My favorite radio shows on my favorite station, WMBR, mix brand new stuff I’ve never heard before, a selection of current favorites, and a smattering of catalog classics. I wanted an iTunes playlist with a similar blend. I thought what I came up with was cool enough to that it might be useful for other folks.

I like to use folders to keep things organized. Here’s my overall structure:

Because the playlists depend on one another, you need to create them in a particular order.

First, the pools are normal playlists (except for newest).

• “heavyrotation” is for the current faves, songs that I want to hear pretty often. For instance, I just went to see The Magnetic Fields, so I had several of their albums in heavy rotation to psych myself up for the shows.
• I used “queued” mostly for older music that I want to hear without frequent repeat plays. If I find myself thinking something like, “it’s been a while since I listened to The Replacements,” I’ll drag their catalog into this list.
• “newest” is a smart playlist itself. It’s similar to the default smart playlist “Recently Added.” I use a shorter timeframe, since I have a pretty steady stream of new music coming in.
  
  I don’t currently have any non-music in my iTunes, but I future-proofed my rule to exclude videos or e-Books in case I ever do, and to make it easier for other folks to adopt and adapt my filter rules.

When I start to get tired of hearing The Magnetic Fields all the time or when all my favorite Replacements songs have come up, I can just delete those artists/albums from “heavyrotation” and “queued.” (I can also sort those playlist by the playcount and ditch the songs I’ve heard most). “newest” cleans itself up automatically to keep things fresh.

Next, the metafilters are smart playlists that filter the pools. I don’t usually listen to these playlists; instead they are used to create the metalists that I actually listen to. These lists manage how often tracks come up in shuffle mode.

• _heavyrotation
  
  The source “heavyrotation” consists of tracks I want to hear a lot of, so the same track can come up multiple times in a single day. But I figure if I skip it once today, I’m not in the mood, so it won’t come up again the same day.
• _queued
  
  The source “queued” consists of tracks I want to hear somewhat less of, so the same track can only come up once a week. Again, I figure if I skip it once today, I’m not in the mood, so it won’t come up again the same day.
• _newest
  
  The “newest” source has a slightly different focus. I try to listen to everything through at least once, so I can make sure CDs/downloads aren’t glitchy, and form an initial impression. If something catches my ear, I can add it to the “queued” or “heavyrotation” lists, so the newest list is set to never repeat. The skip rules are a little different; if I skip it several days in a row I must dislike it, but generally I want to give everything a chance.

Finally, the metalists combine the metafilters to make the playlists for listening.

• “New, Q’d & Heavy” is the main playlist, it combines all three of the metafilter lists.
  
  I uncheck items to indicate things that I don’t want to ever come up in shuffle play, so I reflect that in the overall rule.
• If I’m not in the mood to hear new music just now (e.g., I want some background but I’m not paying enough attention to evaluate new material), “Q’d & Heavy” does the trick:
  
• If I want a little break from those songs I hear all the time, “New & Q’d” is the ticket:
  
  (I wish I could flip a software switch like this for real radio stations!)

A few additional notes:

• Everything is set to “Live updating,” so if you purchase downloads or digitize from a CD, the tracks show up in all the playlists immediately. If you’re listening in shuffle mode, though, the shuffle order is only set when you re-start the playlist — otherwise, new tracks are just added to the end of the shuffle order. So, for example, if you’re listening to “New & Q’d,” you need to click on some other playlist (so iTunes shows you a stop button instead of a pause button), stop the “New & Q’d” list, click back to it, and start it again to make it reshuffle with the new tracks included.
• For the geekier component of the reading audience: the “secret sauce” is that using a smart playlist as the source for another smart playlist lets you mix AND filtering with OR filtering, which you can’t do in the rules for a single list.
• There’s plenty of room for improvement. I’d love for the _heavyrotation metafilter to do something like only play a track once in 6 hours, or no more than twice a day. I haven’t figured out a way to do that (I’m not sure it’s possible). I’d also love to come up with a way to weight things, so, for example, new tracks would be twice as likely as anything else. Suggestions welcome!

This is on the home iTunes. I keep my iTunes music on external hard drives; the one at work has the same content, but different play counts. I’m about to go to a 4 hard drive model with classical/jazz on different drives, because the danged drives are almost full.

Total length: 70:08:08:26 (28095 songs)
I gotta say, including things-smaller-than-seconds is a confusing default degree of precision. I had resort to a calculator to check the order-of-magnitude. 30,0000 3-minute songs would only take 62.5 days to listen to, not 62 weeks, months, or years.

First and last songs (by title):

• ‘A’ Bomb in Wardour Street – The Jam
• . } @ } . @ . } @ } . @ . } @ } . @ . } @ } . @ . } @ } . – The User
  but I prefer to sort numbers and punctuation first, not last, so:
  Zewi streifen im Blau – Couch

Sort by time – shortest and longest:
2 real tracks tied at 4 seconds:

• Six at 9 – The Blue Up?
• Gooseneck Problem – Yo La Tengo

If I don’t count single-track live broadcasts:

• Like Silver Like Song (continuous version) – Jane Ira Bloom (61:25)

If I don’t count single-track albums:

• H. Sidakr of Loops – The Blue Up? (34:10)

If I don’t count a single “bonus” track that’s the rest of an album reversed:

• Radio – Amatoroj – Sonic Youth

runners up:

• Oahu – The 6ths (28:10)
• Sunsquashed – Yo La Tengo (26:21)

Sort by Album – first and last:

• A-OK – Flin Flon
• 9 Love Songs – The Marknetic Fields
  or by a reasonable sort criterion
  Zopilot Machine – The Mountain Goats

Sort by Artist – first and last:

• The A-Lines
• +/-
  or
  Zsammy

Top five played songs:

1. It’s All Been Downhill Since the Talkies Started to Sing – Hallelujah the Hills
2. The Icecaps of Mars (Are Just Copying Ours) – The Capstan Shafts
3. Cashout – Fugazi
4. To All My Scientist Colleagues I Bid You Farewell – Hallelujah the Hills
5. Daddy Told Me – Pristine

Find the following words. How many songs show up?

• Sex: 189
• Death: 287
• Love: 1230
• You: 3061
• Home: 212
• Boy: 427
• Girl: 570

First five songs that come up on Party Shuffle:

1. Stylized Ampersand – Unrest
2. Twenty Second/Sundial – Friction
3. I Don’t Care If You Go – Velocity Girl
4. Marooned – Wire
5. Denial – Tuuli