‘New York Times’: Jay-Z Had Tougher Upbringing Than Sinatra

In “Empire State of Mind,” Jay-Z declared that he’s “the new Sinatra.” And in a New York Times op-ed, writer James Kaplan argues that Jay’s assertion that Sinatra had “a little tougher [upbringing] than mine” is wrong. Kaplan, author of the recent Sinatra biography The Voice, writes: “In fact, Jay-Z, who grew up with a single mother in the drug-and-bullet-riddled Marcy housing projects in Brooklyn, had a much tougher youth than Frank Sinatra, who was the only child of upward-striving, financially comfortable parents in Depression-era Hoboken, N.J.”

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The article — which was published to commemorate what would have been Sinatra’s 95th birthday — further examines connections between the late singer and hip-hop. “Sinatra’s unfortunate flirtations with the Mafia later on — much like the gangsta affectations of many rappers — had more to do with being a wannabe, an idolator, than any actual mob affiliation,” Kaplan writes. (In his new memoir, Decoded , Jay discusses his days as a drug dealer at length.)

Yet that affectation, Kaplan argues, was far from Sinatra’s greatest strength — in fact, the opposite was. Sinatra’s “vulnerability is at the core of his magic,” he writes. “There was an operatic intensity to Frank Sinatra’s existence. … The conflicts filter into the molecules of his music. We hear, we respond.” Indeed, he writes that Eminem’s “Not Afraid” is a stellar example of how the best rappers attain a similar goal, exposing “the sorrow and humanity that underlie the swagger.”

Straight Outta Hoboken [New York Times]