Another amazing comic by xkcd:

I spent more time trying to get an audible.com audio book playing than it took to listen to the book. I have lost every other piece of DRM-locked music I have paid for.
I fully agree with this comic. Fighting with DRM is a nightmare. I gave up on itunes for this very reason and I am unlikely to go back until the remove all DRM and starts using public licenses.
Note: James legal point xkcd Understates the Case for Piracy
Garden-variety downloading opens you up to civil liability, but it doesn’t make you a criminal. You’re only a criminal if you (a) infringe for profit, (b) infringe more than $1,000 worth over a 6-month period, or (c) put a pre-release copy online.
The same is basically true of the DMCA (chillingeffects.org):
Question: What are the penalties for violating the DMCA's anti-circumvention provisions?
Answer: The DMCA allows for both civil remedies and criminal penalties for violations under the anti-circumvention provisions. If the violations are determined to be willful and for commercial purposes or private financial gain, the court can order significant fines and/or imprisonment.
This work (the xkcd comic) is licensed under a Creative Commons Attribution-NonCommercial 2.5 License.

