Smart playlists are the sole reason for my iTunes loyalty. I stick with the software through each and every frustrating, bloated update because I've yet to find another music player that can match the fine-tuning of smart playlists that's possible in iTunes.

Thorin Klosowski shared some tips the other day for using smart playlists to organize your music library. Some good ideas, but they only scratch the surface. Over the past several years I've developed a system for getting the most out of a large music collection.

The key breakthrough for me came a few years ago when I realized you could group smart playlists into folders, combining several tiny smart playlists into one large, complex one. The result is an diverse, decade-spanning, constantly refreshed playlist that serves up my favorite tracks most often but also grabs forgotten gems that I haven't heard lately.

Taking iTunes Smart Playlists To The Next Level of Music Nerdery

Step one is to create a playlist folder. I named mine *The System* (the asterisk bumps it to the top of the alphabetical listing in the playlists sidebar).

Next, you begin populating your folder with micro-playlists. Most of mine have between three and five songs each. You can calibrate each one later based on the type of music you want to hear most.

I have three types of smart playlists in my folder.

1.) Five-Star Songs. I reserve five-star ratings for about 40 to 50 current songs that are my "heavy rotation" at any moment. When I buy a new single that I want to hear a lot, I mark it five stars. When I get sick of hearing it, I drop it down to four stars.

Taking iTunes Smart Playlists To The Next Level of Music Nerdery

2.) Year-Based Playlists. I created a series of smart playlists by decade or half-decade. After setting the year range, I limit the playlist to songs that have not been played in the last 18 months. (I have a large music collection. You might want to calibrate your playlist to 6 or 12 months, depending on the size of your collection and how often you listen to it.)

Finally, I limit the playlist to a handful of songs, selected randomly. The result is that as soon as iTunes gets done playing Eddy Grant's "Electric Avenue" (1982), it drops off of my 1980s playlist for at least 18 months, making room for, say, The Pixies, "Here Comes Your Man" (1989).

Taking iTunes Smart Playlists To The Next Level of Music Nerdery

3.) Most-Played Playlists. My latest addition is a set of three play-count-based smart playlists. Maybe I'd like to hear "Electric Avenue" more often than once every 18 months. I've listened to it 59 times in iTunes, making it one of my 100 most-played songs. These most-played playlists cycle in my 100, 500, and 1,000 most-played songs more frequently than the rest of my collection.

Creating these lists are a two-step process. First, you need to create three smart playlists somewhere *outside* of the folder you created for your micro-playlists. Start each one with the rule "Media Kind" "is" "Music." Then limit them to 100, 500 or 1,000 songs, selected by "most often played." I titled my lists "Top 100," "Top 500," and "Top 1,000." Here's what one looks like:

Taking iTunes Smart Playlists To The Next Level of Music Nerdery

Next, go back to your smart-playlists folder and create three more smart playlists with two rules each. The first is "Playlist" "is" "Top 100" (matching the name of your 100 most-played playlist you just created). Then I create a "Last Played" rule that's something less than the 18 months I use for my year-based playlists. I use two months for my Top 100, four months for my top 500 and six months for my Top 1,000. You can calibrate based on your use and preference. I also randomly limit each list to somewhere between five and ten songs.

Taking iTunes Smart Playlists To The Next Level of Music Nerdery

And now, sit back and enjoy your music library! Click on your playlist folder, then choose random shuffle. You'll get a mix of your favorite songs of the moment, mixed with your old favorites, and sprinkled with an eclectic mix of the rest of your collection.

Taking iTunes Smart Playlists To The Next Level of Music Nerdery