“He’s a dead man,” the talent agent Irving “Swifty” Lazar declared of Frank Sinatra in 1952. “Even Jesus couldn’t get resurrected in this town.” Maybe not, but Frank Sinatra could. Literally overnight—after the Academy Awards ceremony on March 25, 1954, where he won best actor in a supporting role for From Here to Eternity—Sinatra brought off the greatest comeback in show-business history. And he had done it all in Hollywood, a ruthlessly Darwinian company town that reviles losers but has the sappiest of soft spots for a happy ending. His Oscar underlined the fact that he was also a freshly viable recording artist with a new contract at Capitol Records, where he and a brilliant young arranger named Nelson Riddle had begun creating the string of groundbreaking recordings that would revolutionize popular music in the 1950s.

Now, like a king returned from exile, Frank took the world’s measure and saw that it was good. He entered into a frenzy of personal and professional activity that would scarcely let up for the next dozen years. Sinatra not only won an Academy Award in 1954, he had his biggest hit record in eight years, “Young at Heart.” He went into the recording studio 19 times in 1954, and laid down 37 tracks. He shot three movies. He played two two-week stands at the Sands in June and November, and did three weeks at the Copacabana over Christmas and New Years. He was on the radio constantly: There was his twice-a-week, 15-minute show To Be Perfectly Frank; his weekly, semi-tongue-in-cheek detective series Rocky Fortune (he would quickly tire of the program, a less than dignified vestige of his hard-luck days, and wind it up in March); and later in the year, a series for Bobbi Home Permanents called The Frank Sinatra Show.

He worked hard, too, at distracting himself from Ava Gardner, who had married him in 1951, but quickly tired of their mutual combustibility—not to mention his seemingly bottomless career slide. Three years on, Ava was living as an expatriate, cohabiting in Spain with the charismatic Luis Miguel Dominguín, the darkly handsome bullfighter whose rivalry with his brother-in-law Antonio Ordoñez would later inspire Ernest Hemingway’s long Life magazine piece “The Dangerous Summer.” She would soon file for divorce from Frank.

Frank hadn’t been much more than a boy when he married his first wife, Nancy Barbato, in 1939, and though he may have behaved like a bachelor throughout his 12-year first marriage, he hadn’t been this free in a long time. In 1954 he would be linked romantically with, among others, the French actress Gaby Bruyere, the Swedish actress Anita Ekberg, and the American actresses Joan Tyler, Norma Eberhardt, Havis Davenport, and (perhaps) Marilyn Monroe. He also kept company with the singer Jill Corey and the heiress and would-be actress Gloria Vanderbilt. There were probably numerous others, including, problematically, the not quite 16-year-old Natalie Wood.

Still, the most important emotional connection in Frank Sinatra’s life at this time was the one between him and his new arranger at Capitol, the sublimely gifted Nelson Riddle. The two had first struck gold together in April of 1953, after Capitol vice-president and creative head Alan Livingston, who felt Sinatra needed the kind of new sound that his previous arranger Axel Stordahl was unable to provide, cleverly introduced Riddle, in the guise of a substitute conductor. Sinatra had had no idea who Riddle was before their first recording session, but the moment he heard the playback of the Riddle-arranged “I’ve Got the World on a String,” he knew his life had been altered as irrevocably as it had been the first time he laid eyes on Ava Gardner. This was the thunderbolt, musically speaking.

Frank Sinatra had met his musical match. Though Riddle hadn’t had anything like Frank’s early success—he played third trombone for Tommy Dorsey after Sinatra’s departure—the serious-minded New Jerseyan, who grew up in Ridgewood, about 20 miles from Frank’s hometown of Hoboken, seems to have had, from the beginning, a head full of complex music and a deep ambition to hear it played and sung. In contrast to his bandmates, who spent most of their off hours boozing and trying to get laid, Riddle devoted much of his spare time to listening to Ravel and Debussy on his portable record player.

As a young and unheralded arranger in the late 1940s and early 50s, Riddle managed to eke out a living by ghostwriting charts for busier, more established colleagues. He was known inside the business for being able to turn out orchestrations in hours that would take others days; he was so adept at imitating the styles of others that as a ghost, he was truly invisible.

