> Streaming brings in a fraction of cent per play so his catalog can't be generating more than a million dollars per year at best.

Wow, I think that's wildly off the mark. Bob Dylan probably has several billion streams per year, if not more. On Spotify right now, his top 10 songs have a billion streams. Obviously those did not all occur in a single year, but Dylan's catalogue is deep, and Spotify is hardly the only platform.

One billion streams per year is about $4 million on Spotify.