8. Madonna
Oct. 10
$43 million
Some 25 years after she emerged as pop music's most bankable provocateur, the 49-year-old mother of three shocked her fans again by dumping her longtime record label Warner Music in favor of a 10-year, $120 million deal with concert promoter Live Nation. Madonna pocketed an $18 million signing bonus, plus another $25 million in stock. She'll score $17 million advances for each of her next three albums under Live Nation. (She owes Warner one more studio album and a greatest hits collection before she bails.)
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