Like, if you are selling access to content, the producers are reasonably entitled to a share of your revenue. But if the producers sign their rights away (granting "entity" an exclusive license to sell reproductions) they are entitled to whatever you signed to pay at the dotted line, only. That's how the content industry was run since forever.

When those licenses are written as non-exclusive, you might have a gnarly mess of Guitarist and Singer authorize Band authorizes Agent authorizes Advertising Partner authorizes Radio Station authorizes Distribution Company authorizes Pandora/Netflix authorizes Partner, and Friends. If one of those contracts goes south (non-payment or expiration), are all of the subcontracting child parties suddenly violating criminal law and liable for jail time because they're now distributing copyrighted works without authorization?

Of course not, they are in breach of contract, or in a contract dispute, or a failure to achieve a meeting of the minds, or whatever. You don't go to jail. Not in any reasonable society, at least I would argue. Not before one of the entitled parties says "cease and desist," and after you fail to comply within a reasonable period of time, and even then certainly not before a judge says so.