The lushly romantic Jacques Ibert composition “Escales”—“Ports of Call,” in English—was one of his holy grails. As was “Stomp It Off,” arranged by the great Melvin “Sy” Oliver, for the Jimmie Lunceford big band. The common thread between the two compositions was sex—slow and sensual, in the case of the Ibert; rock ’n’ roll, with the Oliver. Riddle was a sensualist with the demeanor of a scientist. And not a happy scientist. “Dad had a sadness about him,” Riddle’s daughter Rosemary Riddle Acerra recalls. “It was just this somber, serious mood. He was always thinking.” Julie Andrews, who worked with Riddle on her TV variety series in the 1970s, called him Eeyore.

Two major subjects were inextricably intertwined in his mind. Once, during a marital spat, Riddle’s wife Doreen accused him of only thinking about music and sex. The arranger later remarked to his son, with the glimmer of a smile, “After all, what else is there?” Riddle wrote, of his work with Sinatra, “Most of our best numbers were in what I call the tempo of the heartbeat…. Music to me is sex—it’s all tied up somehow, and the rhythm of sex is the heartbeat.”

He went on: “In working out arrangements for Frank, I suppose I stuck to two main rules. First, find the peak of the song and build the whole arrangement to that peak, pacing it as he paces himself vocally. Second, when he’s moving, get the hell out of the way…. After all, what arranger in the world would try to fight against Sinatra’s voice? Give the singer room to breathe. When the singer rests, then there’s a chance to write a fill that might be heard.”

He had learned this lesson painfully, on an aborted early session with Frank: Partway into a take of “Wrap Your Troubles in Dreams,” Sinatra stopped the band and called Riddle into the recording booth, explaining heatedly to his ambitious young arranger (Nelson was five and a half years Frank’s junior) that he was crowding the singer out, having simply written too many notes, beautiful as the notes might have been. Riddle never made the mistake again.

It was a critical moment. Sinatra, who was capable of firing associates at the drop of a Cavanagh fedora, could easily have axed Riddle then and there. But Frank was musically acute enough to realize that Riddle was taking him in new and daring directions: The arranger just needed a little guidance in the art of orchestrating for Sinatra. “Nelson was smart because he put the electricity up above Frank,” Quincy Jones once said, “and gave Frank the room downstairs for his voice to shine, rather than building big lush parts that were in the same register as his voice.”

“Dad evolved, with Frank’s help, and some of his own,” Rosemary Riddle Acerra says. “I think Frank was very astute and generous.” At the same time, she says, her father was very clear about why he was there: not, like so many around Sinatra, as a mere employee, a hanger-on, or a supplicant, but as a musical collaborator of the first order. “Dad wanted to work with Frank because he saw something very special,” Acerra says.

Sinatra and Riddle’s first major collaboration, Swing Easy!, had artistic energy in abundance. The album, released in August of 1954, was sheer grace—Riddle’s spare and gleaming up-tempo arrangements brought out Sinatra at the very peak of his art and emotional complexity. It was to be a long peak. His voice had ripened from the boyish tenor of his 1940s Columbia days to a baritone with a faint husk—from violin to cello, in a famous formulation attributed to both Riddle and Sammy Cahn—and the voice had become rich with knowledge. That knowledge contained much sadness. If Ava Gardner had been Delilah to Frank’s Samson while they were together, she would be his muse for years after they broke up—specifically and crucially, the great Capitol years. “Ava taught him how to sing a torch song,” Riddle said. “She taught him the hard way.”

Two years later, the Sinatra-Riddle collaboration would reach its high-water mark, with a session that is now considered the pinnacle of Frank Sinatra’s recording career—a career that spanned the years from 1939 to 1995 and produced 112 Billboard-charting singles and 23 gold or platinum albums.

Frank carried the sheer exuberance of the previous two years with him into KHJ Radio Studios on Melrose Avenue in Los Angeles on Monday night, January 9, 1956, when he arrived to record four songs with Riddle for the album that would become Songs for Swingin’ Lovers! The exclamation point was a fitting punctuation for Sinatra’s life at that moment. He was clicking on all cylinders—making great records, turning in memorable movie performances, earning serious money. *Time’*s August 29, 1955, cover story on him had estimated his income for that year at “something close to $1,000,000”—an astronomical number in the mid-1950s. The old days—the bad, poor days—were a blip in the rearview mirror. Swingin’ was the operative word.

