The best way to get a playlist onto an iPod or iPhone

It’s my firm belief that the bloated, horrible software that is iTunes will ultimately be the downfall of Apple’s music business. It’s really, really awful on a variety of fronts (performance, openness to outside developers, etc.), but is sadly the most reliable way I can get music onto my iPhone and iPod. Beyond that, I try to stay out of iTunes as much as possible.

While the Windows Media Player 12 (part of Windows 7) has improved significantly over the previous version, particularly in terms of performance and streaming more video formats out of the box, as a simple jukebox it still leaves a lot to be desired. The best media player app I’ve found is Songbird, due to several factors such as a) it’s open-source, b) it has a number of great community-built plugins for things like lyrics, and c) it allows you to manage your music in ways the other apps simply cannot.

A simple example is “What is the best way to get a playlist onto my iPod/iPhone”? This is much more complicated than it should be if you have a large library (i.e., too large to handle in iTunes, which isn’t much). So the best way is to create it in Songbird, then export it into a PLS file that can be read by iTunes. So the steps are

  1. Install Songbird.
  2. Install the “Playlist Export Tool” add-in. I suggest also installing the Windows Media Playback and LyricMaster add-ins while you’re at it.
  3. Import your library into Songbird by following the directions.
  4. Make the playlist you want. The search box in the upper right can be really useful in this.
  5. When done go to File->Export Playlist(s)
  6. Check the playlist, then click “Done” to save it as a PLS to the specified location.
  7. Close Songbird and open iTunes. You can now drag the PLS file into iTunes, which will then import the songs it needs. You can then sync it with your device.

This way you can actual spend time listening to your music, not fighting with iTunes.

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