I’m a passionate fan of Frank Sinatra and I wanted to pay respect to a truly amazing man. Sinatra was born on December 12, 1915 in Hoboken New Jersey. He was a son of Italian immigrants, named Francis Albert Sinatra. His mother died in childbirth, and in 1910, the father named his son, “Francis Albert Sinatra” after an uncle he had never met. The boy was nicknamed “Frankie” because his initials were F.A.S., and “Sinatra” because his father had been in the Italian army in the Italian army. A few years later, his father became a singer, and Sinatra learned to play the trumpet, piano, and sing. By the age of 16, Sin

While it may seem like an exaggeration that Frank Sinatra has been the subject of more biographies than any other individual in history, his influence on pop culture, film and politics is undeniable. The most beloved crooner to ever wear a tuxedo, Sinatra was a complex artist whose personal life was as fascinating as his career.

In case you’re not familiar, Frank Sinatra was a famous singer and actor of the 20th century. A big part of his career was acting in films, and the star had some very talented friends who helped him prepare for the roles. One of those friends was Peter Lawford, who was the stepson of the famous actress and was the President of MGM Studios in Hollywood. Lawford would take Sinatra to the set and explain what was required of him in a scene. What Lawford neglected to mention, however, was that the scenes would be filmed from the point of view of someone else who would then play the part of the person who was doing the acting. He’d then show Sinatra how to act the part of the other

Nelson Riddle, a music arranger, helped Frank Sinatra get to the next level when he needed it.

Frank Sinatra had been the headliner at New York’s Copacabana since the end of March 1950, when he performed his final set on the nightclub’s stage late on April 26. Only approximately 70 patrons remained, accounting for less than 10% of the Copa’s capacity. Sinatra opened his mouth to sing at 2 a.m., but nothing came out. He later said, “It’s only dust.” His crowd was transfixed. He returned the stare. Skitch Henderson, the bandleader, assumed Sinatra was joking around. Henderson remembered, “But then he captured my eye.” “I guess the color faded from my face as I observed his panic.” Finally, the singer stepped offstage, whispering “Good night,” and coughing up blood. He experienced a hemorrhage in his voice cords. Doctors advised Sinatra to refrain from speaking for at least a week. He had to cancel a trip to Chicago.

Sinatra’s career has already taken a turn for the worse. He was now in the woods, forced to compose musical nonsense until Capitol Records took a risk on him. The singer was connected with arranger Nelson Riddle by the company, and their cooperation rejuvenated Sinatra’s studio work. Sinatra redefined himself for grownups, embracing Riddle’s artistic, sophisticated orchestrations as an enthusiastic swinger on happy records or a broken-hearted brooder on pensive albums. Frank Sinatra was transformed into the cultural figure we know today thanks to his collaborations with Nelson Riddle.

The Riddle of Sinatra

In 1940, a slender young Frank Sinatra sings via a vintage microphone while bandleader Tommy Dorsey plays trombone. (Photo courtesy of Getty Images/Michael Ochs Archives) )

Inatra had been on top of the world for a long time. From a young age, the Hoboken, New Jersey native knew he wanted to be a singer. When trumpeter and bandleader Harry James dropped in one evening to assess the local talent, he was working as a singing waiter at the Rustic Cabin, a roadhouse in Englewood Cliffs, New Jersey. In February 1939, James employed Sinatra and paid him $75 per week.

Sinatra soon set his sights on the country’s best band, fronted by trombonist Tommy Dorsey. Sinatra left James in January 1940, deliberately terminating his singer’s contract, to negotiate a three-year deal with Dorsey for $125 per week. Sinatra gained a lot of knowledge by seeing the trombonist perform. In 1965, Sinatra told Life magazine, “He would take a musical phrase and play it all the way through seemingly without breathing for 8, 10, maybe 16 bars.” “Why can’t a vocalist do that as well?” Sinatra also listened to violinist Jascha Heifetz, who Sinatra admired for his ability to hold a melodic line without pausing. “I came up with the idea of making my voice work like a trombone or a violin—not sounding like them, but ‘playing’ the voice like those instruments.”

