Send the 1099 to the individual or entity you paid the money to. It is that simple.
I cannot be responsible for your case until such time as I am in an attorney-client relationship with you. To do so, I require a written Fee Agreement so you know the fees I would charge to handle your case. I can represent you before the IRS if you retain me as I am a licensed attorney and can represent taxpayers from any state.
I'm not sure I understand the question. But if you or your company paid the IC more than the $600 then you would report that on the 1099-MISC. It does not matter what anybody else did or did not do.
You may want to consult a tax pro near you to clarify.
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If you are running a record company or management company, you must make sure to lay the proper legal foundation. The company should have systems in place for automatically sending out 1099 forms to independent contractors (in this case, artists) who receive compensation from the company. Your company needs a team which includes intellectual property/business counsel and an accountant. Your accountant should be consulted regarding this particular issue. My guess is that you should immediately send out the 1099, but your accountant needs to advise you based on his understanding your how your business is set up.
I am worried about hour characterization of your deal with the artist as a "360 Deal w/management". There are many different various of "360 Deals" and it is critical to have a properly drafted and negotiated written contract with your artist. This needs to be handled by experienced music/intellectual property licensing counsel. You should not be attempting to prepare contracts like this without legal assistance. Also, be careful about holding yourself out as an artist manager or agent. In most states, you need to be licensed to serve as an agent to an artist, or a booking agent. Many people make the mistake of believing they can call themselves "managers' without complying with the licensing requirements. This is particularly important in a "360 deal" because the record label often can be viewed as facing a conflict of interest with the artist. Frankly, the record label should not be managing or representing the artist in a proper "360" deal---the artist should have separate management. Otherwise, this conflict of interest could lead to big trouble for you later on.