Frank Sinatra – In the Wee Small Hours – Classic Music Review

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-absorbtion 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 in relation to their own personal 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 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 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 together 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 note to say, “Man, you really 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 ambience 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 1950’s, 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 a 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.

Shame me all you want, your health nazi invective will bounce harmlessly off my secure and comfortable psyche.

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 on 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 the fuck 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 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.

That’s why they invented vibrators!

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 personally 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 though 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” all the way 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 be both obvious and 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 story line.

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 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 himself 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-60’s with different collaborators (including daughter Nancy). He continued recording and performing well into the 1990’s, 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 intense.

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.

25 responses

  1. […] Frank Sinatra – In the Wee Small Hours […]

  2. Matheus Bezerra de Lima | Reply

    Capitol’s executives thought that it was a risky decision to release an album full of sad songs. One of the legacies of the album is helping change cultural stereotypes that “men don’t cry, men are tough and don’t suffer because of love”. Historically, torch songs about lost love have been more associated with women. Sinatra showed in the album that men can allow themselves to be vulnerable, to display their sadness, to emotionally suffer and to cry without losing any bit of their masculinity.

    I also think the album evolved from the song “Last Night When We Were Young. All songs in the album were recorded in four sessions in February and March of 1955. With the exception of “Last Night When We Were Young”, recorded in March 1954! There are no known reasons for this very odd fact.

    But I think that a very likely reason is that the song might have been originally intended as a single, but eventually deemed by someone (maybe the Capitol’s executives, maybe Sinatra himself) too sad and uncommercial to be released as such. So, Sinatra (who had already toyed with the idea of an album that has some level of cohesion and is not just a random collection of songs in his Columbia album The Voice Of Frank Sinatra) probably decided to make a whole album of sad songs to fit the song. The recording session of the song was one that he was very passional and participative about. Over 30 takes, Sinatra was very perfectionist and focused on the smallest details of it. So, I can’t see Sinatra happy in throwing out of the window such an amazing recording that he loved and worked so hard to make it truly perfect. This is my whole guess of what happened.

  3. Matheus Bezerra de Lima | Reply

    I would love to know what do you think about my review of In The Wee Small Hours! It’s in the link above!

    1. I read both reviews (Wee Small Hours and Swinging Lovers) and loved them both. I was particularly fascinated with the section on “Last Night When We Were Young” and how it was censored by the “music should be happy” crowd. Neil Young had a similar experience with On the Beach—the shirts thought it was too depressing and withheld its release for years. There’s no question in my mind that In the Wee Small Hours was one of the greatest acts of courage in modern music.

      1. Matheus Bezerra de Lima

        Huge thanks!

  4. Matheus Bezerra de Lima | Reply

    Only The Lonely, his other masterpiece of sad ballads, is completing 60 years in this month, it was originally released in September of 1958!
    A new deluxe edition is being released!

  5. Great article! Re-posted on twitter @trefology

  6. I’m a big fan of Horace Silver. I agree with your characterization of Horace Silver’s music and personality. I never got to see him pay, bu I met him briefly at a jazz club in LA some years ago. Someone pointed out that a little old guy with disheveled hair under a baseball cap was none other than Horace Silver. I went over to express my appreciation for his music, and he had the same smile as on the cover, and was very nice.

    1. That’s a beautiful story! It’s nice when musicians actually are who they appear to be—and not a little bit rare. I would have loved to meet him and talked piano until the wee hours, as I imagine him to be as generous a teacher as he was a musician.

  7. Matheus Bezerra de Lima | Reply

    I read also in a interview with James Kaplan that, generally, Sinatra only really felt genuine happiness and peace of spirit, inner peace, when he sung, and sung well also. Singing was really his best and main therapy, by far. In other contexts of his life, tough… Sinatra had tons of flaws as a human being, but he was a genuine, passionate lover of all great music and all great artists, a lover of great art and the emotional power that it has. Ralph Vaughan Williams was one of his favorites composers. I also read once that Nelson Riddle was “forced” by Sinatra to study more deeply about classical music, because Sinatra would often mention the names of classical composers to Riddle when saying how he wanted the arrangements to be. So, Riddle had to listen more classical music for being able to fully what Sinatra really wanted. Riddle also, as you said in this review, knew how to leave space for the singer to be the main star. He learned it the hard way. In one of his earliest recording sessions with Sinatra, Sinatra got angry with Nelson Riddle because he had written too many notes and was overshadowing the singer. Sinatra gave Riddle a second chance and he learned with his mistake. The truth is that Sinatra made Riddle even better and Riddle made Sinatra even better. As you said, Sinatra in Capitol almost always released a sad album followed by a happy album and all over again, without much middle ground. Only Songs For Young Lovers, Close To You, Come Fly With Me and Nice ‘N’ Easy are more balanced. Both of these albums, specially Nice ‘N’ Easy, Songs For Young Lovers and Close To You, recapture more of the “easy listening” (I hate this expression and what it often implies, tough), relaxed crooning style of his Columbia Years.

