Chief Keef
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At 19, Chief Keef is the youngest rapper on our list. Despite his years he’s been in and out of jail and his lifestyle epitomizes that of the youth gang violence in Chicago. His track “I Don’t Like” was remixed by Kanye West and led him to a multimillion dollar deal with Interscope records. It’s now been some time since anyone’s heard anything from him, so it’s only a matter of time before those funds run dry.
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