This is extrapolated the chapter I’m reading (“The Short Head”) in The Long Tail by Chris Anderson, so the idea isn’t really even 100% mine. But feel free to go for it.
You know how Amazon pairs items together? “Buy The White Album together with Abbey Road for $21.95″ or something similar? Amazon isn’t giving me any news by mentioning that Abbey Road is also a Beatles album, and there’s a good chance that I’ll like it if I want the other.
When someone goes to purchase something well-known, feed them an opportunity (with an awesome deal) to get something from the long-tail paired with it. iTunes shows the “Listeners Also Bought” section, but this is mostly meaningless in the long tail. For instance, iTunes shows that listeners who bought Uncle Widget’s Bedtime on Mars (children’s music) also purchased Gnarles Barkley (one-off pop) and John Mayer (adult contemporary pop). The closer you get to the head, the more meaningful (until you’re well into the head, then it often resorts back to pairing John Mayer and Gnarles Barkley).
It would make sense to ask (in a slightly limiting fashion) media buyers or music submitters to assist with these pairings so that it doesn’t become a resource drain. Go ahead and let me know when you’re done. I’m on board.