Sometime between January 27th and October 30th, I thought this stuff was interesting. You might think so too!

While there’s been some grousing about the accuracy of iTunes 8’s new Genius feature, I’m getting a kick out of playing with it. Sure, it’s not always spot-on (though Apple says that will change over time as their database grows and the matching AI improves), but that lends a certain entertainment value to the playlists it generates. When it works, though, it’s slick.

Here’s a playlist my iPod just put together (pulling only from songs that happened to be loaded at the time), seeding off of Tony Bennett’s take on “Steppin’ Out With My Baby”:

  1. Tony Bennett, “Steppin’ Out With My Baby”
  2. Frank Sinatra, “Nice ‘n’ Easy”
  3. Bobby Darin, “More”
  4. Johnny Mathis, “Chances Are”
  5. Dean Martin, “You Belong to Me”
  6. Fred Astaire, “The Way You Look Tonight”
  7. The Andrews Sisters, “Boogie Woogie Bugle Boy”
  8. Marilyn Monroe, “Diamonds Are A Girl’s Best Friend”
  9. Billie Holiday, “All of Me”
  10. Perry Como, “Magic Moments”
  11. Louis Armstrong, “West End Blues”
  12. Louis Jordan, “Let the Good Times Roll”
  13. Benny Goodman, “Swingtime in the Rockies”
  14. Frank Sinatra, “Witchcraft”
  15. The Glenn Miller Orchestra, “At Last”
  16. Bobby Darin, “Hello, Dolly!”
  17. Billie Holiday, “Spreadin’ Rhythm Around (Remix)”
  18. Tony Bennett, “(I Left My Heart In) San Francisco”
  19. Dean Martin, “That’s Amore”
  20. Louis Armstrong, “Ain’t Misbehavin'”
  21. Duke Ellington, “Take the A-Train”
  22. Judy Garland, “The Man That Got Away”
  23. The Andrews Sisters, “Rum and Coca-Cola”
  24. Billie Holiday, “God Bless the Child”
  25. Frank Sinatra, “You Make Me Feel So Young”

Not bad at all, I’d say.

(I also love that I just happened to have the songs on my iPod to build that kind of playlist. It’s semi-randomly loaded, so there’s often no real telling what might be on there at any given time. Hmmm…it may be about time to do another “here’s how I organize my music” post….)

iTunes FoldersAnother meme that Kottke pointed out — iTunes usage methods.

How you organize your music can be as important to someone as what music they listen to. For me, with a personal CD collection currently somewhere around 1,200 discs, organization becomes extremely important. Luckly, iTunes has everything I need in order to keep track of what I have, find things easily, and discover music I hadn’t heard in a while (and at times, didn’t remember that I even had).

One of the godsends of iTunes is the “smart playlists” feature — I use smart playlists almost exclusively (they’re the purple-colored icons in the screenshot). Essentially, a smart playlist allows you to set certain criteria that determine what songs are in the playlist, which is then automatically updated by iTunes. For instance, I keep three smart playlists synced to my iPod at all times: “new additions”, “random unplayed”, and “random 1gb”.

  • Random 1Gb: the single most important playlist, for me. This randomly grabs one gigabyte’s worth of music that 1) I haven’t listened to in the past 2 months, 2) is rated three stars or above, and 3) isn’t in the “Christmas” genre. Whenever I listen to a song, it removes it from the playlist, and grabs another one. This syncs with my iPod, and as the iPod tracks what I listen to each day, the playlist is automatically updated at night when I get home from work, and in the morning just before I leave. The end result — roughly 20 hours of songs that I know I like, but haven’t heard in a few months.

  • Random Unplayed: this playlist grabs one gigabyte’s worth of music that I’ve never listened to. This comes in handy when I’m importing a lot of music (like now, as I re-import all 1200 CDs to AAC rather than .mp3) — as long as there’s something in this playlist, then I know that there’s songs that I haven’t listened to yet (either just to listen, or to check to ensure that the rip was completed successfully).

  • New Additions: this is, quite simply, any songs that have been added to my library within the last two weeks. Great for being able to explore a new album right after buying it.

Other smart playlists that come in handy: “recently played” (anything I’ve listened to in the past two weeks, handy for tracking down something I know I heard recently), “top 25 played” (a pesudo-best-of list), “top rated” (any songs rated four or five stars), and the various by-year playlists (listening by era can be quite interesting sometimes).

The only two “normal” playlists I have at the moment are one for Poems for Laila (from when I was making CDs for Prairie last weekend), and one for Sony’s excellent Soundtrack for a Century collection. Other than those two, it’s all smart playlists for me.