The Riddle of Sinatra

In 1943, Sinatra reunited with Harry James (far left) at the Hollywood Canteen for a single show for the troops. (Photo courtesy of Getty Images/CBS Photo Archive) )

As singers like Rudy Vallee, Russ Columbo, and especially Bing Crosby had done before him, Sinatra studied microphone technique and used amplification to bond with his listeners. Crosby biographer Gary Giddins observed, “He played the mic with a virtuosity that affected every singer to follow.” “It was his ultimate ally, well suited to his dynamic, nuance, and timbre way of working.” Because of amplification, singers didn’t have to belt to reach the balcony. They could finally whisper, sigh, and confess. Sinatra’s silky, calming baritone gave him the ability to sound as though he were singing directly to the listener. He came out as romantic, delicate, and vulnerable when singing ballads.

After being awarded America’s top vocalist by Billboard in 1941, Sinatra began negotiating to get out of his three-year contract with Dorsey, partly because Columbia Records CEO Emanuel “Manie” Sacks was offering a deal. Unlike James, Dorsey, on the other hand, was looking for a big payday. Both men were enraged by the negotiations. Dorsey told Sinatra, “I hope you fall on your ass.”

In 1944, trombonist Nelson Smock Riddle joined the Dorsey band. He was the only child of a domineering French mother and a sign-painter father, and he was born on June 21, 1921, in Oradell, New Jersey. The young man became interested in music and learnt to read music and play the trombone. He then began performing and arranging (developing the musical framework for songs) with local bands.

Bill Finnegan, Riddle’s first significant mentor, had been arranging for Glenn Miller since the late 1930s. Finnegan taught young Riddle how to experiment with different instrument combinations to create a unique sound for each tune he arranged in weekly classes. Classical music, according to Finnegan, is “the primary source of musical richness.”

Riddle freelanced as music arranger until bandleader Charlie Spivak hired him full time after Miller’s demands on Finnegan’s time forced him to quit teaching. “He was a great guy, extremely humble,” recalled Don Raffell, a saxophonist with Spivak. “He appeared to be intimidated all of the time. His mother was the root of the problem. She almost informed him when he needed to go the restroom.” Riddle was in the Merchant Marine during WWII, where he played in and arranged for the service’s orchestra until he moved to Dorsey’s band on May 11, 1944, in Chicago. “In his own gruff way, Tommy was cordial to me and fairly supportive of my burgeoning profession as an arranger,” Riddle remarked. “He was and always will be one of my heroes,” says the author. 

Riddle was influenced by Dorsey’s arrangers, listing Eddie Sauter, Hug Winterhatler, and Freddie Norman as examples.

Riddle was drafted into the Army in April 1945 and served for 14 months before returning to New York to freelance as an arranger until he was attracted to California by singer and radio show host Bob Crosby to handle that position for Crosby’s show. Riddle gained work writing music for NBC radio when that partnership ended. He also trained with Italian-born composer Mario Castelnuovo-Tedesco, whose symphonic arranging classes had a significant influence on him. In 1950, Riddle made his mark by arranging “Mona Lisa” for Nat King Cole. Riddle became a mainstay at Cole’s label, Capitol Records, because to that tremendous song.

While Riddle was learning the ropes, Sinatra was soaring to new heights. Young women known as “bobby-soxers” were enthralled by the tiny young man with the huge bow ties, the aching voice, and those blue eyes. In a 2010 biography, James Kaplan described Sinatra’s seven-year acting contract with Metro-Goldwyn-Mayer as “one of the sweetest deals in movie history.” At Columbia, Sinatra formed his first big musical connection with Axel Stordahl, an arranger/conductor and fellow Dorsey veteran. The pipe-smoking, professorial Stordahl encased Sinatra in almost classical arrangements, bald and tweedy. “A splash of strings and sumptuous, neo-Tchaikovskian arrangements to complement Sinatra’s lovely, lyrical, private, introspective ballad singing,” according to biographer John Rockwell. Sinatra’s collaboration with Stordahl earned him the moniker “The Voice.”

