6. Lauryn Hill

Lauryn Hill and her band, The Fugees, were among the biggest rap stars of the 1990s, hitting the top of the charts around the world with tracks like 'Ready or Not' and 'Killing Me Softly.' Hill followed that up with a massively successful solo album 'The Miseducation of Lauryn' Hill, which spawned further smash hits like 'Ex-Factor' and 'Doo-Wop (That Thing'). If you're wondering how he could now be out of money after so many record sales, remember the key point; it was the 1990s. How many times have you seen her trouble the charts in the twenty years since?

As with so many big stars, a reluctance to pay taxes was the cause of Hill's downfall. The interesting excuses she offered for not paying, which included 'it disturbs my creativity,' and 'I'm being manipulated,' surprisingly didn't wash with the IRS. If anything, it just appeared to anger them. As well as being ordered to pay more than half a million dollars in back taxes, Hill spent three months in jail.

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