As is characteristic of most living legends, hip-hop's first billionaire leads a life marked by constant evolution and cloaked in a bit of mystique.

From his start in the "underground economy," as author and friend Dr. Michael Eric Dyson writes in his biography, Jay Z: Made in America, to becoming the contemporary businessman fans and critics know today, Hov has kept his finger on the pulse of the culture. Lyrics from hip-hop’s first billionaire — as candid as they are catchy — have narrated some of the trials and triumphs of the Black man in America, starting with his 1996 debut, Reasonable Doubt, up to his most recent feat, 4:44. Indeed, the hustler-turned-rapper has been endowed with nine entrepreneurial lives. And his lyrics capture every evolution. Here are five times Hov’s wisdom pushed the culture forward.