Legal Question in Intellectual Property in California

Not sure what you mean. A "play-list" is a document listing songs that played on a particular day/week/month, etc.

If what you mean is that your friend has a disk full of recordings, then IF those recordings were legally acquired by the radio station (without any restrictions), then they can be sold ONE TIME... under the "first sale doctrine"

Trouble is, most record companies provide music to radio stations on a NFR (not for resale) basis... so the material can't be sold.

So, I'm afraid the answer is "it depends" on facts you haven't provided.

Your friend should consult an attorney, and provide all the details. Only then can the lawyer give meaningful advice.