He usually strolled into Studio A, upstairs at KHJ, at about 8 P.M., and always with an entourage: In this period the group would have consisted of Jimmy Van Heusen (one of whose songs would be recorded on the night of January 9); friend, music publisher, manager, and sometime bodyguard Hank Sanicola; Don McGuire, who was directing Frank during the day in the Western Johnny Concho; a prizefighter or two; sundry members of the Holmby Hills Rat Pack, such as Humphrey Bogart and Lauren Bacall, Judy Garland, and Rodeo Drive restaurateur Mike Romanoff; and the blonde or brunette of the moment. The atmosphere tended to crackle with excitement. “There was always a crowd at those Sinatra sessions on Melrose,” the trombonist Milt Bernhart recalled.

They should have charged admission! Because the studio had been a radio theater, it had an auditorium. And the place was packed to the back. You weren’t just playing a record date, you were playing a performance. They took a great chance on the people applauding, because they could get caught up in the thing, and ruin a take … but believe me, they were sitting on the edge. And it was an “in” crowd: movie stars, disc jockeys. It was big, big…. It was hard to get in, you had to be invited. But they’d fill the damn place!

For Nelson Riddle the anticipation was less pleasurable. “At a Sinatra session the air was usually loaded with electricity,” he remembered. But:

The thoughts that raced through my head were hardly ones to calm the nerves. On the contrary—questions such as: “Will he like the arrangement?” and “Is the tempo comfortable for him?” were soon answered. If he didn’t make any reference to the arrangement, chances are it was acceptable. And as far as the tempo was concerned, he often set that with a crisp snap of his fingers or a characteristic rhythmic hunching of his shoulders.

The tempo that January night was upbeat, in keeping with the album’s preplanned scheme. Continuing the prescient model he had initiated at Columbia with 1946’s The Voice of Frank Sinatra, Frank organized each of his Capitol albums around a specific mood or mode: downbeat or upbeat, ballads or swingers. The term “concept album” wouldn’t be coined until much later, but Sinatra invented the idea, and it was Riddle who helped him perfect it. More than ever, with Songs for Swingin’ Lovers! he was far more than just a singer: He was an artist shaping his medium.

The one slower-paced number Frank recorded that night, Andy Razaf and Eubie Blake’s “Memories of You,” didn’t make it onto the album. The other three songs on the roster were Sammy Fain, Irving Kahal, and Pierre Norman’s “You Brought a New Kind of Love to Me,” Johnny Mercer and Van Heusen’s “I Thought About You,” and Mack Gordon and Josef Myrow’s “You Make Me Feel So Young,” a song that had debuted, without much of a splash, in the 1946 musical film Three Little Girls in Blue. Riddle and Sinatra were about to turn it into an instant classic.

Songs for Swingin’ Lovers! was dance music of the hippest kind: swinging, infectious, supremely listenable. Rock ’n’ roll may have been on its way in—1956 was the year it would land like a falling grand piano—but its appeal at first was merely visceral and primitive. Sinatra and Riddle had visceral and sophisticated locked up in a way that would last.

The key lay in the hand-in-glove development of Sinatra as a singer and Riddle as an arranger. It wasn’t just that Frank’s voice had deepened; it had also toughened, through time, heartbreak, cigarettes, and liquor. “I didn’t care for his original voice,” Riddle once said. “I thought it was far too syrupy. I prefer to hear the rather angular person come through…. To me his voice only became interesting during the time when I started to work with him…. He became a fascinating interpreter of lyrics, and actually he could practically have talked the thing for me and it would have been all right.”

Interestingly, Sinatra had recently been quoted in Walter Winchell’s column as saying, “Everything I learned I owe to Mabel Mercer.” He was speaking of the trailblazing vocalist who began as an idiosyncratic chanteuse of the American popular song and eventually became a virtual diseuse, sitting in an armchair onstage and literally speaking the lyrics to piano accompaniment. Audiences hung on every syllable.

