A:Answer Yes, you can. I do it all the time. I create a Playlist in iTunes, and then copy all the songs and paste them to the SportClip PLus MP3 player. I have an old laptop that is not very fast, so sometimes, I have to only copy/paste a small segment of the songs at once (like a block 010-20 songs) and it works fine. If you have a faster laptop, you should be able to copy and paste a large block of songs to the SportClip player easily. I have been doing this for years. Enjoy your SportClip! I love mine and it has been essential in motivating me during my gym workouts, for three years now.