Putting Chappelle and Swift aside, I do think it's different when you're a creator vs. just a performer. Taylor wrote her music. Chappelle (I assume) wrote and contributed a great deal to his show along with the rest of his writing staff. It's like a composer or playwright holding onto their rights vs. an actor expecting to get residuals into infinity. I also think it's different when you are a musician or a stand up or some other performer where you can still perform your old songs or tell your old jokes. For most actors, directors, etc. once that project is finished, you're done with it. There might be a sequel but unless they remake it, you shouldn't really expect to earn money off the same material. That's why smart actors are always looking for their next gig.