With the “Columbus Day Riots” on October 11, 1944, Sinatramania reached its pinnacle. The vocalist had been engaged at New York’s Paramount Theater, and his performance brought a throng of bobby-soxers, estimated to number in the thousands, to line up along Broadway and around the block. When the situation escalated, the 150-plus police officers on hand were no match for the teen hormones. The New Republic’s Bruce Bliven wrote, “Shop windows were smashed; individuals were injured and transported away in ambulances.” According to Kaplan, Sinatra’s performance at the Paramount was “a type of conclusion, the culminating explosive orgy of his religion of youth.” It appeared like World War II was drawing to a close, and that normalcy was on the horizon. Young fans of Sinatra were maturing.

Following the war, Sinatra became a star. He was squiring women not his wife, Nancy, around town when he wasn’t slugging reporters. His marriage was destroyed by an affair with the fiery actress Ava Gardner. His movie deal with MGM was canceled. His left-wing politics drew the attention of the FBI. Sinatra’s professional life was as tumultuous. His record sales were dwindling, his voice was strained, and the quality and appeal of his films were dwindling. The Copa problem was a physical symptom of a career on the decline. 

Mitch Miller, an oboist-turned-producer, was named chief of recording at Columbia. Miller was known for his gimmicky singles. Miller’s leadership of Sinatra signaled the nadir of the singer’s career, with the exception being Sing and Dance with Frank Sinatra, a 331/3 rpm 10-inch with up-tempo arrangements by George Siravo that went nowhere financially despite a high level of quality. “Mama Will Bark,” a duet with Swedish model Dagmar supplemented by a man howling like a dog, demonstrated Miller’s touch. In 1952, Sinatra and Columbia split ways.

The Riddle of Sinatra

Riddle was just another arranger in 1950, highly recognized but nonetheless part of the musical mainstream. (Photo courtesy of Getty Images/Bob Willoughby)

Frank Sinatra was a has-been at 37 when he desperately begged Columbia Pictures head Harry Cohn to cast him as the doomed GI Maggio in the adaptation of James Jones’ novel From Here to Eternity, set on the eve of World War II. Sinatra would receive an Academy Award for Best Supporting Actor for his performance. Then Capitol Records took a chance on him. 

Sinatra’s new label was credited to a number of people. Jo Stafford, a Capitol artist, said she recommended the singer to producer Dave Dexter Jr., who went to hear him and was compelled to give him a positive review. However, Capitol vice president for artists and repertoire Alan Livingston stated Sinatra’s representative had called him to measure Capitol’s interest. Livingston, a record business executive, told author Charles L. Granata, “Sinatra had touched bottom, and I mean bottom.” “He couldn’t obtain a record contract, and he couldn’t even get a nightclub booking at that point. It had gotten to the point where he was broke and in a nasty mood.”

Regardless, Livingston signed Sinatra.

Stordahl arranged and directed his debut Capitol recording, a 45-rpm single titled “Lean Baby” and “I’m Walking Behind You,” which was released on April 2, 1953. Sinatra desired to work with Stordahl, but the label encouraged him to work with Billy May, a loud, fun bandleader. However, because the hard-drinking trumpeter, who is noted for his band’s aggressive brass and “slurping saxes,” was on tour, Capitol turned to Riddle. “We were all crazy about Nelson; he was incredible!” According to Alan Livingston. “I wanted Frank to benefit from his knowledge of how to support a performer and make them sound great.”

On April 30, Livingston scheduled Riddle for a session with Sinatra. When Sinatra featured the Dorsey band on his radio show All-Time Hit Parade in 1944, the two men crossed paths, but Sinatra does not appear to have noticed the connection. 