    I wonder how much being the only son (specially in a time when this was so rare) and also the prejudice for being son of italian immigrants in a violent neighborhood contributed to his more explosive personality and his admiration for the powerful mafia guys. Sinatra even trained boxing! Besides, his mother was pretty unpredictable. I think that Sinatra once said that he never knew when she was going to hug him or beat him. If I am not mistaken, according to James Kaplan, perhaps his most happy period in life was as a very young “boy” that had just signed with Harry James and Tommy Dorsey later, the young man with so many dreams, idealizations and pursuing them, with an uncertain, but exciting and promising future. In retrospect, Sinatra always remembered this period in his life with extreme fondness.

    Amazing review! Keep the great work!

  8. I will miss your reviews.

    1. I’ll still be writing reviews; I just won’t be covering American artists.

  9. I realized, reading your review, how much I have mined this record for underplayed gems – Glad to Be Unhappy, I See Your Face Before, Me, and Can’t We Be Friends, just to name three. I consider Only the Lonely to be Sinatra’s masterpiece (and Riddle’s) but Wee Small Hours is right up there. Music at its highest level.

    1. It really is music at the highest level. The care that went into the Sinatra-Riddle records was amazing.

    2. Matheus Bezerra de Lima | Reply

      These underplayed gems are really what Sinatra is about, not Strangers In The Night, My Way and New York, New York.

      1. I agree wholeheartedly. That’s why it took me until my 30s to get to Sinatra. My first impressions of him were from those aforementioned songs which seemed bombastic and corny to me. That said, even in his later years he still lived in the very center of the beat.

    3. Matheus Bezerra de Lima | Reply

      I recommend the full reading of the article of the link above, but the most crucial and interesting part of it is below:

      “If there’s any tragedy connected with the Sinatra legacy, it’s that these days Ol’ Blue Eyes tends to be remembered for the wrong material. People often think of the anthems My Way and New York, New York as Sinatra classics, when really they’re Sinatra at his worst. Poorly constructed, overwrought ditties, with the Chairman of the Board’s ageing, ragged voice stridently competing with orchestras so cacophonous he sounds as if he’s singing against an invading squadron of B-52 bombers.

      Sinatra’s best work was delicate and nuanced. In the Wee Small Hours remains his most fitting monument – it’s pop music at its most subtle and evocative and a lesson to aspiring pop stars that singing isn’t just about belting out vulgar curlicues of melisma, like every second Australian Idol contestant. The crucial thing is to vocalise like you mean it.

      Sinatra scholar Will Friedwald argues that Sinatra the artist ‘is the first guy to show that a tough guy can be vulnerable and intimate and express all these emotions and still be masculine. And nobody has been able to do that before, and nobody has been able to do that as well ever since’.”

      Sinatra did not like My Way and absolutely HATED Strangers In The Night with a passion. He often said in the shows how much he hated the song and only sung it because the public really wanted madly. He called it a piece of shit and one of the worst things that he had ever listened. He was not very gentle with My Way either. He only sung it because he did not want to disappoint the public. In a show, he joked saying: “either this is getting better or I am getting used to it”. Sinatra considered that the song’s main problem were the lyrics. He tought that the lyrics were too on-the-nose, lacked subtlety and come across as arrogant. Another time, he said before singing My Way, joking, that he was going to sing the official American National Anthem!

      But there is one great thing about Strangers In The Night: Scoby-doo’s creator listened to Strangers In The Night in a plane and got the name of Scoby-doo from the “dooby-dooby-dos” that Sinatra sings in the end of the recording. It was also Sinatra’s first number one single in Bilboard in over 10 years!

      1. Wow, great knowledge! I will check out that article.

  10. Matheus Bezerra de Lima | Reply

    I think that it must be acknowleged also how great the cover of this album actually is!