“I’ve always believed that the written word is first, always first,” Sinatra once said. “Not belittling the music behind me, it’s really only a curtain… you must look at the lyric, and understand it.” But of course there was more to it than that. “During the Capitol period,” Charles L. Granata writes, Sinatra “began to take more noticeable liberties with the rhythm and timing of his vocal lines.”

The conductor Leonard Slatkin—both of whose parents played on the Songs for Swingin’ Lovers! sessions—said, “Imagine that you’re delivering a sentence in a particular cadence, a particular rhythm, where the strong syllables come on strong beats and the weak syllables come on weak ones. When you listen to Sinatra’s songs, even ones that are highly rhythmically charged, you’ll find that often he’ll delay that strong syllable. It may not occur right on the downbeat. It will be just that fraction late, giving a little more punch to the word itself. I’m sure he thought about it. I’m sure that this was not just improvisatory on his part.”

It wasn’t. “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 stodgy. 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.”

His delivery was now at its zenith. Listen to Sinatra’s version of “You Make Me Feel So Young” on Songs for Swingin’ Lovers!, and you hear a great singer in joyous command of every component of his art—voice, tempo, lyrical understanding, expression. It is (imagine the seats in the radio theater, packed with rapt listeners) simply a magnificent performance. It is also a perfect union of singer, arrangement, and musicians.

The secret eminence behind it all was Tommy Dorsey. Three powerful forces had come together in 1939 when the great bandleader hired the brilliant arranger Sy Oliver and then lured Frank Sinatra away from the Harry James orchestra. Oliver wrote charts that wedded strings to horns in a new and powerful way, and a Dorsey signature sound was born.

Sinatra mainly sang ballads when he was with Dorsey; still, he had ears—great ears—and he heard what Oliver could do with an up-tempo number. A couple of years after Frank went out on his own, Nelson Riddle joined the Dorsey band. Riddle was only a so-so trombone player, but as a budding arranger, he took careful note of Oliver’s writing. When it came time to write up-tempo charts for Sinatra, Riddle brought along not only his deep grounding in the complex orchestral textures of the French Impressionist composers but also the big-band chops he shared with Sinatra.

“In planning Songs for Swingin’ Lovers!”—which Riddle called “perhaps the most successful album I did with Frank Sinatra”—“Frank commented on ‘sustained strings’ as part of the background to be used,” the arranger wrote.

The strings, by observing crescendos in the right places, add to the pace and tension of such writing without getting in the way. It was a further embroidery on this basic idea to add the bass trombone (George Roberts) plus the unmistakably insinuating fills of Harry “Sweets” Edison on Harmon-muted trumpet. I wish that all effective formulas could be arrived at so simply….

The musicians assembled on the stage in Studio A were truly a starry group, an amalgam of some of the finest classical string players and jazz instrumentalists around: Frank demanded no less. Besides Eleanor and Felix Slatkin, a cellist and Sinatra’s concertmaster respectively; bass trombonist George Roberts; and minimalist trumpeter Sweets Edison, the orchestra included trumpeter Zeke Zarchy, another Dorsey alumnus; the great Duke Ellington valve trombonist Juan Tizol (who was also the composer of “Caravan” and “Perdido”); alto saxophonist Harry Klee, who doubled on flute (he can be heard swinging beautifully on the outro of “Feel So Young”); and Sinatra’s musical right hand, pianist Bill Miller.

And then there was the sad-eyed trombonist with a jutting lower lip, Milt Bernhart, who, as the Songs for Swingin’ Lovers! sessions continued, would play a crucial role in the most famous song Frank Sinatra ever recorded, “I’ve Got You Under My Skin.”

As Frank Sinatra Jr. tells the story, his father had finished the second recording session of the week in the early hours of Wednesday, January 11, 1956, and planned to go to his house in Palm Springs first thing on Thursday. The final Songs for Swingin’ Lovers! session was set for Monday the 16th, and Frank wanted to rest up over the weekend.

Instead, producer Voyle Gilmore called him at one A.M. on Wednesday and said that, because the album looked to be a big seller, Capitol vice-president Alan Livingston had made an executive decision to put three more songs onto the 12-inch LP. This would necessitate an extra recording session on Thursday the 12th. Frank was not pleased.

