Last year, we did a series of five Artworld Roundtables in collaboration with Chris Richards, the pop music critic for the Washington Post. Richards posed the “five hardest questions in pop music”: “cultural appropriation, problematic lyricism, selling out, the ethics of posthumous listening, and … separating the art from the artist.” In response, we rounded up several thinkers working in these areas to see what they had to say about each question. Richards provided us with key examples to draw out the problems and complexities of each debate. The results are here: cultural appropriation, how to respect the wishes of dead artists, whether selling out is still possible, how to engage with objectionable lyrics, and separating the art from the artist who created it. And now Richards is back. Read on to see what he took away from it all.