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372. R. Kelly

Before he became primarily known for his personal shortcomings in the pursuit of underage women, R. Kelly made a claim to the R&B throne.  His music was Soulful and smooth and his ability to be lyrically blunt about sex yet do so without coming off like a parody.  Combine these skills with an ear for current Hip Hop beats and you had a talent who truly had his finger on the musical pulse of America.  The skills of R. Kelly are unquestionable, but so was his penchant for underage girls.  Chances are his career as solid as it was can’t overcome that giant blemish on his personal life. 

36. PJ Harvey

One of the most critically respected female artists of the last thirty years, P.J. Harvey could be classified in so many ways.  Singer/Songwriter.  Lo-Fi Superstar.  Alternative Goddess.  Frankly, we could come up with so many more.  

225. Mary J. Blige

Since her debut album in 1992, Mary J. has shown an evolution from a streetwise Hip Hop star to a Soulful Diva.  Her tough sexuality has made her an icon and her career progression shows no signs of slowing down.  The amazing this is with Mary J. Blige’s progression she kept her initial fans while obtaining new ones.  This type of cross over appeal and career consistency makes her stronger every year.  There is a greater chance here than you might think.

126. No Doubt

The Ska/Pop hybrid that No Doubt created in the mid 90’s found a huge following and made Gwen Stefani the Debbie Harry of her era.  No Doubt managed to gain both an Alternative and Pop following, though their future efforts were primarily danceable Pop.  Stefani is the key here, as her solo career skyrocketed and though it was not necessarily in the Rock vein, her overall efforts (which is still growing) could propel her band to Cleveland.