#67 Jay-Z, 'Reasonable Doubt' (1996)

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