The Riddle of Sinatra

The first compilation of singles and B-sides he recorded with Nelson Riddle was “This Is Sinatra” (1956). It includes the song “I’ve Got the World On a String,” which heralded the coming of a new Sinatra: rough, macho, and enthusiastic. (Alamy Stock Photo/PictureLux/The Hollywood Archive)

“When Frank walked in, he noticed a strange man on the podium and said, ‘Who is this?’” producer Alan Dell explained. “I told him, ‘He’s only conducting the band; we’ve got Billy May’s arrangements,” I said. Riddle had even made the session’s first two arrangements—”I Love You” and “South of the Border”—sound like May’s work, knowing Capitol’s inclinations; the label on the single “South of the Border” credits May. However, one chart was pure Riddle. With its brassy self-assurance, “I’ve Got the World on a String” heralded the birth of a new Frank Sinatra. The tremulous, fragile crooner of yesterday had transformed into a macho, happy, tough, enthusiastic figure. The tapes were listened to by Sinatra. 

He said, “Jesus Christ, I’m back.” “I’m back, darling, I’m back!” exclaims the narrator.

That session kicked off a three-decade relationship that resulted in 318 records, 25 television episodes, and the soundtracks to seven movie pictures, according to Riddle biographer Peter J. Levinson. 

Music historian Will Friedwald observed, “Sinatra and Riddle remained crucial to one other because each man pushed the other to heights neither could accomplish independently.” “And the Sinatra-Riddle sound has since become synonymous with Sinatra; the pre-Riddle era may be reduced to a prelude, and the post-Riddle era to an afterthought.”

Sinatra and Riddle appeared to be similar at first glance: both were Jersey lads and only sons of domineering moms. Both came out of the Big Band era and Tommy Dorsey’s service. But that was the end of the equivalency. The singer was a raucous boozer who flaunted his nerves on his sleeve. The arranger was quiet and introverted, with a caustic humor that stemmed from a bleak childhood. He was dubbed “Eeyore” by Julie Andrews. Riddle’s disposition was described by biographer Peter J. Levinson as “gloom and sadness.”

Riddle described recording with Sinatra as “tight and businesslike.” When the two met to explore approaches to the songs Sinatra wanted to sing, they began working on an album. Riddle remembered that he would begin by making “the most agonizingly exact comments on the first few tunes, often going to classical compositions for samples of what he anticipated to hear in the orchestration.” When he wasn’t recording, though, Sinatra was notorious for having a short attention span, and after providing a few specific instructions, he’d become hazy, eventually ordering Riddle to do what he thought was best. “My headache would begin to fade, my pulse would normalize, and another Sinatra-Riddle album would be released,” Riddle explained.

A third crucial component was mentioned by Riddle. “Music is sex to me,” he explained. “It’s all connected in some way, and the heartbeat is the rhythm of sex.” He considered his best stuff for Sinatra had “heartbeat tempo.”

The Riddle of Sinatra

“I’m back, darling, I’m back!” exclaims the narrator. Sinatra and Riddle pushed each other to new levels, resulting in some of the era’s most outstanding recordings. (Alamy Stock Photos/Records)

Riddle stated that the sessions were “charged with electricity.” In the studio, Sinatra was an outspoken activist. Despite not being able to read music, he was a fantastic musician who knew exactly what he wanted to record and was quick to notice and criticize problems. He may skip one arrangement and move on to the next, but he never does so in a rage. Riddle said, “He’d never give out compliments either.” “I’d know he was happy if he didn’t say anything. I never anticipated him to give me praise because he isn’t built to do so. He only wants the best from you.”

In a 1961 interview with Douglas-Home, Sinatra did offer a few praises. “Nelson is the world’s best arranger,” he stated. “He’s a brilliant musician, and I like him tremendously. Calm and little aloof, he’s like a tranquilizer. He is unaffected by anything. The music he makes has a great deal of depth to it.”

