After two singles, Jay-Z bucked the trend, and kicked his much sought-after deal to the curb. With this he had started making a name for himself and was signed to Payday Records. He started selling tapes out of the boot of his car. He was brought to the attention of Big Daddy Kane, who had taken him on tour but he still struggled to get a record deal. In this case, he had started dealing drugs to make ends meet. Desperate to be a rapper, Jay-Z did anything he could to support himself while pursuing the dream. He performed on a few of his singles before Jaz-O was dropped from his label. In 1989, 20-year-old Shawn Carter aka Jay-Z was mentored by rapper, Jaz-O (that’s where his moniker came from).
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