From Salling Software:
Salling Media Sync synchronizes playlists, music, and podcasts from iTunes onto your mobile phone. It's free to use, but when registered it intelligently updates your phone, which is much faster. The application couldn't be easier to use. Once the phone is connected to a USB port, simply select the playlists and podcasts you want on the device. Salling Media Sync not only uploads the music tracks and podcast episodes, but also replicates each actual playlist on the device and--on devices that support it--transfers play count metadata for each item to the device, reinforcing the sense of having a piece of iTunes in your pocket. Although Salling Media Sync works miracles with most media in iTunes, it can't bring over DRM-protected content. Please visit http://www.salling.com/MediaSync/Mac/ for an up-to-date list of supported devices.