At San Quentin
Johnny Cash

Another easy 5. Even covers/performances of him are top tier. In the recent Dylan biopic Cash and the Tennessee 3 have a shirt musical cameo (not even a full song) and it blows all the other music performances out the water. I enjoy when he plays a song about how shit life in that prison is, gets thunderous applause, has a laugh at the guards expense, then plays the same song again.

5