Jay-Z is the second wealthiest man in hip hop, and since 1995, Hov has been bringing us quality music. From Reasonable Doubt to 4:44, the Brooklyn rapper has been around since the days of Big Daddy Kane and Biggie. As one of the first artists from the genre to achieve billionaire status, Hov (real name Shawn Carter) is considered to be one of the best rappers of all time.
Before Jay-Z exploded onto the scene in the late 1990s, he was an aspiring rapper who was just around. He was ubiquitous and persistent in his aim to prove that he was a certified rapper and did so by constantly adapting and affiliating himself with those more prominent than him.
In his quest to attain exposure, during the 1980’s Jay-Z affiliated himself with Jaz-O. Jaz-O (real name Jonathan Burks) was a Brooklyn rapper, born and raised in the same housing scheme as Jay-Z, the Marcy Houses. Burks knew Jay-Z from his area, and in a bid to help a young Jay-Z, Jaz-O allowed him to become part of his entourage.
While aligned with Jaz-O, Jay-Z even appeared in the video for ‘Hawaiian Sophie’ and during his stint as part of the rapper’s crew, Jay-Z got to network and meet people. One of those people was Big daddy Kane, another bigshot Brooklyn rapper.
After meeting Jay-Z and seeing his skill, Big Daddy Kane took him under his wing, and Carter became Kane’s protégé. Going everywhere with Kane as his young prodigy child, Jay-Z even appeared on television. In the 1980s and early 90s, there was a tv show called Rap City. In 1990 Big Daddy Kane encouraged Jay to drop a TV freestyle. The result was Jay-Z’s first ever televised freestyle. In the video, the rapper is 21 years old.
Jay-Z was also Big L’s affiliate for a while. He also hung out around Biggie Smalls for a period during the 1990s. You can watch the Rap City freestyle below.