Shoulda, Coulda, Woulda: 10 Celebs We Thought Would Blow Up

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Amy Winehouse

The British singer who was trained at the prestigious BRIT School (former pupils include Adele and Leona Lewis) had a voice that could wake a man from a coma! Not only could the Jewish-raised songstress sing, but her lyrics were honest and raw. Unfortunately, a series a bad relationships and drug use took her from the limelight and into rehab (a few times).

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