Downvote Downvoted: OP was just stating his opinion, not claiming that Mr. Willis had necessarily waived any rights. Besides, a licensee has no rights* to licensed material other than those conveyed by the license he agreed to.
Furthermore, the existence of illegal or unenforceable terms does not negate the necessity of reading and understanding the terms of any contract one enters into. Most modern contracts include a clause, which has been held to be legal, which states that if there are any illegal terms in the contract, those terms are null and the rest of the contract stands.
Many software licenses include a non-transferable clause which has held up in court (for a good example, research the legal history of AutoDesk's AutoCAD license.) That would easily cover this "legacy" scenario. So unless Apple's lawyers really messed up, or a judge were to find a substantial and relevant difference between music licensing and software licensing, Mr. Willis is not likely to succeed.
PS. It's waive. You can wave your rights all the way to the bank, but you'll just look like a fool.
* Technically, "fair use" and other similar constructs are not licensee rights, but exceptions to rightsholders' rights of enforcement.