He phoned Riddle at home, waking him up, and told him that he had to arrange three more songs, immediately. “Sinatra gave him three songs real fast. Either he had them already written down or he pulled them out of a hat,” Frank Jr. said. He went on:

Nelson got out of bed and started writing. By seven o’clock the next morning he got two songs to the copyist. He then had a few hours’ sleep and started writing again at about one o’clock in the afternoon. Nelson knew that “you-know-who” wasn’t going to be a very happy person that night because he did not want to be working…. With [Riddle’s wife] Doreen at the wheel of their station wagon, Nelson was in the back seat finishing the arrangement while holding a flashlight.

Rosemary Riddle-Acerra notes that her father used a leaf from the dining-room table as a laptop desk.

When the Riddles arrived at KHJ Studios on the evening of the 12th, according to Frank Jr., Vern Yocum, the copyist, had several of his associates there. Sinatra recorded the first two tunes —“It Happened in Monterey” and “Swingin’ Down the Lane”— with Nelson and the orchestra while the copyists were writing down the last arrangement. Frank then shifted gears and, with a chorus, recorded a single called “Flowers Mean Forgiveness.” Then he returned to the album, with Cole Porter’s “I’ve Got You Under My Skin.”

Sinatra’s usual method with Riddle when planning out arrangements was to sketch out ideas verbally—“make it sound like Puccini”; “give me some Brahms in bar eight”—while Nelson took rapid notes. All this usually happened well in advance of recording. In this case, with one day’s notice, Frank told Riddle, about “I’ve Got You Under My Skin”: “I want a long crescendo.”

“I don’t think he was aware of the way I was going to achieve that crescendo,” Riddle later said, “but he wanted an instrumental interlude that would be exciting and carry the orchestra up and then come on down where he would finish out the arrangement vocally.”

The arranger’s mind turned immediately to one of his masters, Maurice Ravel, and the French composer’s great and sensuous ballet, Boléro. Riddle has written of the piece’s “absolutely tantalizing slow addition of instruments to this long, long crescendo, which is really the message of Boléro…. [I]t is excruciating in its deliberately slow addition of pressure. Now that’s sex in a piece of music.”

His rough idea was to write a chart with an Afro-Cuban flavor—the mambo movement was then at its height, with Cuban bandleaders like Perez Prado, Machito, and the Spanish-born, Cuban-trained Xavier Cugat in the forefront—but with the clock ticking, Riddle was stuck. He phoned George Roberts for advice. “Why don’t you steal the pattern out of Kenton’s ‘23 Degrees North, 82 Degrees West?’ ” the trombonist, an alumnus of Stan Kenton’s big band, said.

Kenton’s band had been incorporating Latin influences into its performances since the mid-1940s; the title of his 1952 hit “23 Degrees North” referred to the map coordinates of Cuba. Nelson didn’t steal the pattern, but he got the message. He wrote a long, sexy crescendo for Roberts’s bass trombone and the string section, and at the bridge—the song’s middle section—sketched out eight bars of chord symbols for trombonist (and fellow Kenton alumnus) Milt Bernhart to use as a framework. Bernhart’s solo itself was to be totally improvised, and it would have to be good.

“I’ve Got You Under My Skin” was the last song Sinatra recorded on the night of January 12, which means that by the time the tape started rolling, the clock may have ticked over into the early hours of Friday the 13th. First, though, the band ran through the number once while Frank stood in the control booth with Riddle, producer Voyle Gilmore, and recording engineer John Palladino. Sinatra was listening carefully, making sure the recording balances were correct and the arrangement sounded right. Riddle’s heart was in his throat. Though he had dashed off the chart under maximum pressure, he knew Frank expected nothing less than greatness. “There’s only one person in this world I’m afraid of,” Riddle once confided to George Roberts. “Not physically—but afraid of nonetheless. It’s Frank, because you can’t tell what he’s going to do. One minute he’ll be fine, but he can change very fast.”