  11. Matheus Bezerra de Lima | Reply

    I could not have described Sinatra’s life and personality better than you did. I wonder if he was a bipolar. Nelson Riddle said that Sinatra was the only person that he was afraid of, because Sinatra’s mood could change really fast, he was totally unpredictable, extreme in his emotions, he could be a gentleman and cruel, and, as you said, it is hard to believe that all the amazing things that happened in his life, all of his actions, could actually happen to and be made by a single person, but they did. Sinatra, with all his extremes and intense way of living, defies any conventional wisdom that divides people between “good” and “bad”, Sinatra was a extremely complicated man, there are no easy answers about him. I think that Sinatra ultimately wanted happiness, inner peace, true loving people and friends, as we all want, but he did not have a clue in how to handle and control his feelings and actions towards other people, he had serious problems to build healthy, solid and long relationships with anybody, specially women. Ava Gardner was his biggest love, but it was a relationship impossible to ever work, much because Ava Gardner was as much of a emotionally extreme, authoritative, unpredictable and vengeful person as him, both hated to accept orders and were not willing to accept being contraried by any one without retorting back. Ava Gardner, tough, was able to overcome the end of their relationship better than Sinatra, that was still deeply traumatized by their divorce for many years.

    This album is, at least among his ballad albums, his masterpiece alongside Only The Lonely. Like you said, this album has still much of a meditative, calm and reflection mood. Why am I saying “still”? Because each one of his next ballad albums in Capitol, with exception of Close To You, would be progressively darker, gloomier and desperate, culminating with No One Cares, released in 1959, and it has to be one of the darkest, most depressing, suicide albums in the history of popular music, I am amazed by a popular artist daring to release an album as gloomy and dark as this one, totally uncommercial and exhausting. Even Sinatra’s voice had significantly changed compared to 1955. In the 1953-1956 period, Sinatra’s voice still retained significantly much of the original, honeyed and sweet, delicate timbre of his Columbia Years, his first four Capitol albums show this strongly, but more clearly Songs For Young Lovers and In The Wee Small Hours (In The Wee Small Hours Of The Morning, I Get Along Without You Very Well, When Your Lover Has Gone and Last Night When We Were Young are the songs that highlight much of his still present 40s voice the most clearly and notoriouly in this album). By the time that Sinatra had released No One Cares in 1959, his voice was significantly darker, rougher, deeper compared to In The Wee Small Hours. In The Wee Small Hours represents for me, alongside Songs For Young Lovers, the sweet spot, the perfect balance between his young, thinner, more lyrical and sweet timbre of the 40s with the added richness and deepness of a now “fuller”, more resonant voice. Singles as Rain, My One And Only Love, From Here To The Eternity, Young At Heart, I Could Have Told You (all of these recorded in 1953), Three Coins In The Fountain, Half As Lovely, You, My Love, Someone To Watch Over Me (all of these recorded in 1954), Fairy Tale and Weep They Will (both recorded in 1955) show all that I said here about his 1953-1955 voice in this period as being the sweet spot perfectly.

    One curious fact: Last Night When We Were Young was recorded nearly a full year before all the other songs in this album. It was an recording that had more than 30 takes and, according to Nelson Riddle, one of the recordings that Sinatra was more obsessed and actively involved, demanding, for example, the considerable slowing of the song and the celeste, if I am not mistaken. This recording session made Riddle said that Sinatra had voice to burn in this time. I love the dramatic crescendo towards the song’s ending and Harold Arlen considered it the best song that he had ever written. Maybe this song was too sad to be released as a single, but Sinatra did not want to throw away this great recording, so maybe this was the final push to make Sinatra decide to release a full album of sad songs. I like this theory.

    1. Thank you! The issue of bipolar disorder did cross my mind but I’m no psychologist and didn’t feel comfortable talking about an unverified diagnosis; the clinical depression aspect was obvious. The contrast between Wee Small Hours and Swinging Lovers can be looked at as “bipolar” or “incredible versatility,” but they’re both great albums.

      I think you’re spot on about his search for inner peace, which would explain his preference for listening to classical music when at home. I also think you’re right about the push to release an album of sad songs beginning with “Last Night We Were Young,” as it fits with his constant quest for perfection. And yes, it’s one of the coolest covers ever!

  12. Great post! In the Wee Small Hours is Sinatra’s greatest album by a significant margin. It truly captures, not only his inspired mastery of melodic interpretation, but also his essence; a man-child frozen in adolescence navigating adult heartbreak. This condition informed his best recordings throughout his career. When he veered from his true self, his records, even when commercially successful, come across as absurd.

    1. Thank you! “Frozen in adolescence” is a good description, and may explain part of his appeal: most adults, male and female, seem frozen in adolescence because they focus more on achieving success or pleasing other people instead of developing anything close to emotional intelligence. Through that lens, Sinatra was able to connect with . . . what was that Nixon thing . . . ah, yes, “The Silent Majority.”

      1. Matheus Bezerra de Lima

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