According to the Power Thesaurus, there are 1284 synonyms for the word “intensity,” and you could use almost any of them to describe Frank Sinatra.

One of Frank Sinatra’s most admirable qualities was his refusal to do anything half-assed. People who knew him often used the words “perfectionist” and “obsessive” to describe him, but those adjectives present a one-sided picture implying an ultimately positive result. It’s equally true that when Frank Sinatra fucked up, he totally fucked up. Reading his life story leads one to conclude that he was sent here on a mission to experience as much of life as he could at the highest possible level of intensity, good times and bad times alike.

Sinatra biographies tend to be far too gossipy for my tastes, and my first reaction when finishing one is to congratulate myself on never having had the slightest urge to become famous. The less personal reaction is sheer exhaustion. Sinatra was the human soul painted in colors so vivid and textures so rich that it’s almost impossible to believe that all the stories that make up his life narrative happened to one person, but they did. He experienced the pinnacle of success and the bottom of the barrel. He won an Oscar, eleven Grammies, three stars on the Hollywood Walk of Fame and a Presidential Medal of Freedom; he also attempted suicide more than once.

The years 1949-1953 represented a period politely referred to as a “career slump,” when a combination of questionable choices and terrible publicity resulted in a severe decline in his popularity and the ultimate loss of his recording contract. At one point he was so broke he had to borrow $200K from his record company to pay back taxes. During this period he also experienced the death of his close friend and publicist, divorce from his first wife Nancy and almost immediate remarriage to Ava Gardner. Those are a lot of high-stress life events to pack into such a short period, so it’s no wonder that his career temporarily wound up in the crapper. But true to the words he would sing thirteen years later, “Each time I find myself flat on my face/I pick myself up and get back in the race.” Capitol Records took a flyer on Sinatra and signed him to a seven-year deal in early 1953; a few months later, From Here to Eternity would fill movie palaces all across the nation and Sinatra would be rewarded for his efforts with the Oscar for Best Supporting Actor the following year. 1954 also saw the release of his first two albums for Capitol (Songs for Young Lovers and Swing Easy!), both of which were warmly received. In his first two years with Capitol, Sinatra released no less than eight Top 20 singles, indicating that all was forgiven as far as the listening audience was concerned.

The move to Capitol was critically important for two reasons. Capitol allowed Sinatra an unusual amount of artistic freedom in contrast to the more restrictive environment at Columbia, and he would now emerge as a man with a clear and expansive vision of the music he wanted to produce. Equally important was the pairing of Sinatra with Nelson Riddle, as magical a connection as The Beatles and George Martin. The two had worked together on his first two Capitol albums, which allowed Riddle to accustom himself to Sinatra’s unrelenting intensity and gave Sinatra a partner who could transform his intuitive and insightful visions into the series of truly remarkable musical arrangements you hear on In the Wee Small Hours.

In the Wee Small Hours is recognized as a concept album, one of the first attempts by an artist to use the long-playing format to explore a single, unified theme. The theme here is “lost love,” the mood is intensely introspective, and the guy only gets the girl in his wildest fantasies. It has been referred to by insiders as “the Ava album” because Sinatra was still grieving over the failure of his tumultuous marriage to Ava Gardner. I don’t doubt the veracity of that assertion, but in terms of evaluating the artistic merit of In the Wee Small Hours, the backstory is a completely irrelevant distraction. The responsibility of the artist is to transform personal experience into universal experience, to move beyond self-absorption and express through art those aspects of individual experience that are shared by the other members of the human race. Loss of one’s partner is a sadly common human experience, but too many attempts to capture the essence of that experience cross the line into sentimental, boo-hoo, poor-me self-pity. What is remarkable about In the Wee Small Hours is how Sinatra and Riddle combine to create the purest expression of loss without intervening noise, making it possible for the listener to experience catharsis concerning their own encounters with lost love. This is accomplished through Riddle’s sensitive and responsive arrangements and Frank Sinatra’s remarkable command of voice and lyrics, a hard-won skill that allowed him to transform songs into vivid, memorable human stories.

