Jay-Z Gets Deep On 'Diary:' Watch A Classic Clip Now!

In celebration of Jay's Magna Carta Holy Grail, MTV News looks back at some classic Hov moments.

In 2000, Jay-Z was already four albums into his career and was gearing up to release a fifth. He'd broken through with hits like "Hard Knock Life" and "Big Pimpin'," was expanding his Roc-a-Fella roster and had branched out into the business world with the launch of his Rocawear clothing line.

In essence, he had begun his transformation from mere musician to mogul, and with his status on the rise, Jay decided it was time to help bring others to prominence. The album he'd release in September, The Dynasty: Roc La Familia saw him eschew big-name producers in favor of up-and-comers like the Neptunes, Just Blaze and Kanye West, thereby helping launch their careers too.

And while his fame helped those around him, Jay was still coming to terms with his celebrity, trying to strike a balance between his public personae and his private life. As he told MTV's cameras that year: "Shawn Carter is before the music business. Their perception of Jay-Z is a little different than their perception of Shawn Carter, but to me, they're the same person."

And though Jay was reaching new heights, he was also determined to remain loyal to his roots. Which is why, exactly one month before the release The Dynasty, Hov took MTV's "Diary" around his beloved borough of Brooklyn, to places like Junior's on the corner of Flatbush and DeKalb (ironically, just blocks away from where Jay'z Brooklyn Nets would tip off in 2013), and, of course, his former stomping grounds, the Marcy Projects, where he reminisced on a childhood that was anything but innocent.

"I grew up in Marcy Projects, with a sense of worthlessness ... I didn't have no direction," he said. "People would get shot or killed, and it would never be in the paper, or on the news, so we was like 'Our life ain't even worth reporting.' No one cares if we live or die, and that's where that mentality comes from: 'I'ma get it or I'ma die trying.'"

It's a frank and fascinating look at a man at an early crossroads in his career; and, now, as Jay prepares to release his next opus, Magna Carta Holy Grail we're bringing back a segment of his classic "Diary" episode. After all, it's impossible to measure how far you've come if you don't look back ... and we're pretty sure Jay would agree with us on that.