iTunesI have just about 9,000 songs (35GB) in my iTunes library, and I listen to music the entire time I’m in the office every day. I live and die by my smart playlists. I’ve seen more than a few tutorials lately about how to utilize this iTunes feature, so I thought I’d toss my hat in the ring with a few tips on how to make Apple’s killer app work better. Here are five tips to keeping your daily listening enjoyable.

5Update Your Genres!

This is a key first step in keeping your music organized, and keeping your music organized is the best way to get to hear what makes you happy. I am a bit of a freak: I have been meticulously categorizing and detailing every mp3 added to my collection for almost a decade now. I love music, but I don’t, for example, have a single song by The Beatles or Tom Petty and the Heartbreakers. I do have 212 songs by Beatles, The and 111 songs by Petty, Tom and the Heartbreakers, though.

This is a key first step in keeping your music organized.

I’m not saying that you have to go that out of control with your music library, but you can certainly take the time to properly tag your genres. If you’ve got over 400 Christmas songs on your computer you’re going to start getting annoyed pretty quickly when “Winter Wonderland” starts playing in July. The folks at Apple configured iTunes with a dozen or so default genres, and it’s beyond simple to select a bunch, right-click, and batch update the genres on them. At the very least you should separate Country, Holiday, Rock, and Rap! Once you’ve set the genres on your library you’ll find that creating smart playlists becomes infinitely easier.

4Rate Those Songs!

If you want to have a playlist based on your favorite songs, you’re going to have to start rating them. Yes, you could create a “regular” (i.e. non-smart) playlist and drag and drop just the tracks you really like into it, but that’s going to get old in a hurry. When you’re using your iPod it only takes a second to click that middle dot a few times and update the rating of a song. Surely “Yesterday” should get five stars, even if you don’t bother with updating the rating on those 33 White Zombie mp3s you grabbed from your buddy’s fileserver.

It only takes a second to click that middle dot a few times.

To make it easier for me to stay on top of my ratings, I have a smart playlist called “Unrated”. This works best when you’re using your iPod and not listening on your computer with iTunes. (The problem is that if you create a smart playlist and tell it to only include songs with no rating, as soon as you rate one while you’re listening, it disappears from the playlist and you come to a screeching halt.) My “Unrated” playlist is set to include songs where My rating is [no stars] and limit to 25 items selected by most often played. If you build a smart playlist like this, what do you get? Well since you’re selecting on most often played these should be songs that you know what to rate pretty quickly. If you’ve heard “Hit Me, Baby, One More Time” more than 30 times you know it’s a four- or five-star tune, right? (C’mon. This is your personal rating on your personal collection. Don’t let peer pressure keep you from giving Brit the props she deserves.) Sometimes I will change this to sort by most recently played instead; if I’ve heard it recently I’m more likely to have an opinion on it.

Rating your songs gives you the ability to create “favorite” playlists. If you’re keeping your genres updated then you can create a playlist for wrapping presents (Holiday, My Rating is greater than 3 stars), for being stuck on the highway (Hard Rock, My Rating is greater than 3 stars), or lame dinner parties (Soft Rock, My rating is less than 3 stars).

3Separate the Slow Stuff!

This is one of my most important rules. The vast majority of the time I am not in the mood to hear slow songs. I’m running a company here, man. I need to hear rock and roll. Hip hop. The 1812 Overture. Although I love both versions equally, I do not want to hear Linda Ronstadt or Roy Orbison start crooning “Blue Bayou” while I’m in the middle of pumping out code or designing a user interface. The best way to keep most Norah Jones tracks out of your smart playlists is by creating a “dumb” playlist.

The vast majority of the time I am not in the mood to hear slow songs.

Just click “File” and then “New Playlist”. Title it “Slow Songs”. Any time you’re jamming away and Barry Manilow starts crying for Mandy, right-click him and choose “Add to Playlist » Slow Songs”. Then when you make smart playlists, you just have to add a restriction of Playlist is not Slow Songs.