When the run-through was finished, though, the battle-scarred studio musicians stood as one and gave Riddle a warm ovation, “probably because somebody knew that he wrote it in a hurry,” Bill Miller recalled. Years later, in an interview with Riddle, Jonathan Schwartz asked him if he hadn’t said to himself about the arrangement, “This is awfully good.” “No, I probably said, ‘Wow, isn’t it nice that I finished it in time,’ ” Nelson answered.

But Frank knew it was awfully good. Though he was usually One-Take Charlie on movie sets, in the recording studio he would spend as much time as necessary to get a song right. Still, Milt Bernhart recalled, “it was unusual that he would have to go past four or five takes.” Accordingly, “I left the best stuff I played on the first five takes,” Bernhart said. But, the trombonist remembered, Sinatra knew that something special was happening.

Frank kept saying, “Let’s do another.” This was unusual for Sinatra! I was about ready to collapse—I was running out of gas! Then, toward the tenth take or so, someone in the booth said, “We didn’t get enough bass… could we get the trombone nearer to a microphone?” I mean, what had they been doing? There was a mike there for the brass, up on a very high riser. “Can you get up to that one?” they asked. And I said, “Well, no—I’m not that tall.” So they went looking for a box, and I don’t know where he found one, but none other than Frank Sinatra went and got a box, and brought it over for me to stand on! Eleven takes, twelve, thirteen—some of them would have been false starts, only seconds long, but some went longer, until Frank raised a hand, shaking his head, stopping the music and telling the band and the control booth what had to change. Then, take 22. “Milt perspired a lot to start with,” recalls guitarist Bob Bain, who played on the session. Now the trombonist was soaked through. “He looked at me and said, ‘I don’t have another one left.’ ”

Yet Frank was in high gear, ready to push forward into the 22nd take. And Nelson, on the podium, was ready to propel the musicians to the peak of their art. Sinatra and Riddle’s string of great albums together would continue unbroken through 1957’s A Swingin’ Affair! But later that year, most shockingly to Riddle, Frank turned to another arranger, Gordon Jenkins, for the moody LP Where Are You? Sinatra would return to Nelson again and again, for such important Capitol albums as Close to You, A Swingin’ Affair!, Frank Sinatra Sings for Only the Lonely, and Nice ’ n’ Easy—and then, at Frank’s own label, Reprise, for several more LPs, including The Concert Sinatra and Strangers in the Night. But from the late 50s through the end of his recording career, Frank Sinatra’s restless artistic temperament continually drove him to seek new sounds: Besides Jenkins, he would employ many other gifted arrangers, including Billy May, Johnny Mandel, Quincy Jones, Neal Hefti, Don Costa, and Claus Ogerman, drawing from each a unique musical palette.

Frank’s restlessness—in his art, his personal relations, in everything—was his genius and his illness, and a permanent condition. There was always the dark undertow—the inner voices that told him that underneath it all he was nothing and nobody, a little street guinea from Hoboken. The furies that would frequently blind him when his vulnerabilities were touched. The terrible impatience—with the incompetence and stupidity that were so rife in the world, with things he needed to happen instantaneously, and so rarely did. The realization that he was like nobody else, and therefore destined to be alone. His terrors: of aloneness itself; of sleep, the cousin to death. And always, always, the vast and ravening appetites.

His impatience and simple need for movement—in his career and in his emotional life— frequently trumped good sense. He would have seen from the beginning how deep his musical bond—and yes, therefore his emotional bond—with Nelson Riddle was, and some part of him may have resisted it. Riddle, a shy man who was in awe of Sinatra as both a musician and a star, would not, could not, have pressed the issue. And so just as he constantly looked for new lovers, Frank sought (and would continue to seek) other arrangers, even as some part of him must have known Riddle could give him all he needed, and more.

Even so, their work together extended to the 1980s; Nelson wrote the arrangement of George Harrison’s “Something” heard on 1980’s Trilogy, the three-disc package that also included “Theme From New York, New York,” Sinatra’s last Top 40 hit. But there were misunderstandings and recriminations—mostly on the part of the moody and sensitive arranger—and their last truly great extended collaboration was 1966’s Strangers in the Night. The album (arranged by Riddle except for the title track, which was orchestrated by Ernie Freeman) was a knockout. Besides the title song, which was a massive hit (though Frank hated it—“He thought it was about two fags in a bar!” said Joe Smith, the head of Warner-Reprise), the LP contained the sublime “Summer Wind” and a gorgeous, Hammond organ-driven update of Sinatra’s 1943 hit “All or Nothing at All.” Strangers in the Night would hit No. 1 and stay on the charts for 73 weeks, Frank’s biggest LP success since Only the Lonely in 1958.

