Friday 11 December 2015

Book Review: "Why Sinatra Matters" by Pete Hamill

The cover of Hamill's book

Frank Sinatra was born on December 12th., 1915 in Hoboken, New Jersey. Today would have been his hundredth birthday — he died in May, 1998 at the age of 82. To mark the centenary of Sinatra's birth, Little Brown and Company has re-released Pete Hamill's excellent book Why Sinatra Matters. Originally released in November 1998 — just six months after the singer's death — the book became an American bestseller. This new version, published in October, includes a new introduction by the author in honour of Sinatra's centenary.

It took me a long time to appreciate the work of Frank Sinatra. When you're a kid you tend to be narrow-minded in your musical appreciation. Sinatra was just uncool. Through most of the 1960s (my teenage years) my love of pop music was focused on the British "beat-groups". I knew a bit about the American rock-and-rollers who had inspired bands like The Beatles, The Rolling Stones and The Who. But their music was almost a decade-old; it sounded strange and dated to a youngster — the popular music of a different generation. And as far as the swing-jazz and crooning on the 40s went, well that was ancient stuff that only old people could enjoy. 

I did hear Sinatra quite often on BBC Radio in the 60s — especially on request programmes like Two-Way Family Favourites and Housewives' Choice. BBC Radio and TV back then really was "broadcasting"; granted, there were programmes that focused on specific types of music, but on many shows you could expect to hear all sorts of popular music. And Frank Sinatra was very popular ... with the old folk!

"... Strangers in the night, exchanging glances ... "

But the few Sinatra songs that did break through in that decade were not that impressive to my ears. There was "Strangers in the Night" in 1966. It was a #1 hit — his first in 11 years. But it sounded quite trite to me. It amazed me to learn much later that Frank agreed. He actually thought that it was "a piece of shit ... the worst fucking song that I ever heard." Maybe that recording's "doo-be-doo-be doo" coda wasn't playful scatting, after all; maybe it was a dig at the fatuousness of the lyrics?

And at the very end of the decade came Sinatra's 1969 recording of "My Way" — originally a French pop song, but now the tune was matched to a Paul Anka lyric. This was even worse than "Strangers in the Night". Again, Frank agreed. Later he would sometimes tell audiences, "I hate this song." Despite a common misconception that the lyrics sum up nicely Sinatra's personal approach to life, this bombastic song does not reflect the man's rather humble view of his art — regardless of his often boorish behaviour. Until he had this song pushed at him — against his better instincts — as the chance for a big hit, he would not have dreamed of singing such a conceited hymn of self-celebration.

Yeah, I know, I didn't really hear much of his stuff, but the little that I did hear, I didn't like. Case closed. Ah, the sure arrogance of youth!

And on into the 70s, Sinatra and his Rat Pack buddies seemed to represent to us youngsters the worst sort of reactionary Hollywood entertainers; they always seemed to be in a Las Vegas casino — the belly of the beast. Misogynists, it seemed. Republicans for Nixon. The worst kind of show-biz dinosaurs. Enemies of Woodstock Nation; the antithesis of the progressive counter-culture.

Unlikely meeting of unlike minds: Frank and Elvis on TV together

Oh, and then there was his diatribe against rock-'n'-roll, sometime in the late 50s (before he started singing Beatles songs in the late 60s): "Rock n Roll is the most brutal, ugly, desperate, vicious form of expression it has been my misfortune to hear." Not too cool for the hordes of people who happened to groove to the likes of Chuck Berry, Jerry Lee Lewis and Elvis.

And so it went. Sinatra's career went into a slow decline. He did some duet recordings with current pop stars. And then he died in 1998. Guess what song they played over and over on the radio and TV obituaries? Right ... "My Way".

Always well-dressed — the snazzy Frank, invariably in a hat

But about five years after Frank died I started to listen to a lot more jazz and jazz singers: Louis Armstrong, Billie Holiday, Ella Fitzgerald, Sarah Vaughan. I was hearing more and more about Sinatra's Capitol recordings of the 1950s, mostly arranged and conducted by Nelson Riddle. These were the fruits, I read, of his great comeback. He was thought to be dead-and-gone as a popular entertainer by the late-40s. Then he won an academy award for his role in the film From Here to Eternity in 1953. And late that same year he began a long series of successful collaborations with Nelson Riddle.