2Cycle Your Songs!

Most of the time I’m listening to one of three playlists while I’m at the office. “Daily Listening”, “Listen to This”, or “New Sh*t”. Each of these has a specific purpose and I’ll flip between them throughout the day.

  1. Daily Listening
    This one’s pretty simple. Give me everything where the genre isn’t Holiday, Speech (to avoid hearing JFK’s Inaugural Address in the middle of the afternoon), or Country. Make sure it’s not a video or a podcast and that it doesn’t have one or two stars. Of course don’t include anything in the “Slow Songs” playlist, and limit it to the 25 items that I’ve heard least recently. (I say not to include one- or two- star songs because I don’t want to hear music I’ve explicitly tagged as crap, but I can’t just say where my rating is greater than two stars because then it won’t include the hundreds of songs that I haven’t rated yet. Get it?)
  2. Listen to This
    Smart PlaylistsHere’s another easy one. Exclude the same genres and the slow songs as in the above playlist, but only give me songs where the rating is greater than three stars. The trick here is to limit the songs based on least recently played. Sometimes I’ll listen to my four- or five-star playlist because I’m just in the mood to hear my favorite music. The “Listen to This” playlist will grab me those favorites that I haven’t heard in a while. (Has it really been three months since I heard the Violent Femmes‘ “Kiss Off”?!)
  3. New Sh*t
    I am constantly adding new music to my library. I keep one playlist like this just so that I can hear the new songs. Again I’m excluding those pesky moment-related genres and the slow stuff, and I have the one- and two-star exclusion on just about all my smart playlists. The “New Sh*t” playlist has a parameter for Date Added “is in the last” 3 months, and another parameter to make sure Last Played “is not in the last” 1 day. That way I won’t get sick of Sugarcult‘s awesome new “Los Angeles” by hearing it fifteen times in one late night of programming.
    I alternate the limit clause on this playlist. Sometimes I have it set to “least often played” and sometimes I have it set to “least recently played”. The Date Added parameter makes sure that the songs are still new; I just vary the limit to keep it fresh.

1The Hidden Secret: Groupings!

Most people don’t have any idea what the Grouping option is in iTunes. I actually can’t say that I know what Apple was thinking either, to tell you the truth. But I can tell you how I use it. Grouping is a text field; you can type whatever you want in that box. I use it to “tag” my music. If you start tagging your songs you can create even more specific smart playlists based on your tags. Here’s an example: “Suicide Blonde” by INXS is in the “Rock” genre. It’s not “Dance” and it’s not “90s” and it’s not “Alternative”. It’s good old Rock. You shouldn’t incorrectly change the genre just to categorize something. So what can I do? I can tag it with an identifier that I like. This one gets the tag “701″. (701 South was a club in Daytona Beach where I went to high school.) Then I can create a smart playlist to give me any songs where Grouping contains 701 and I can pretend I’m 17 and drinkin’ on a fake ID again.

If you start tagging your songs you can create even more specific smart playlists based on your tags.

What’s cool about the Grouping option is that you can include multiple items in that box. So “Suicide Blonde” gets tagged like this: .701.daytona.highschool.party. Now I can create smart playlists based on any one of those tags!
Note that I wrap each tag with a period, including the first and last tags. That way I can have multi-word tags and also it lets my smart playlists tell the difference between a song tagged with “LA” and one tagged with “lame”.

Wrap It Up

So there you go. Smart playlists are a powerful way to organize your music and keep you listening to what you want. I hope these tips help you, because you can’t just live your life on shuffle all the time.

03/04/09 Update: I now have 10,738 songs (about 43 GB) in iTunes.

12/14/09 Update: I now have 11,296 songs (about 46 GB) in iTunes.

Update 03/20/2012: I now have 13,293 tracks (60GB) in my iTunes library and still utilize all of the tips mentioned here.