Yet when it was all said and done, Sinatra decided the Riddle era, as great as it had been, was history. “There is no particular story, and if there is one, I don’t know it,” Riddle told the NPR interviewer Robert Windeler not long before his death, at age 64, in 1985.

[Sinatra] is not inhibited by any particular loyalty…. He had to think of Frank. I was hurt by it, I felt bad, but I think I was dimly aware that nothing is forever. A different wave of music had come in, and I was closely associated with him in a certain [other] type of music…. So he moved into other areas. It’s almost like one changes one’s clothes. I saw him do it with Axel Stordahl, my favorite; I should have realized that it would be my turn. He just moved on.

Take 22. “I’ve Got You Under My Skin” starts at a lope, in 2/4 time, with a baritone sax or bass clarinet playing the now-famous repeating figure—bum-ba-dum-BOM ba-dum-BOM ba-dum-BOM—in the background. Despite the lateness of the hour and the number of takes, despite the number of unfiltered Camels he has smoked that day, Sinatra, under that Cavanagh fedora, is singing as easily and bell-clearly into the Neumann U47 microphone as if he had just stepped out of the shower and taken it into his mind to do a little Cole Porter. Perhaps, now and then, as he loses himself in the great song and the sound of the great band around him, he closes his eyes. The heavenly strings and the bright brass interplay effortlessly behind the first and second choruses, and then, as Frank caresses the last lines of the bridge —

But each time that I do,
just the thought of you
Makes me stop before I begin,
’Cause I’ve got you under my skin….

—Roberts and the strings lift the long crescendo higher and higher and higher until it seems they can go no higher. And then Milt Bernhart, drawing on reserves he didn’t know he possessed, goes wild on his slide trombone, simply blowing his lungs out. It is to Sinatra’s immense credit that his powerful final chorus, driving the song home, is as strong in its own right as Bernhart’s historic solo.

It was a wrap.

“After the session, I was packing up, Frank stuck his head out of the booth, and said, ‘Why don’t you come in the booth and listen to it?’ ” the trombonist recalled.

So I did—and there was a chick in there, a pretty blonde, and she was positively beaming. He said to me, “Listen!” That was special! You know, it never really went past that. He never has been much for slathering around empty praise. He just doesn’t throw it around very easily. If you weren’t able to play like that, then why would they have called you? You knew that you were there—we all were there—at Frank’s behest. Rarely, if ever, would he directly point something out in the studio.

Another time, Bernhart remembered, Sinatra praised French horn player Vince DeRosa on executing a difficult passage by telling the band, “I wish you guys could have heard Vince DeRosa last night—I could have hit him in the mouth!”

“We all knew what he meant—he had loved it!” Bernhart said. “And believe me, he reserved comments like that only for special occasions. You see, it was very hard for him to say, ‘It was the greatest thing I ever heard…’ But that’s Sinatra. He could sing with the grace of a poet, but when he’s talking to you, it’s Jersey!”

As for his favorite arranger, Sinatra’s esteem was far greater than Riddle ever knew. The story goes that on their 1955 collaboration, In the Wee Small Hours—counted by many as one of the greatest albums ever made by any artist—Frank was so thrilled with Riddle’s arrangement of Cole Porter’s “What Is This Thing Called Love” that after he had finally satisfied himself with a perfect vocal, he turned to the somber arranger and said, “Nelson, you’re a gas!” It was Sinatra’s highest form of praise.

There was a pause while the socially awkward Riddle came up with the best answer he could think of. “Likewise,” he said.

Adapted from SINATRA: THE CHAIRMAN, by James Kaplan, to be published in October 2015 by Doubleday, an imprint of the Knopf Doubleday Publishing Group, a division of Penguin Random House LLC; © 2015 by the author.

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