If you’re familiar with Jay-Z’s story, you know that he didn’t have the best relationship with his father. During a conversation about the song “Where Have You Been,” he revealed that he finally saw his father for the first time since childhood while making The Black Album, but not before going through some of those same issues that led to their falling out initially.

His mother convinced him to have a conversation, and he agreed; however, his father flaked on him, which caused those bitter feelings to resurface. Yet, Jay still found the courage to set aside his ego for his mother after she pleaded with him to give his father one more chance. They eventually met and had one of those mature, life-altering conversations that you didn’t think could still happen after reaching adulthood.

The thing is, after finally rekindling his relationship with his dad and helping him get on his feet by putting him in an apartment, his father — who Jay described as a cool dude and good at basketball — sadly passed away a month later from liver failure due to years of drinking and drug use. It was a rare moment of vulnerability for Jay and one of the deeper conversations in the series so far.

One of the more interesting aspects about artists of Jigga Man’s stature is their studio habits. There are great stories about other rappers, like Eminem who treats his studio time like a 9-5 job, adhering to a strict schedule and even taking lunch breaks. On the other hand, there’s someone like Ye (formerly Kanye West), who works around the clock and takes his entire production crew to Hawaii when creating My Beautiful Dark Twisted Fantasy. Jay’s routine, like his personality, is more laid-back. He mentioned that he usually arrives around 2-3 p.m. and stays until 10:00 p.m., even stating, “You could set your clock to it.” He also said that he rarely records overnight and often collaborates with producers to edit music under his vocals during post-production, telling Rick Rubin that “Song Cry” sounded completely different at first.

Jay has a famous line in the first verse of his classic song “Where I’m From” from his sophomore album In My Lifetime, Vol. 1, where he raps, “I’m from where n—as pull your card and argue all day about/ Who’s the best MCs: Biggie, Jay-Z or Nas?” He admits that he purposely inserted himself into a conversation that didn’t necessarily align with what actually happened during that specific period.

“I actually was inserting myself into an argument that I wasn’t even in yet,” he confessed. “You know, they were talkin’ about me heavy on a street level, but I hadn’t had mainstream success — and these guys were already pretty much mainstream artists.” It served more as a hot line at the time but ended up being prophetic since he’s now widely regarded as one of the top five MCs or even the GOAT by many.

While still discussing the era between his debut album and rise to commercial stardom with Vol. 2… Hard Knock Life, he talked about wearing a bulletproof vest during a photoshoot while crafting his second album and filming Streets Is Watching. He explained that he still had ties to the drug game and was actually in conflict with a rival crew; thus, wearing the vest was more functional than stylish as he transitioned from street life to fame.

Jay said he arrived at the shoot wearing the vest, and the photographer liked it so much that he encouraged him to keep it on. The visual of him sporting the bulletproof vest over a white t-shirt along with a Rolex has become one of his more iconic looks. He revealed that one of the first times he met late Nipsey Hussle, the West Coast MC brought up this look — and Jay wore it during three shows at Yankee Stadium last summer.