5 Pink Floyd
Members of both the U.K. and U.S. Rock and Roll Hall of Fame, Pink Floyd rode the wave of British success that started in the mid '60s and never slowed down. They toured through 1994, sold merchandise that has probably appeared on more dorm-room walls than any other band in history and sold more than 200 million records across the world. Although they were repeatedly plagued by poor financial decisions, the sale of the estimated 44 million copies of "Dark Side of the Moon" alone probably made up for any bad investments.
4 Led Zeppelin
The band that oversaw the transition of rock and roll into heavy metal is not just one of the most influential bands in history, but also among the most profitable. The second-best selling band in the United States behind only the Beatles, Zeppelin has had at least four record-breaking tours and is estimated to have sold 300 million records worldwide. How much of their fortune has been squandered to the over-indulgent, hotel-smashing debauchery for which they are almost as famous as for their music, no one will ever know.
3 The Beatles
Widely considered to be the most influential, if not the greatest, band in the history of rock and roll, Western music can be broadly divided into two categories: Before the Beatles and after. Their music was the soundtrack that played behind a decade of some of the most profound change in American history, and the Fab Four cashed in big time. Just a year after they led the 1964 "British Invasion," they had already sold an astounding 100 million records worldwide. By 1972, they had sold 545 million records. To date they are the best-selling band in both the United States and Great Britain.
2 The Grateful Dead
It's ironic that the godfathers of the hippie movement, which rejected commercialism, were as close to a corporation as a band can ever get. The group toured essentially uninterrupted for 30 years from their formation in 1965 until the death of frontman and spiritual leader Jerry Garcia in 1995. But selling out stadiums for three decades was nickels and dimes compared to the band's unrivaled merchandising campaign. Represented by legendary entertainment lawyer Hal Kant, the band pioneered intellectual property management in music, which led to piles of cash collected from their loyal "deadhead" fans, who continue to buy mountains of merch, including everything from Dead Red wine to posters to stickers to T-shirts to Cherry Garcia ice cream.
1 Elvis Presley
Long before Shakira sung her first note, Elvis Presley's hips didn't lie. Although not a band, Elvis still epitomizes rock and roll nearly a half century after the passing of the generation he defined. He is the best-selling solo artist in the history of recorded music, and saw astounding success across several genres as well as on the big screen. With more than a billion records sold, he remains one of the most recognizable—and successful—cultural icons in American history. Forbes estimates that the King's estate made $35 million—last year alone.