The radio usually pays a license fee to the local performing rights authority and the authority then pays a percentage of license fees to the artists. That’s a very watered down version, but essentially how it works.
The authority then handles the back end admin of managing who gets paid, different artists and their labels have different requirements and royalties and all of that is often negotiated through deals, so there are many many variables to how it works. But as far as the radio station is concerned, they pay a license fee to be allowed to play the music, then the authority takes care of the rest.
I believe the radio station also sends a report to the authority on a regular basis to show what was played when to determine actual royalties for each artist.
Tldr: the radio station pays a fee to a regulating authority to play all music the authority represents, then sends its playlist to the authority regularly. The authority then pays artists. The artists and labels sign with the authority to manage royalties.
There are organizations that track it (BMI, ASCAP in the USA). Artists registers their songs and then BMI/ASCAP collect the royalties and distribute them. The collect playlists from stations, list to stations and track what is being played, visit bars / theatres to see what is being played. Calculate stats on what songs are played the most and then distribute royalties. It is not exact, they can’t track every radio station, station, theatre, bar, etc that has music playing.
There are also rigs that scan 40-50 channels at a time (radio, TV, cable, etc). It can then compare the commercials played with the commercials billed. This is the sort thing that really just requires a large closet, power and Internet and I know some people who would rent these out and you get a small amount per month to have it double check on what the stations say and what they do.
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