DRM is a headache which limits where you can play your songs and how many often can you play them. Here is one way to hack through the encryption and perhaps legally with iTunes.
- Create a separate new playlist with all the songs you’d like to rip.
- Use your software’s Burn Disc option to copy the music to audio-CD format.
- Now, rename the original playlist to save your original songs.
- Insert the newly burned Audio-CD and import to copy the songs back to iTunes.
You should get your DRM free songs now.
Disclaimer: I have not tried this myself and have not come across a situation where I’ve to do it yet.