“In the Wee Small Hours of the Morning” opens the album, and the first instrument you hear is a celeste, a signal that we are about to enter a world of quiet reflection marked by feelings both tender and sad. Once the lush strings complete the opening passage and Sinatra steps up to the mike, you notice how the arrangement places Sinatra’s voice firmly in the front and center of the monaural soundscape. Sinatra insisted on supporting arrangements that gave him plenty of room to maneuver, and, as Riddle himself would admit, Sinatra consistently came up with the best approach for a given song. Here the string arrangement reflects a sense of tenuous stillness occasionally interrupted by bursts of emotion, indicating a restless sleep. The arrangement thoroughly complements Sinatra’s interpretation as he rides the shifting moods of reflection and emotion with perfect execution. He delivers the first verse in a rich but restrained voice, adding a touch of tiredness to his delivery to reinforce the mood of a troubled late night. When he reaches the second verse, Sinatra expresses the emotions welling up inside through perfect phrasing and build; when he reaches the crucial phrase “if only,” he extends the notes and increases his volume so effectively that you can picture his formerly supine body twisting and turning in the darkness. He delivers the last line of the verse in a tone combining mournful regret and utter helplessness, so much so that you genuinely feel for the man:

When your lonely heart has learned its lesson
You’d be hers if only she would call
In the wee small hours of the morning
That’s the time you miss her most of all

The verse is repeated as the song comes to a close, and Sinatra delivers that last line with a subtly quivering vibrato that feels like he would cry himself to sleep if he weren’t so tired. The song ends with a gentle repetition of the melody on the celeste, as if someone has tiptoed into the room and covered his tired body with a blanket. A three-minute masterpiece of song arrangement, “In the Wee Small Hours of the Morning” is also a masterclass in the vocal arts (as are many of the songs on this album).

Sinatra’s approach to Ellington’s “Mood Indigo” is best appreciated by comparing it to the Ellington version that appears on Masterpieces by Ellington. Ellington didn’t choose Yvonne Luanauze (real name Eve Duke) as the band’s vocalist because she was a great singer, but because her mellow timbre was similar to the sound of a saxophone. Ellington’s focus was on the gestalt of an arrangement, how various sounds and timbres blend into a coherent whole. The vocals on “Sophisticated Lady” and “Mood Indigo” sync perfectly with the band, but Luanauze’s rendering of the lyrics does little to excite the emotions. Having experienced several bouts of what we would call “clinical depression” during his down years, Frank Sinatra had first-hand experience with deep indigo moods and their terrifying power. What I key into are his two completely different approaches to the “no, no, no” lines, which in the context of the song are response lines to an invisible colleague who claims to have a bad case of the blues. In the first set Sinatra remains faithful to the notes on the page but varies his tone on the second and third notes to say, “Man, you don’t know how bad it can get” in a faintly shaken tone as he momentarily relives the awful experience of the deep blues. In the second go-round, with the smaller supporting cast of musicians doing their best to mimic a big band sound, Sinatra extends the negative to a dozen repetitions, clearly telling his listener that he doesn’t have the slightest fucking idea what he’s talking about. Neither rendition crosses the line into “my pain is greater than your pain,” instead coming across as friendly advice from a guy who has real-life experience in the depths of darkness. While I love the ambiance Ellington creates in his version, Sinatra’s interpretation feels more true to life.

“Glad to Be Unhappy” is a Rodgers and Hart number that didn’t exactly set the world on fire back in 1936 and was largely forgotten until Sinatra rescued it from oblivion. The introduction of celeste and bass is but a brief nod to thematic considerations, as Sinatra changes the mood in the introductory verses by delivering a semi-stern lecture to the face in the mirror, urging himself to accept fact over fantasy when it comes to love. When he shifts from near-monotone to a mini-crescendo to dramatize the cinematic fantasy implied by the lyrics, “Look at yourself, do you still believe the rumor/That romance is simply grand?” my heart just melts, especially with the elegant, elongated delivery of that oh-so-sophisticated word, “grand.” Once the introduction is complete, the song shifts to a downtempo jazz combo number with a somewhat elaborate melody, modified slightly by Sinatra to sync with his read of the lyrics. Sinatra was never one to simply accept a score or lyrics as-is; his quest for perfection would not allow him to indulge in an off-the-shelf interpretation. Since he couldn’t read music in the conventional sense (but could follow the patterns on lead sheets), the lyrics served as his interpretational foundation. “I’ve always believed that the written word is first, always first,” he said. “Not belittling the music behind me, it’s really only a curtain. You must look at the lyric and understand it. Find out where you want to accent something, where you want to use a soft tone. The word actually dictates to you in a song, it really tells you what it needs.” That quote from James Kaplan’s The Chairman speaks volumes, for it highlights his unique ability to approach a song in a more organic fashion, where his choices to vary tone, syncopate, clip or elongate are firmly rooted in the human tale expressed in the lyrics.