The first album of theirs I dipped into was In the Wee Small Hours (1955). What a revelation that was. A superb album. I would listen to the whole thing over and over on my long commutes to and from work. A wonderful set of songs that were beautifully arranged and impeccably sung. This was not the Frank Sinatra I was familiar with. Not the man I thought I knew. Perhaps it was the languor of its approach — its elegiac mood, its melancholic tone. By this time in the mid-50s Frank was no longer the pop idol of hysterical "bobby soxers", he was now, apparently, the spokesman for middle-aged male sentimentality! He still had that magic vocal technique, but it was now employed on more interesting, more mature material. Within a couple of years I had most of Sinatra's 1950s albums in my collection!

Hamill's book — Why Sinatra Matters — is not a straight biography. It is organised chronologically: following some introductory material — which includes a reminiscence of an evening Hamill spent in 1970 with Sinatra in a New York saloon — this small book then proceeds with five chapters charting his career chronologically by focusing on one important element of the story in each chapter. It's an Interesting technique — the story moves thematically and chronologically at the same time. The book tells you a lot about Frank's life, but biographical detail is not the point — Why Sinatra Matters is really an extended rumination on how the key facts of Sinatra's life made him who he was as both a personality and a performing artist.

Chapter 2, for example, deals with the bigotry Sinatra faced because of his Italian-American ancestry. His grandmother's family, the Garaventes, came from Genoa. His grandfather's family, the Sinatras hailed from a village near Palermo in Sicily. These grandparents immigrated to the U.S. in the 1890s with two young children who would eventually meet in Hoboken, get married, and parent Francis Albert "Frank" Sinatra. 

With Nancy, his first wife, in Hoboken, New Jersey (mid-30s)

His grandparents' move to the U.S. was part of a huge influx of European immigrants in the 35 years leading up to WWI; from 1880-1915 about 24 million crossed the Atlantic  — about 4.5 million of those were Italians. Most of the Italians came from the land-exhausted rural areas of the south, especially Sicily. The majority of this uneducated group were illiterate — not only did they not know virtually a word of English, they couldn't read or write Italian either. This made it very difficult for them to get good jobs — they had to settle for manual labour and other non-skilled occupations.

Frank as a kid in Hoboken

The majority of these Italian immigrants had to settle for a low — if not the lowest — position on the social ladder. They clung to much of la via vecchia (the old way), the traditional values and customs of their home country, primarily as a defense mechanism. Their children (first generation Americans), of course, quickly adopted la via nuova, (the new life) because of their exposure to American institutions and their immersion in American culture.

Frank (top, right) as a member of the Hoboken Four

For some easily-identifiable linguistic, religious and social reasons, Italian-Americans were one of the most discriminated against immigrant groups. This prejudice, of course, extended into the entertainment industry. Many musicians, singers, and actors of Italian-American extraction changed their names, in order to get ahead. Dean Martin was born Dino Crocetti; Connie Stevens was Concetta Ingoglia; and Tony Bennett began life as Anthony Benedetto. Frank Sinatra had been advised on several occasions to do the same. When he joined the Harry James Orchestra in 1939, James tried to persuade Frank to become Frank Satin. "I said no way, baby," Sinatra recalled years later; "The name is Sinatra. Frank fucking Sinatra."

Frank resented the terrible bigotry imposed on the Italian-American community. It made him angry; and he went out of his way to fight back against it. In fact, his early experiences of prejudice against his own community made him stand up later against bigotry wherever he faced it. He went out of his way to promote the interests of Afro-American musicians, for example, and he defended them against discrimination. 

Frank and Ella performing together on TV

The third chapter in Hamill's book deals with the theme of loneliness. Sinatra was an only child — an unusual thing within the Italian community. Furthermore, during his childhood he was often neglected emotionally. His father was aloof; and his mother was often out of the house pursuing her own interests and projects. Natalina Sinatra (née Garaventa) was a real go-getter. She was full of schemes and ambitions, working for many years as an operative for the Democratic Party within her own community in Hoboken. Frank endured long periods of solitude as a young child, and that must have fuelled his fantasies of fame and fortune. There was a private and sensitive side to his character, despite that tough and supremely self-confident swagger he usually showed.

Loneliness, argues Hamill, is the key theme of his life and work. The sense of abandonment — especially of love gone wrong — got stronger as the years went by. Melancholic songs of loss and thwarted dreams lie at the heart of his greatest recordings in the 1950s. He had an intense, ardent and doomed relationship with Ava Gardiner for most of the 50s; and the emotional strain of that failed romance drives much of the song-selections of that decade.

Recording for Capitol in the 50s

But the prime reason, of course, why Sinatra matters — beyond the attitude and the themes of his work — is because of the brilliance of his vocal technique. During the height of Sinatramania in the early 1940s, Frank was often dubbed "Swoonatra" because of the ardent, often hysterical, behaviour of his young female fans ("bobby soxers"). Later in his career he was often known either as "The Chairman of the Board" — he had started his own record label (Reprise) in 1960 — or as "Ol' Blue Eyes". But the tag that stuck the most, and the one that is clearly the most appropriate, is "The Voice".

