I love MediaMonkey‘s AutoPlaylist option that dynamically scans your library based on user-set filters and creates a playlist for your listening pleasure. Here are a few I’ve set up that I love going to when I don’t quite know what I want to listen to:

• ADD Playlist: Under 30 minutes – Follows the ADDreviews model. Creates a random playlist of 30 tracks under a minute long each.
• College – All tracks recorded between 1994 and 1998. (Similarly, “High School” has tracks from 1990-1994.)
• Favorite Polish Tracks – Any tracks in my “Poland” directory that I’ve rated 4 stars or higher.
• Jazz in Under 5 – Random jazz tracks that clock in at under five minutes.
• Hip-Hop By Year – 20 random hip-hop tracks that I’ve rated 3.5 stars or higher, sorted by year. Serves as a brief history of personal hip-hop favorites. Just made this one today and I’m loving it. (I also have one of these that’s the same idea, except with 700 megs of tracks for an MP3 CD’s worth.)

A few years ago, I had a pretty sparse collection of music digitized and was still listening primarily from CD. These days, though, I’ve really adapted to listening to music differently. I still usually listen to entire albums rather than relying on some sort of random selection, but every so often, I like the option to listen to random tracks by year, rating, genre, or some combination thereof.