Once this crap becomes ubiquitous, why would companies ship unencrypted bits at all? They could send files encrypted with all the major OEM "protected content" keys. If you're running on non-supported hardware, well, sucks to be you, pirate. I imagine it's rather difficult to extract the private key from DRM hardware.
In the end, big media wins.
1) For DVDs there were only a handful of player keys, like less than 30 if I recall correctly. Once they were all leaked the system was broken forever. AACS as used on BluRay has so many keys and such efficient revocation that each player can have its own key.
2) The BluRay designers realised that AACS by itself was insufficient because it takes time to revoke a key, and if they leak faster than they can be revoked the total quantity doesn't matter much. So they did BD+ as well, which is basically a kind of band-aid to detect emulators using stolen keys.
BluRay security has definitely been more effective than DVD security, especially in its earlier days, but the leak of the HDCP master key was pretty fatal, and eventually (all proprietary) emulators got good enough that BD+ programs couldn't really tell them apart from legit licensed players.
They already did that, twice.
What's more, in the past media distribution was on physical disks and players weren't on the internet, so software couldn't be upgraded. The future is obviously in downloads and streaming, which will enable a bunch of new things.
Key rotation will be much simpler as vendors can just issue a compulsory automatic upgrade. As a different download can be prepared for every customer, there's no need for keys to be shared by multiple customers. Every download can be watermarked so anything that does get out can be traced to a particular downloader.
So I don't think the failures of the past indicate it's impossible for DRM to ever work.