OK, despite the fact that this story doesn't really involve an actor who benefits in many, many ways from copyright law... This fictitious performer can start by setting a good example - post his productions for free on the web, under the terms of Wikimedia Commons.
The "I bought it, I own it" crowd do miss the point of copyright. If they buy a print book or a vinyl audio disk, or a CD, they do own the physical stuff - the paper, the ink, the plastic. They do not, and never did, have the right to distribute copies of the words printed on that paper, the sound encoded on that disk, the words, the music....
When my kids inherit my library of print books, CDs, and DVDs, they have a few choices - sell them at the estate sale, toss 'em in the dumpster, donate them, maintain the library as a shared resource, or divvy it up. "You take the classical, I'll take the jazz. You take Simon, I'll take Garfunkel." The one thing they cannot do legally is duplicate those books (well, those that are still under copyright protection). "We both inherited it, so we're both entitled to our own copy" just doesn't work, unless they want to spend the money to buy new copies of each item in the library.
So, the hypothetical Hollywood stars' kids are already way better off by having access to Dad's iTunes Store account. They can both use the same AppleID to access Dad's Library. Heck, they can keep adding to the library, and share the new stuff as well. As long as the tunes remain on Apple's servers, they can download them again when they lose their iPods, or their computers melt in a fire. Seems a whole lot better than what might happen to Dad's books, CDs, and LPs if a fire sweeps through Topanga Canyon, or the house surfs a mudslide down into the valley.
So, what's the issue? Why do we cease to understand copyrights when we're talking about digital files? Because digital is so easy and cheap to copy? Because it's not likely we'd be caught? That's not what I'd call "moral high ground."
The songs on our black vinyl records do not belong to us. They never did. We can't claim we're the songwriter because we plunked down $12.95 for the disk. We own a piece of plastic that lets us experience the copyrighted performances impressed into that disk, for as long as it lasts.
The songs encoded in that MP3/MP4/AAC... do not belong to us either. We purchased the right to experience the performance, the same way we do when we go to a movie theater or concert. We purchased the use of one seat in the theater, not the right to open the fire exit and let all our friends in.
Today, since it's so easy to make copies, End User License Agreements (EULA) are attached to everything. Why? Because too many people think things are different today than in the past. "The Internet and computers have changed everything." Wrong! It's no different. A song is still a song, a story is still a story.
The EULA is little different than most publishing and entertainment contracts, going as far back as such contracts have existed ("I tell you story, you give me meat... and story really good, so you give me big piece of meat. You invite other tribe? They give me big piece of meat, too"). Since digital technology makes it so easy for us to copy and distribute the works, we have to be treated more like a publisher or movie studio, rather than an innocent consumer. "Here's what you can do. If it's not on the list, you don't have the right to do it."
It doesn't matter that we think the original performers got ripped off by the record label. We're not a judge, we're not a jury. We're just kids stealing fruit from the mean grocer down the street because we don't like him.