“I Get Along Without You Very Well” is a Hoagy Carmichael number that has morphed into something of a jazz standard despite (or because of) its melodic origins in Chopin’s Fantaisie-impromptu in C sharp minor, Op 66. Since most classical music was written long before the first international copyright agreement in 1886, the great composers have provided many a songwriter with royalty-free opportunities to snatch a promising melody. A good way to prepare yourself for Sinatra’s interpretation is to first listen to Chet Baker’s take on Chet Baker Sings, which, oddly enough, is a more straightforward rendering of the piece. Sinatra’s version features gorgeous, interlocking interplay between strings and voice, as if the strings are responding to the tenor of Sinatra’s voice. That voice covers a lot of territory on the scale, and Sinatra’s voice is particularly beautiful on the elongated high notes.

My favorite song on In the Wee Small Hours is the least politically correct number on the album, as it celebrates the virtues of smoking cigarettes to facilitate self-reflection. This was, of course, normal behavior in the 1950s, as seen in many movies and television programs of the era. Characters would take a break from the action to have a smoke and reflect on the plot line, or light up at the kitchen table when they needed to work out a particularly thorny problem. Smoking was also something of an art form, as demonstrated by Rita Hayworth’s memorable door-opening scene in Gilda. Unlike today, where smoking almost automatically identifies a character as an evil villain, both good guys and bad guys smoked, and while sinister meanings were occasionally attached to a female character who puffed on a Lucky, female smoking had the titillation factor going for it, which served to neutralize any ill will a viewer may have felt. Since I always disclose the biases of which I am aware, I will happily admit that I smoke cigarettes and couldn’t give a fuck what people think.

Written by long-time Sinatra pal Jimmy Van Heusen in conjunction with lyricist Eddie DeLange, “Deep in a Dream” conjures up the figure of a man who has dimmed the lights and lit a cigarette as he considers his lost love:

I dim all the lights and I sink in my chair
The smoke from my cigarette climbs through the air
The walls of my room fade away in the blue
And I’m deep in a dream of you

Riddle balances the strings with horns and an occasional fluttering flute to illustrate the multiple moods in this piece, an innovative score that responds immediately to Sinatra’s emotions. Sinatra begins the verses in the lower part of the register, moving smoothly through the melodic peaks of the third line before descending to the lows to close the verse and enter the dream world. Like clouds in the sky, smoke moves in mysterious ways, with strands turning into shapes that resemble objects in the real world. The modern instinct in responding to the second verse would be to say, “Wow! This would make one seriously cool music video,” but really folks, your imagination will work just fine:

The smoke makes a stairway for you to descend
You come to my arms, may this bliss never end
For we’ll love anew just as we used to do
When I’m deep in a dream of you

I imagine the woman in a sparkling, shape-fitting gown, perfectly coiffed with long curled tresses falling on her bare shoulders . . . but since my image of “love anew” is too kinky for the reading audience, I’ll let you fill in the rest of the blanks. Sinatra’s voice intensifies with excitement in this verse, sweetening the word “bliss” with a combination of joy and relief. In the bridge, he imagines music coming from the ceiling and the couple does what all couples did in the good old days when they heard music—they dance! Alas, this beautiful scene cannot last forever,  and the whole thing . . . goes up in . . . smoke (sorry):

My cigarette burns me, I wake with a start
My hand isn’t hurt, but there’s pain in my heart
Awake or asleep, ev’ry mem’ry I’ll keep
Deep in a dream of you

Riddle inserts a brief horn response to the phrase “wake with a start,” reflecting that “What? What the hell? Where am I?” moment when our slumber is cruelly interrupted. On the final “of you,” Sinatra plummets to the lowest note he can handle, his voice quivering slightly in response to the stretch, but miraculously coming back full force when he is free to rise to the more comfortable note above, which he holds for a healthy stretch in the fade. Sinatra’s breath control was legendary, a skill developed through hard work and supported by frequent morning swims in the ocean, and not harmed in the least by his consistent consumption of Camels . . . so there! “Deep in a Dream” is an imaginative demonstration of the virtues of poetic economy, beautifully delivered by a master storyteller and supported by an equally masterful arranger.