Almost from the very beginning, Sinatra's singing voice was something special. He began singing professionally in 1935. The bandleader Harry James heard him singing on a New York radio station in 1939 and signed him to front his orchestra. From there Sinatra's career quickly took off. He had only been with them for about six months, when Sinatra joined — with James's blessing — the Tommy Dorsey Orchestra. He stayed with Dorsey for three years; in September 1942 he managed to wangle himself out of his contract to go solo. Not only that, he also manage to persuade the orchestra's musical arranger, Axel Stordahl, to go with him (promising to pay him five times the salary that Dorsey did). Dorsey never forgave Sinatra for his effrontery.

Sinatra fronting the Harry James Band (1939)

What is so special about the singing of Sinatra, The Voice? As Hamill summarizes it: "it was a combination of voice, diction, attitude and taste in music that produced the Sinatra sound". The voice, as with most singers, evolved over time: as Hamill so aptly puts it "from a violin to a viola to a cello, with a rich middle register and dark bottom tones." 

In his everyday conversation, Sinatra used lots of slang and lingo. He could be very coarse — favouring the profane and crude argot of the streets. But when he was singing his diction was impeccable. He always sounded the consonants at the end of words, and you can hear every word in a lyric. Nothing is slurred, mumbled, or mangled. Sinatra once talked about his deliberate efforts to improve his speech. He used the example of movie stars to inspire him. With these changes, he recalled, "I started becoming, in some strange way, bilingual. I talked one kind of English with my friends. Alone in my room, I'd keep practising the other kind of English."

When Frank sang an upbeat, sunny lyric, you could hear an appropriate lightness of feeling in his approach; when he sang a melancholy song, you could the sadness in his voice. He effortlessly moulded his vocal instrument to match the meaning of a song. As Hamill points out, he also learnt how to add tenderness into his performance while remaining manly. He was one of the first Americans to perfect the Tender Tough Guy persona.

Sinatra learnt two very important things from his time with the Tommy Dorsey Orchestra. The first was the way that Dorsey prepared a show as though it was one long piece of music — as though it was a carefully thought out album. [This was in an era before the long-playing album was born.] It was all dance music, but Dorsey planned it so that it proceeded with different moods and movements towards a crescendo. Sinatra applied the same technique to the concept albums he recorded for Capitol records in the 1950s. When he was working with Nelson Riddle, he would make a list of the 14, or so, songs he wanted to record for a particular album. Riddle would then prepare the musical arrangements. Everything would be in place once the recording began in the studio.

Sinatra singing with the Tommy Dorsey Orchestra (early 40s)

The other lesson Sinatra learnt from Dorsey was how to breathe. Dorsey was a trombone player with incredible breath control. He could release air slowly enough to support long lyrical melodic lines. Indeed, he was able to tie the end of one musical phrase into the start of the next. Sinatra used the same technique with his singing. To improve his breath control, he would spend a lot of time in swimming pools — especially under water. He developed a distinctive legato sound, delivering the lyrics of a song in long, uninterrupted lines. His perfect phrasing matched lines and half-lines in order to bring out the sense of the song's lyric — perfect storytelling.

Telling a story — Frank studies a song lyric in between takes

Effective communication of the lyrics in a song was crucial for Frank. He always studied them carefully in the studio, right before a take. There are several photographs of Sinatra with the sheet music spread out in front of him. They seem to encapsulate perfectly his ability to grasp fully the meaning and emotion in a song. He's not studying the music — he couldn't read music — he was reading through the lyrics. 

... much older, but still studying lyrics

Sinatra had an ability, like no other singer of his generation, to get inside a song. When he was ready to sing, he delivered it as though it were a short story. You couldn't help but get involved in his performance, following every nuance of his perfect phrasing. There are so many versions he did of oft-recorded songs that sound like they're the definitive one. He didn't just sing a song. He got inside it and delivered it as a dramatic performance. There are very few singers who can match him on this.

"One For My Baby (And One More For the Road)" by Harold Arlen and Johnny Mercer"

And, then, there is the matter of Sinatra's impeccable taste in songs. Before the concept of the "great American songbook" had been dreamt up, Sinatra had been busy constructing concept albums built on the very best songs written during the first four decades of the 20th century — songs by Irving Berlin, George Gershwin, Rodgers and Hart, Harold Arlen, Cole Porter, Jerome Kern, etc. Frank developed this taste very early — he spent long hours as a young singer listening to their work and memorizing the lyrics. In the many albums he recorded during his peak in the 1950s, it is very difficult to find a single dud or piece of filler.

