I love my Archos Gmini 220. It doesn't play movies, make phone calls, or take snapshots, but it provides me 20GB of digital music and files that I can take anywhere and transfer to any computer. It also only cost me $150 two years ago and is still going strong (with the help of one critical rubber band). It's also very solid as a lo-fi recording device for live shows.
While I don't need a portable music player that massages my back or sorts my laundry, I do need one that can shuffle my tracks randomly. Unfortunately, like most portable media players, my Gmini fails miserably. While shuffling, it will often play the exact same string of songs I heard just a few hours earlier.
So what's a variety-loving listener to do? Well, I make playlists, usually "smart" playlists in MediaMonkey using the "last played" criteria. Of course, Apple's iTunes also provides similar functionality, as do a number of other free digital-music jukeboxes.
Those looking for more automation in the process should check out The Filter, a plug-in for iTunes that will automatically create intelligent playlists based on your own preferences. I've had mixed results, but Peter Gabriel supposedly swears by it.
The future of random playlists will likely happen on the Web. A number of Web sites like imeem and FineTune let you create your own mixes for embedding on your blog or home page, but they haven't yet taken the leap onto portable devices.
When you're looking for a mix of various songs, do you leave your listening choices up to the God of Shuffle, or do you use software or Web sites to help you build playlists? Tell me about your own secret tricks for great mixes in the comments.