The fantasizing continues with “I See Your Face Before Me,” which begins with a lovely swirl of flute, woodwinds and strings creating a dream-like environment. This piece tends to favor Riddle’s Fantasia-reminiscent arrangement over Sinatra’s vocal, which makes sense when you consider it was the first song Nelson Riddle arranged, way back in 1938. Still, Sinatra is marvelous, smoothly and sensitively guiding the song with a tone of wondrous attachment to the lovely vision that refuses to vacate his consciousness.

The firmly-strummed Spanish guitar that opens “Can’t We Be Friends” gives Sinatra a cue to ramp up the assertiveness level, and he delivers the opening line, “I took each word she said as gospel truth” as if he’s sharing his frustration with a buddy over a Jack Daniels (3 rocks, two fingers) at Toots Shor’s. He then descends to the bottom of his range to confess his own stupidity: “The way a silly little child would.” The intro leads into a soft jazz arrangement featuring George Van Eps on guitar and Paul Smith on celeste; meanwhile, Sinatra plays the part of a chump to perfection, keeping his voice a touch on the ragged side to express a sense of emotional exhaustion. The verses repeat the lyrical story in different words (I believed her, what a dope), but my favorite is the last verse with its more colloquial language:

I thought I’d found the gal I could trust
What a bust, this is how the story ends
She’s gonna turn me down and say
“Can’t we be just friends ?”

“Just friends” and the antidote “cold shower” go back a long way; the song originally appeared in a 1929 musical. However, the “Can’t we be friends” routine is not exclusively limited to male victims, as Ella Fitzgerald confirmed in her covers of the song (one solo, one with Satchmo). The difference is in the response: a cold shower may cool off a ready-to-explode penis, but it only makes our nipples harder.

Whether it was due to self-induced tension or a triggering memory of Ava Gardner, Sinatra broke down crying after the master take of “When Your Lover Has Gone.” The song itself has an unusual structure with an intro and two short verses that contain a relatively weak refrain, but Sinatra cared more about lyrics than structure, and it’s easy to imagine him falling apart after delivering that last brief verse:

What lonely hours, the evening shadows bring
What lonely hours, with memories lingering
Like faded flowers, life can’t mean anything
When your lover has gone.

Riddle pauses the background music for a split-second before the verse to give Sinatra some space, and when you hear his voice emerge from the silence, you notice it is filled with emotion he can barely contain. He lingers over each word, as if considering the meaning of each one . . . “lonely” . . . “hours” . . . “memories” . . . until he launches into the crescendo of the third line, his voice rising in volume and pitch, in a tone that sounds as if he is resisting every move forward to avoid having to accept the truth in the cold closing line: “When your lover is gone.” This is clearly one of Sinatra’s most powerful performances, and his ability to maintain musical discipline while recalling deeply painful memories is the mark of the ultimate professional. In the hands of most singers, this song would easily turn into a melodrama; with Sinatra, it is a noble, cathartic tragedy.

Side Two opens with what I consider to be one of Cole Porter’s weaker numbers, “What Is This Thing Called Love?” I’m definitely in the minority here, as the song has been recorded again and again by everybody who is anybody, but the absence of wit and wordplay that characterized Porter’s more mature works creates too much of an obstacle for me to overcome. Sinatra almost deconstructs the song by slowing the tempo considerably; most of the versions I’ve heard (Ella, Red Garland, Clifford Brown and Max Roach) are fast and snappy. Riddle intensifies the question mark in the song’s title through a clarinet that sounds perfectly film noir, and Sinatra’s tone is one of genuine wonderment. I’m also not particularly fond of “Last Night When We Were Young,” one of Judy Garland’s favorites, but I’ll give Sinatra and Riddle credit for making the song far more interesting with a marvelous build leading to Sinatra’s climactic held note.

