Eagles

The Eagles mastered the art of catalog monetization decades before streaming made it trendy. Their 1976 album 'Hotel California' alone has generated over $100 million in revenue, while 'Their Greatest Hits 1971-1975' became the best-selling album in U.S. history with 38 million copies sold. But here's the genius move: unlike many 70s bands who sold their catalogs cheap, the Eagles retained their publishing rights and now earn massive royalties every time 'Hotel California' plays in a movie, commercial, or gets streamed.

Their touring strategy reads like a masterclass in premium pricing. The Eagles pioneered the $100+ concert ticket in the 1990s, famously telling critics 'if you think our tickets are expensive, don't buy them.' Their 2013-2015 'History of the Eagles' tour grossed over $250 million, proving that legacy acts could command top dollar. Even after Glenn Frey's death in 2016, the band continues touring with his son Deacon, maintaining their premium pricing model while introducing the catalog to new generations.

Don Henley's business acumen extends beyond the band, as he's become one of music's most vocal advocates for artist rights and fair streaming compensation. His individual net worth of $250 million reflects not just his Eagles earnings, but smart real estate investments and his successful solo career. Joe Walsh ($75 million) and Timothy B. Schmit ($25 million) round out the current lineup, while the late Glenn Frey's estate maintains significant value from his writing credits and solo work, proving that great songs truly are annuities that keep paying.