First answer (varies from country to country) is "yes." In your country if you do not own a physical version (LP, cassette or legally downloaded version) of the item in question then it is illegal and you'll open yourself up to fines and possible jail time (though the latter is unlikely). It would be tried by the feds who would use the "prove you didn't sell it" tactic.
Out of print works the same as books. The fact that it isn't in print doesn't mean it isn't under copyright. Just ask Amazon. Copyright does expire but they are also moving to change that number of years IMO for monitary gain.
Pick up the latest Wired magazine and/or read one of the best current authors on the subject, Quinn Norton. She writes for both Wired and MaximumPC magazines. Her main focus is legal journalism for the digital age.