The celeste returns for “I’ll Be Around,” where Sinatra places himself in the role of noble hanger-on, and despite his reputation as a tough guy, he approaches the part with perfect humility. Even when the song gives him several chances to overdramatize a held note, he restrains himself, making the lines “Perhaps you’ll see/You were meant for ME” all the more poignant. Though I can’t get my head around the concept of waiting around for someone who obviously doesn’t want you simply because YOU have decided she’s the one for you, I’ll exercise the same restraint Sinatra did and tell you that his version of “I’ll Be Around” is both charming and well-acted.

In my research for this review, I stumbled across an article on Vail Jazz titled, “Was Sinatra a jazz singer?” The author answered the question strongly in the affirmative, but I was surprised to learn that the issue was in doubt. Of course he was! And one of the best! Having already solidified his jazz cred here with “Mood Indigo,” he gets another chance to demonstrate his chops in “Ill Wind,” a Harold Arlen jazz classic first performed at the Cotton Club in 1934. Riddle sets the stage by using woodwinds to create a sense of dark mystery, cueing Sinatra to intensify the mood through blue notes and off-beat phrasing. His mood oscillates between vulnerability and mustered strength, coloring the song in hues of deepest blue. Harry Edison from the Count Basie Orchestra delivers a trumpet solo that could have served as the theme music for the album cover, capturing that late-night loneliness after all your best lines and generosity with the booze have failed to pierce the hearts of the opposite sex and now you’re too broke to call a taxi.

We’re now presented with back-to-back Rodgers and Hart numbers, the first featuring Sinatra in the role of oblivious mate. “It Never Entered My Mind” features an elegant, restrained arrangement featuring French horns, flute and strings. Sinatra sounds like a man who is stunned to find himself alone, but the most interesting aspect of the song is his interpretation of the bridge:

You had what I lack myself,
Now I even have to scratch my back myself.

Most versions deliver the lines straight, imbuing the words with a semi-humorous veneer. Sinatra takes that second line and turns it into something richer: the moment where the guy finally and fully understands that he is now utterly alone:

Now I even have to scratch my back . . . . . . . myself.

That long pause speaks volumes, as does the tortuous delivery that precedes it. With one brilliant phrasing decision, Sinatra transforms the song into an indictment of routine in relationships and a moment of hard revelation . . . a striking example of his ability to discern the subtext behind the lyrics.

Instead of a woman gliding gracefully down a smoky stairway, we now encounter a woman dancing on the ceiling in defiance of the laws of gravity. Despite the scientific absurdity, “Dancing on the Ceiling” is a delightful little number with a suitably whimsical arrangement integrating celeste, piano and guitar. Sinatra is in fine form, singing on and off the beat, shaping the placement of the lyrics to the feel of the song and displaying again his thoroughly remarkable breath control. On the last line of the bridge, he holds the note on “there” through the first line of the last verse without a discernible drop in power or expressiveness in his delivery. I’d use the word “breathtaking” to describe that passage, but that would qualify as the worst pun I’ve ever written, so I’ll slip into advocacy mode and urge every singer in any genre to study Frank Sinatra’s vocal techniques.

The one song where I think Riddle’s arrangement is off is “I’ll Never Be the Same,” a song that began life as an instrumental with the cutesy-wutesy title “Little Buttercup” but morphed into something heavier once Gus Kahn added the lyrics. The problem I have with the arrangement is the use of the flute, and coming from someone who’s been blowing flutes (and other long hard instruments) since she was eight (make that fourteen for other long hard instruments), that’s what I call a pretty damning indictment! Specifically, the flute flurries here call up images of pleasant spring days when butterflies and birds glide over the warming breeze. Unfortunately, the lyrics describe a dark existential crisis where the narrator observes “And when the songbirds that sing/Tell me it’s spring/I can’t believe their song.” 86 the goddamn flutes and give me a goddamn cello! Sinatra tries his best to make it work, but even great singers lack the power to overcome an out-of-sync arrangement that contradicts the main storyline.

