Thrupp makes it stupidly easy to get albums from your iTunes library to your MP3 player or phone. Drag music from iTunes to the Thrupp window to copy it to your player.

Features:

Easy Copying
Thrupp makes copying music from your iTunes library to a player or memory card completely automatic. Just tell it what music you want, and Thrupp does the messing about with files for you. And configuration is easy too - Thrupp comes with presets for popular phones and devices.

Flexible Management
Thrupp doesn't limit you to storing one playlist on your player. Thrupp allows multiple playlists, each in their own folder. You can also copy whole albums separately without making a playlist.

Continuous Updating
Edit a playlist within iTunes and within seconds Thrupp will start copying and rearranging your files. It even works for Smart Playlists

Play Any Format Anywhere
By default, iTunes imports CDs as AAC files, which can't be played on most portable players. Thrupp will convert them to ordinary MP3 files that you can play anywhere. In fact, your player can now play anything iTunes can (excludes iTMS purchases). And your library remains untouched.

More Music
Imported your CDs at a high bitrate? Thrupp can convert your songs to a bitrate more appropriate for your player, resulting in smaller files and more music. And don't worry, it won't mess up the high quality versions in your library.

Multi-threaded
Finally, the best thing about Thrupp is that it doesn't leave you staring at a progress bar or a spinning cursor while it updates your player. Adding, removing and converting songs all happens in the background, leaving you free to browse your library and add or remove more songs.

Thrupp is compatible with all phones, players and memory cards that can appear as drives in the Finder and do not require special software.

Requirements:
OS X 10.3.9 -10.5
Universal Binary