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Lauryn Hill: The Loner, $9 million

This highly talented (yet heavily controversial) singer and rapper changed the face of hip-hop and R&B during her most active years. With her early work in the hip-hop group The Fugees, Lauryn Hill commanded respect as a female emcee and then went on to smash records with her 1998 solo debut “The Miseducation of Lauryn Hill.” It sold 18 million copies over the next decade and earned Hill 10 Grammy nominations and 5 wins in 1999. After this smashing success however, Hill became entangled in a multitude of difficulties, and began to recede from the spotlight. Over the years there have been quiet murmurings of a comeback album or Fugees reunion, yet nothing has ever materialized. Some speculate this has been the result of Lauryn’s reputation for increasingly odd behavior and business methods. Despite her mysterious actions, Lauryn Hill still sporadically tours. She maintains a reported net worth of $8.7 million dollars gleaned from performing, record sale royalties, and various investments in Jamaica and abroad. Thankfully, managing her finances was one thing Ms. Hill was not miseducated on.