Conferring with Nelson Riddle about an arrangement

Finally, a word about Sinatra's choice of arrangers and musical directors. As mentioned earlier, he worked effectively with Axel Stordahl in the 1940s. And, then, when he started recording albums for Capitol in 1953, he was lucky enough to hook up with arranger and bandleader Nelson Riddle. Between 1953 and 1981 they did an incredible 24 albums together. Sinatra's impeccable taste in material was evenly matched by Riddle's ability to create sympathetic and effective orchestrations. He spread solos creatively among woodwinds and brass, and he never made his string parts too lush and cloying. Nothing in his work sounds dated or annoying to the modern ear.

Why Sinatra Matters may be seen as a paean; but it's certainly not an uncritical hagiography or a defensive apologia. Hamill concedes that Sinatra was often cruel, crass, and obnoxious. He could be violent, too; and he had questionable ties to the Mob. On the other hand, as Hamill points out, much of the more serious accusations made against the man have never been substantiated and — even after years of close surveillance by the F.B.I. — he was never indicted. Much of the negative talk against Sinatra, it seems, was based on rumours spread by professional gossips in the entertainment trade and by journalists and pundits who disliked his don't-give-a-shit, take-no-prisoners attitude. The man did not believe in trying to ingratiate himself with anyone. "It's Sinatra's world," Dean Martin once quipped, "we just live in it."


This is a well-written, concise, and thoughtful inquiry into the career of Frank Sinatra. Sinatra was — as most great artists are — a man of contradictions. Many people are repelled by the more unsavoury aspects of his personality. But underneath that rough and often vulgar facade lay a man of great sensitivity and artistic talent. He worked hard to build that talent. And he listened carefully as he developed his musical technique. Frank Sinatra became the greatest practitioner of the American popular song. He made it an art form. Sit back and listen, for example, to the magic that Sinatra and Nelson Riddle create with In the Wee Small Hours or Only the Lonely, and you'll find yourself mesmerized by the wonderful material, the beautiful voice, the incredible technique, the gorgeous arrangements. Just perfect. And that's why Sinatra matters.

Pete Hamill (born June 24, 1935) is an American journalist, novelist, essayist, editor and educator. Widely traveled and having written on a broad range of topics, he is perhaps best known for his career as a New York City journalist.  Hamill was a columnist and editor for the New York Post and The New York Daily News.

Why Sinatra Matters by Pete Hamill amillH   was published by Little Brown and Company, New York in 1998. The new edition was released in October, 2015 to mark the centenary of Sinatra's birth. The book has 180 pages of text, 8 black-and-white, full-page photos between chapters, a list of recommended recordings, a brief bibliography of Sinatra books consulted, and a short list of recommended Sinatra movies.

The 1955 Capitol album: In the Wee Small Hours


  1. Frank Fucking Sinatra......I couldn't quite believe you taking up the cause on this one Clive BUUT i have to say, I certainly learned a few things from ur blog that shed a different light on the man and his music. Not to say that I am wholly convinced but I will give you this - you've persuaded me to get my hands on a few of his LPs and give them a listen (though I'm more likely to borrow copies from the library - or perhaps my parents library - first :) I'll report back to u on my explorations. Thanks for this! cheers

    1. "Not wholly convinced," but willing to give the man a listen. That's enough for me! As I mentioned in the piece, give "In the Wee Small Hours" or "Only the Lonely" several listens. Or try them both! I'd be very interested in your reaction.

      As always, thanks for your response.

  2. Even though his was not the music of my generation, I always enjoyed it. With the exception of those awful songs you mentioned from the 60s, of course! Great voice. He was a wonderful actor as well. Though older than my father, he rather resembled him, and that made me want to like him. But I just never liked him, couldn't get past that obnoxious Rat Pack stuff, mob connections, etc. I remember later hearing an aunt saying on more than one occasion that "Frank Sinatra is not a nice man." She had had some sort of interaction with him, or had observed him at close range, I can't quite remember the story. She gave no details but simply said, in measured tones, "Frank Sinatra is not a nice man." Back to his acting, if you have not seen The Manchurian Candidate (1962), you might find it interesting.

    1. Thanks for your response. There are plenty of people who fall under the heading of "not a nice man"; but that is no reason to ignore the greatness of their art. Bob Dylan, for example, is not a particularly engaging or sympathetic public figure, but his recorded work is magnificent.