Rate” playlist:

As you can see, this playlist also references another playlist, the “Unrated” playlist. That playlist just excludes Podcasts and stuff less than one star. While it might seem that a single playlist would suffice here, Using two, one to get everything that’s not rated, and the second to weed out the “Stuff I normally…” playlist means that I don’t have to rate the songs that won’t be a part of the normal music rotation, like all the classical and holiday music in my library.

One of the jobs that iTunes does for me is help me sleep at night. This is based on the “Sleeplist” playlist, which is not smart, but rather one that I’ve been adding music too over time, as appropriate music seeps into my normal rotation. By dragging it into the Sleeplist, it will become part of my nighttime music, and therefore get added to my “Stuff…” playlist, so it doesn’t come up during the day.

So at night I’ll switch Party Shuffle to the Sleeplist. I use a very nice piece of software called iTunes Alarm to put the machine to sleep in the early morning, so it’s not playing all night.

After doing things that way for a while, I realized that the play count for some of those songs in Sleeplist was getting really high. These were the songs that had been in Sleeplist for a long while, while the newer songs weren’t getting a high enough rotation. Not because Party Shuffle was choosing songs with a higher play count more often (at least, I don’t think so, but Party Shuffle sometimes does some interesting things with its choices) but just because of the age of the songs in the list. The solution for balancing out this? Yep, another smart playlist:

This is the “Balanced sleeplist” playlist, the one that’s now on Party shuffle at night. The play count of 100 is just an arbitrary cutoff number, but it ensures that songs that haven’t been played as much get their fair share. As songs go over the 100 cutoff, I’ll increase the number to keep a few hours of music in that list.

As I mentioned, I use the comments field to tag a lot of my music. and I’ve got several smart playlists that reference those tags. They all look pretty much the same:

This is the “Work Safe” playlist, which checks for the lack of the comment rather than its presence. I’ll add the “(nsfw)” (Not Safe For Work) tag to songs that are explicit (some time ago I asked Apple to let us use the “explicit” tag on our own music just like they do for the iTunes store and podcasts, but that hasn’t happened yet). So, as I go through the music and mark one as “(nsfw),” it’ll get taken off the Work Safe smartlist, which makes it suitable for background music when I’m working with others, or at home, and I can know that at least the lyrics shouldn’t offend.

Some of the other tags that I use are:

• (instrumental) — really nice for background music
• (live)
• (cover) — suitable for Coverville
• (mashup) and (remix)
• (from Amazon) — For a while I was keeping up with Amazon’s free music downloads, and would tag them as such

The “Top 25 Most Played” is a fun playlist, showing you really what you’re listening to. The problem that I have with it is that all of the songs in it are on my Sleeplist, which is a list containing a relatively small number of files, but plays for a couple of hours each day. Adjusting it to not include the “Stuff…” playlist reveals a much better overview of my favorite songs.

I don’t own an iPod (WHAT?!? yes, the last person in the world); my Palm T3 is my MP3 player, and I use SyncTunes to move my podcasts off of iTunes to its memory card. SyncTunes can sync from a playlist, and again I’ve used two to filter out just the podcasts that belong on the portable device. The first one picks the podcasts that I want to hear on the road. The problem is that some of those podcasts occasionally have videos in their feeds. The second playlist just picks out the stuff that isn’t Video, so only the audio files are in the playlist that SyncTunes sees.

Many of my uses would be easily solved with one playlist if iTunes would allow more complex conditions. I suppose Apple has a tough line to walk, making Smart Playlists easy enough to be accessible to the most people. Adding complex boolean conditions might clutter and over-complicate the UI for some. Until such time as they figure this out, These sorts of work-arounds will do.