Frank Sinatra (1915–1998) has been part of America’s soundtrack for almost eighty years, having released his first single, “From the Bottom of My Heart,” in 1939, when he was the vocalist for the Harry James Orchestra. America’s other crooner of the century, Bing Crosby (1903–1977), pithily summed up Ol’ Blue Eyes’s pipes: “Sinatra is the kind of singer who comes along once in a lifetime — but why did it have to be my lifetime?”
It was always thus, and Sinatra continues to draw new fans, sometimes ones that are almost as bigger than life as he was: Aaron Judge hit a home run in game 2 of the 2018 American League Division Series, and after the Yankees closed out the victory the colossal right fielder strode past the Red Sox clubhouse with a boombox blaring Sinatra’s “New York, New York.”
In 1995 Sinatra turned eighty, and to mark the occasion the Voice’s inimitable jazz explicator Gary Giddins edited a twenty-page special on the Chairman of the Board. In a sidebar, Giddins lays out the stellar qualifications of the contributors he gathered to pay tribute to the musical legend, noting that most of them “earn all or part of their livelihoods as musicians. Steve Allen, who last wrote for the Voice in the early ’60s, is a man of parts who virtually invented the TV talk show and used the medium to introduce numerous musicians, from Bud Powell and Art Tatum to Elvis Presley and Aretha Franklin.” Indeed, Allen’s contribution doesn’t mince headlines, titled as it is “The Greatest Singer of Them All.” The former TV host is a little less direct about the vocalist’s personal shortcomings: “So — as regards Sinatra, are all the stories about his lifelong association with the most notorious Mafia murderers and social savages, the stories about semipsychotic rages, true? The answer to all such painful questions is, to some degree, yes.”
Giddins also gives a shout-out to Mary Cleere Haran as “the finest cabaret singer of her generation, and possibly the wittiest ever.” Haran (1952–2011) certainly could turn a phrase, whether on the stage or the page. Reviewing Frank’s turn as the lead in the 1957 film Pal Joey, Haran writes, “Sinatra was born to play Joey. In the stage version, Joey is a nightclub hoofer. He had to be — Gene Kelly originated the role. But a nightclub singer is a lot more sensible, and who better to fit that sleazy bill than Frank Sinatra? I always felt MGM was the wrong studio for him. It was too respectable, conventional, decorous, and polished for Frank’s street-fighter approach to performance.”
In his own piece, Giddins explores the boss of bosses’ emeritus standing: “Any other artist of Sinatra’s stature would be allowed to achieve octogenarian status without the smirks, though who else would raise as much fuss in the first place? Saul Bellow and Arthur Miller share his year of birth: will attention be paid? Probably nothing comparable to Dr. S. (honorary degree, Stevens Institute, 1985), who occupies the low, middle, and high ground of popcult, but eternally undermines his undoubted genius with an edgy kitsch that verges on self-parody and promotes skepticism. That he is subjected to bad jokes at an age when his footfalls should be muffled with rose petals may simply signify that he is no longer anyone to fear. For, puzzling as the fact may be to future generations, Sinatra is one entertainer who instilled a sense of fear in paying customers as well as paid attendants; not a fear of physical violence per se, though, yes, there have been a few such victims, but of a more general sort — fear of not qualifying for the vicarious ratpackery of the affluent society’s Peter Pan–on-testosterone club for middle-aged rakes.”
Here we present the entire twenty-page supplement, chockablock with still more witty contributions — Sinatra’s Top 10 songs, tales of trombone solos and seriously swinging jazz — as well as ads from the period, all testament to the enduring fascination we still have for the self-taught balladeer from Hoboken, New Jersey.