The closing track finds Sinatra revisiting a tune he recorded with Tommy Dorsey and the Pied Pipers back in 1941, “This Love of Mine.” This is the only song on In the Wee Small Hours where Sinatra receives songwriting credit, having written the lyrics. The song was definitely in need of a refresh, as the original reveals a rather stiff Sinatra who still had a long way to go to master syncopation and conversational phrasing: he hits all the notes, on time, in sync, and oh my, the result is really, really boring. Fortunately for history, Frank Sinatra was a lifelong learner dedicated to continuous self-improvement:

“Syncopation in music is important, of course, particularly if it’s a rhythm song,” Sinatra said. “It can’t be ‘one-two-three-four/one-two-three-four’ because it becomes story. So, syncopation enters the scene, and it’s ‘one-two,’ then maybe a little delay, and then ‘three,’ and then another longer delay, and then ‘four.’ It all has to do with delivery.”

—excerpt from The Chairman by James Kaplan

In the updated version, Sinatra’s phrasing is more relaxed, reflective and natural, giving the lyrics far more weight than was apparent in his rather formal recital in the original. The most noticeable difference can be found in the delivery of the line, “Since nothing matters, let it break” (referring to his heart). In the original, the pause indicated by the comma is just that: a short break in the flow before Sinatra sings the notes on time like a good boy should. In the revised version, the comma turns into an incredibly long ellipsis, amplifying the meaning of “let it break” to something stronger—more like “Let the world go to hell, I’m done.” There are numerous subtle differences between the two versions that demonstrate Sinatra’s progress from apprentice to master, and re-recording this number must have been an ironically triumphant moment for him—ironic because it took fourteen years and too many failed relationships for Sinatra to grasp the real meaning of the words he had written.

Riddle’s arrangement here is as perfect as perfect gets, a supportive background dominated by rich, tempered strings with a touch of celeste. In a masterstroke, Riddle ends the song that ends the album with the instrument that introduced the album: the celeste. What we hear is a rising figure that seems to fade naturally, like the sound of wind chimes, reinforcing the musical and emotional themes while adding a gentle reminder of the transitory nature of human feelings and human life.

In the Wee Small Hours ushered in a period where Sinatra could do no wrong, collaborating with Riddle to produce a string of universally acknowledged masterpieces of the vocal arts. After a brief pause in the action during his transition from musician-under-contract to record company mogul, Sinatra would hit another peak period in the mid-60s with different collaborators (including daughter Nancy). He continued recording and performing well into the 1990s, constantly refusing to roll up into a big ball and die.

In my promo tweet for this review, I described Sinatra as “the most American singer of them all.” I said that because his life story embodies the full range of the American experience, and the contradictions in his personality are uniquely American. He was the Horatio Alger hero, the guy from Hoboken with no connections who worked his way to the top—and sometimes his legendary ambition led him to step on others to get what he wanted. His equally legendary temper led him to respond violently to provocations—but he was also one of the first to celebrate diversity in song and to use his privilege and influence to demand that Vegas hotels and restaurants serve black customers. At the beginning of the 1950’s he existed in the living hell of depression and with the embarrassment of commercial failure—but by the end of the decade, he was the top recording artist in the world and a major box office star. Frank Sinatra was the ultimate rugged individualist who could never quite get rid of the chip on his shoulder, but he balanced that with a strong streak of generosity and a willingness to help others who were getting screwed by the system. He loved hard, hated hard, partied hard and worked hard. He was the personification of intensity.

Individualism, competitiveness, generosity, the drive for success, the violent tendencies, the rise, the fall, the comeback—Sinatra was a man who integrated American myths and many of the characteristics of the American hero into his personality. But what makes In the Wee Small Hours so very special in addition to its beautiful arrangements and stunning vocals is that Frank Sinatra had the courage to shatter one of those myths: the myth that boys don’t cry, the myth that men dare not display vulnerability or weakness. The truly great Americans were people who broke boundaries, and through a combination of emotional honesty, artistic excellence and a vision of the possibilities inherent in the long-play format, Frank Sinatra broke cultural and artistic boundaries with In the Wee Small Hours.

Americans! If you’re going to celebrate anything on the Fourth of July, celebrate Frank Sinatra, a truly great American.