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James Kaplan: Straight Outta Hoboken

[James Kaplan is the author of “Frank: The Voice.”]

TO the best of my knowledge, Frank Sinatra acknowledged the existence of rap music only once in his life: at the lavish 1995 tribute in honor of his 80th birthday, after the hip-hop trio Salt-n-Pepa performed a special-lyrics version of their hit “Whatta Man,” he turned to his wife, Barbara, and said, “Marvelous.”

That was, in all probability, the obligatory Hollywood “marvelous.” Yet Sinatra, who would have turned 95 today, surely would have been flattered and amused — bemused, too — at the lavish attention and respect tendered to him over the past two decades by rap musicians. A case in point: the 2005 album “Blue Eyes Meets Bed-Stuy,” whose tracks mash up such Sinatra songs as “For Every Man There’s a Woman” and “Fools Rush In” with raps by the late Biggie Smalls (a k a the Notorious B.I.G.) like “Nasty Boy” and “10 Crack Commandments.”...

Frank Sinatra adopted a tough outsider’s stance, as a defensive posture, from the beginning of his career. The image lingers. His defiantly staring 1938 mug shot (taken after the first of Sinatra’s two arrests that fall, for the no-longer-on-the-books charges of seduction and adultery) has been reproduced innumerable times, on T-shirts, coffee mugs and posters that show up in college dorms, not to mention on the wall of the Bada Bing strip club in “The Sopranos.”...
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