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How Jay-Z’s Affection for This Classic Musical Helped Create One of His Biggest Hits

February 27, 2026
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How Jay-Z’s Affection for This Classic Musical Helped Create One of His Biggest Hits

It’s been a long time since Jay-Z could’ve been considered an underdog. He’s been a billionaire for years, a millionaire for even longer. He’s widely considered one of the greatest rappers of all time, if not the definitive choice. When you’re married to Beyoncé, how much of an underdog could you really be?

Still, long before he was running the NFL halftime shows and trying to build casinos in Times Square, Hov was just a man from Marcy Projects. A one-time drug dealer from Brooklyn, there was a time when he was scratching and clawing to make his way into the music industry. Jay-Z cut his teeth with longtime mentor Jaz-O before becoming the head of Roc-a-Fella. By 1998, he cemented himself in hip-hop’s hierarchy, leading the charge amidst the tragic deaths of Biggie and Tupac.

Plenty of artists have told us how they made something out of nothing. But Hov went one step further, comparing his arc to the musical Annie. It’s a daring move to depict the rags-to-riches story around such a whimsical sample. But for the rap icon, it was all about formulating the narrative of the hard-nosed underdog.

Jay-Z Explains Why It Made Sense to Sample ‘Annie’ for ‘Hard Knock Life’

In a 1999 interview, Hov spoke with London journalist Dan Gennoe for Flipside Magazine. There, he painted the picture simply. An orphan getting the opportunity to live with a rich family is translated to a former drug dealer trying to overcome the odds. The details don’t make it a seamless comparison, necessarily, but the core idea was simple. Jay-Z made it to the top just like Annie did, and he did, in fact, end up liking it there.

“Everybody likes a story like that, when the underdog wins. The orphan gets to live with a rich family. I wanna live with a rich family too. Anybody from a poverty area does, you know? That’s a story you can relate to. I tell people all the time, I been famous four years, I been alive way more than that,” Jay-Z said. “(The struggle) doesn’t just go away like that, it’s still in me.”

With the underdog story fully accomplished, what did Hov want next? Ultimately, his resolve isn’t that unfamiliar. He really wanted to thrive as a businessman and build generational wealth, so that his hard work would benefit his future kids. As much as he loved to rap, Jay-Z wanted to take more of a backseat and dictate the field from behind the scenes. However, there was never a doubt in his mind that he could build his empire again if he needed to do so. “I think I have the drive, determination, and belief in myself that I could definitely do it again,” Hov emphasized.

The post How Jay-Z’s Affection for This Classic Musical Helped Create One of His Biggest Hits appeared first on VICE.

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