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.

1. "I believe you can speak things into existence."

The highly decorated rapper holds the spot for the most No. 1 albums on the charts, according to Billboard. So yeah, Jay may know a thing or two about manifesting his dreams. 

2. "A wise man told me don’t argue with fools, because from a distance you can’t tell who is who."

In an interview with The New York Times, Jay revealed he was surrounded by threats to his success growing up in the Marcy Homes housing project in Brooklyn. The rapper and proud product of therapy opened up about who he had to become to survive his environment and the reality that you can’t take everybody with you.

3. "Identity is a prison you can never escape, but the way to redeem your past is not to run from it, but to try to understand it, and use it as a foundation to grow."

Indeed, like any true creative, the rapper embraces his demons along with his angels — and channels them into his art. His latest studio album, 4:44, earned him eight Grammy nominations and invited fans into his innermost reflections and regrets. 

4. "You egged Solange on knowing all along, all you had to do was say you was wrong."

After three years of deafening silence, critics and fans hear the rapper’s response to the fateful elevator incident, involving Jay-Z and sister-in-law, Solange Knowles, on 4:44. On the album’s opening track "Kill Jay Z," the rapper laments his own lack of accountability for his fight with Solange, later revealing in interviews that his infidelity lay at the center of the family tension. 

5. "I believe everyone in the world is born with genius-level talent. Apply yourself to whatever you’re genius at, and you can do anything in the world."

Taking full advantage of 4:44’s captive audience, the businessman and advocate served up some hearty financial advice in between bars. Rapping on the album’s second track, The Story of O.J.: “I bought every V12 engine/Wish I could take it back to the beginnin'/I coulda bought a place in Dumbo before it was Dumbo/For like two million/That same building today is worth 25 million/Guess how I'm feelin'? Dumbo…” the rapper reflects on a missed opportunity to invest in Dumbo, a Brooklyn neighborhood on the rise. Later on in the track, he asserts: “Financial freedom my only hope/F**k livin' rich and dyin' broke/I bought some artwork for one million/Few years later, that shit worth eight million/I can't wait to give this shit to my children.” 

Alas, to quote the billionaire's own evolving wisdom: the only true freedom is financial. And keeping your head on a swivel may be the surest way to achieve it.