[kmeisthax]

"Sufficiently clever AI" would, in this case, be the person writing a reverse-engineered work alike app.

In some of the cases mentioned (e.g. Spotify, Chegg, etc) you can't really do this, because the actual value in the app is just the copyrighted material being purchased. Reverse-engineering is protected under US law for a variety of reasons, mostly that you can't copyright basic functionality (that's for patent law) and that copyright shouldn't extend to interfaces[0].

AI trying to reverse-engineer all of music or art or writing already exists. They're called MuseNet, DALL-E, and GPT-3 respectively. While you can sort of trick them into regurgitating training data in a way that would make their use to create novel works legally perilous, it's still kind of difficult to get them to generate exact copies in a way that would be useful for "pirating" all of Spotify.

[0] SCOTUS tried very very hard in the Google v. Oracle decision not to actually say this. However, the actual ruling has a similar effect.