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.”
Biggie’s friend and colleague Jay-Z has made references to Sinatra in several numbers, and even recorded his own version of “My Way.” In his 2009 song of himself and New York City, “Empire State of Mind,” Jay-Z proclaimed himself “the new Sinatra.” And while he may be no Sinatra vocally, his complex and catchy paean to the Big Apple (with Alicia Keys singing backup) has made strides toward supplanting Frank’s bombastic “New York, New York” as a city anthem: witness the Belmont Stakes’s replacement of the older song with the newer in its opening ceremony in June.
Not to be outdone, the ubiquitous entrepreneur and sometime rapper Sean Combs has dubbed himself “the black Sinatra”; still another rapper has taken the phrase as his very own nom de hip-hop. “The alias Black Sinatra came into play due to his cool attitude and smooth way with words,” a press release reads.
The quality that hip-hoppers seem to find most enviable in Original Sinatra is his air of stylish menace, and in particular, one much-touted association. “It’s always good to compare yourself to people you look up to,” Jay-Z told a Swedish TV interviewer last year. “Pretty much the way he lived his life and the parallels in how he affected the culture is what I strive to do.”
“You also, both of you, had a tough background,” the interviewer said.
“Yeah,” Jay-Z replied, smiling. “His was a little tougher than mine — the Mob.”
In fact, Jay-Z (né Shawn Carter), 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. 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.
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.”
As Frank’s fame grew, his swagger turned bolder. He was a short, slight man, hypersensitive and brilliant, and an Italian-American in an era when that ethnic group was low in the social order. As a young entertainment phenomenon in the early and mid-’40s, Sinatra was a kind of proto-hip-hopper: he strutted around Manhattan and then Hollywood with a pre-Rat Pack posse (known as the Varsity) of hangers-on high and low: songwriters, comedians, former boxers. He loved bling — he is said to have given away $50,000 worth of gold cigarette cases and lighters before he turned 30. He lived his life precisely as he pleased; consequences were for others to worry about.
Still, the engine of Sinatra’s fame, what really makes him endure, is the contradiction at the heart of this tough-seeming genius: his exquisite way with great American popular songs. He could always — still can — make you feel he is revealing emotional truths to you and you alone. He worked enormously hard on the technical aspects of singing that facilitated this impression: breath control, diction, deep study of the lyric.
But ultimately, his vulnerability is at the core of his magic. There was an operatic intensity to Frank Sinatra’s existence. His life mistakes were legion; he was, always, at the mercy of powerfully oscillating emotions. The conflicts filter into the molecules of his music. We hear, we respond.
Rap, of course, would seem to be about outer rather than inner conflict: swagger and defiance don’t just set the tone, they shout it. And yet the best rappers expose the sorrow and humanity that underlie the swagger. Eminem’s hymn to recovery “Not Afraid” is both brutally self-critical and self-transcending, reaching out to listeners who’ve been down the same addictive path.
And Jay-Z’s “Empire State of Mind,” which begins by trumpeting the rapper’s importance to the big city, modulates to sympathy for those who get lost in it: wayward girls from small towns, ball players and rap stars hooked on Ecstasy and addicted to the limelight. When the Swedish interviewer asked Jay-Z, “What is your talent?” he answered shyly. “I guess, telling the truth in rhyme,” he said. “It’s all about emotion — the detail and emotions in the songs that I sing just connect to people all over.”
Frank Sinatra often said much the same thing, in slightly different words, about his own music. Still — obligatory compliments aside — he wasn’t apt to be generous about the music that followed. According to his former valet George Jacobs, Sinatra expressed his true feelings about rock one day in the mid-1960s, when the Doors’ “Light My Fire” came on the car radio for the umpteenth time: He reared back and kicked the radio with the heel of his shoe. Now, that’s gangsta.
James Kaplan, the author of Frank: The Voice.