I love playlists. I have 79 of them on my iPod, and devote the same kind of care to them that I once poured into party tapes. Yet I keep thinking, there’s a better way to thread one’s way through a music collection, creates a greater degree of surprise for the listener, yet still reflects their preferences and capitalizes on the idiosyncratic associations that we all develop between songs.

Rather than listening to playlists, which are a metaphor from radio broadcasting, why not do with music what we can do with electronic texts? Why not enable a kind of listening that isn’t fixed and linear, but is still purposive and intentional? In other words, you should be able to create hyperlinks between songs, not just arrange them in a fixed order.

Start with, say, Halo’s “Halcyon.” On my playlist, I’ve got it between a song from the “My Neighbor Totoro” soundtrack and Mogwai’s “Two Rights Make One Wrong,” but it would also fit well in a playlist with Pink Floyd’s “Comfortably Numb;” Neil Young’s “Cortez the Killer” (it’s that combination of ringing guitars and sad melody); or Steve Reich’s “Different Trains.” Each of those songs, in turn, has its own associations for me; and those songs have their associations.

Likewise, Sting’s “Stolen Car” fits well between Seal’s “Prayer for the Dying” and Blue Nile’s “Headlights on the Parade,” but also would sound good with U2’s “Ultraviolet,” Bryan Ferry’s “Slave to Love,” or Starfish’s “Under the Milky Way”–

–which in turn which works with Midnight Oil’s “Beds are Burning,” Tears for Fears’ “Woman in Chains,” or K. D. Lang’s “Constant Craving,” which I put in the same mental category as Nina Simone’s “I Shall Be Released” (which in turn links to Dylan’s version), Jessica Andrews’ “Now,” and Fiona Apple’s “Criminal.” And on and on, marching through one’s hard drive.

An iPod that followed the paths I set (this song links to these other songs), and could throw in some songs based on categories I choose (include songs from the same album, or songs from bands that an artist was previously in, or songs that came out the same year), would be a formidable piece of entertainment technology.