This is a design by MS Paint Adventures. I don’t know if there’s a back story here, though there usually is with these shirts designed by comic artists, but the design stands on its own, because the lo-fi, pixellated design is cool looking and it’s a nice representation of a common theme, broken record. This particular record is riven by a lightning bolt, which gives it some kinetic energy.
You want this Dave’s Broken Record T Shirt. I’m pretty sure of it. It’s available over at Topatoco.