Songs for Swingin’ Lovers, Sinatra and Riddle’s second full-length album, may be the pinnacle of their collaboration. The album was recorded over the course of six days in January 1956 in Capitol Studio A at 5515 Melrose Avenue in Los Angeles, with the vocalist and musicians in the same room. Capitol mixer John Palladino told Charles L. Granata, “Frank always preferred to be on stage with the band.” “He wanted to make eye contact with everyone, and he charged the musicians—that was what made his sessions so unique.”

The album begins with “You Make Me Feel So Young,” a lighthearted start to Sinatra’s Capitol tenure. The first half concludes on a more contemplative note with George and Ira Gershwin’s “Love Is Here to Stay.” The song begins with Sinatra’s long-time pianist Bill Miller, one of a legion of musicians that recorded with the singer and Riddle throughout the years. Another was trumpeter Harry “Sweets” Edison, whose muted instrument always added the right amount of levity to any performance. Another was bass trombonist George Roberts, whose sound influenced Riddle’s work and eventually contributed the foreboding melody line in John Williams’ Jaws theme.

Milt Bernhart, a trombonist, shines on the outstanding track, Cole Porter’s “I’ve Got You Under My Skin.” On January 12, 1956, Sinatra added the chart at the last minute—to arrange it, Riddle pulled a late-nighter—and recorded it. The musicians gave him a standing ovation after he sang the song for the first time. From the opening baritone saxophones and bells through the bari saxes winding things down, “Skin” became an immediate favorite. Riddle complied with Sinatra’s request for a “long crescendo,” replicating Ravel’s “Bolero” in a middle part that raises the melodic temperature before Bernhart’s trombone solo brings the song to a fever pitch. Bernhart told Charles Granata, “I left the greatest material I played on the first five takes.” The brass section’s microphone was hung from the ceiling. The engineers requested more volume on take 10, according to Bernhart. Sinatra brought a box for Bernhart to stand on, bringing his horn’s bell closer to the microphone. After the instrumental break, Sinatra leans in for an emotional climax before bringing the song softly back to earth with the rest of the band. One of the indisputable gems of the Sinatra/Riddle repertoire is “I’ve Got You Under My Skin.”

Sinatra had numerous additional musical high points, many of which he shared with Riddle. There were peaks and dips, but Sinatra was never as close to failure as he had been before signing with Capitol. His contract with Capitol eventually became unsatisfactory. In 1960, he left the label for Reprise Records, which he created in order to avoid corporate domination. Riddle orchestrated five albums for Sinatra at Reprise after his Capitol contract expired. From the string-drenched symphonics of The Concert Sinatra (1963) to the jazz organ oozing through Strangers in the Night (1966), the Reprise tracks have exquisite Riddle arrangements—and they have Sinatra’s mature voice, aged like old bourbon.

Billy May, Don Costa, Quincy Jones, and Gordon Jenkins were among the arrangers hired by Sinatra in addition to Riddle. And Riddle kept busy, collaborating with Ella Fitzgerald, Judy Garland, Antonio Carlos Jobim, Oscar Peterson, and a slew of other performers, in addition to scoring films and television shows and producing albums with the Nelson Riddle Orchestra. 

The Riddle of Sinatra

Sinatra couldn’t read music, but Riddle guided him through the process of becoming a conductor. They worked together to find the song’s apex, after which Riddle would move out of the way. (Getty Images/Bob Willoughby)

Sinatra unexpectedly canceled an appearance at a tribute for Riddle in 1978, a snub the arranger could not forgive. Although Sinatra hired Riddle as musical director for a Ronald Reagan inaugural event in January 1985, the two never recorded together again. Nelson Riddle died on October 6, not long after arranging and conducting albums of standards for pop vocalist Linda Ronstadt that relied on his Sinatra sound.

When Frank Sinatra died in 1998, he was hailed as a giant of American popular music, a stature he owed to Nelson Riddle’s creative basis. According to Riddle biographer Levinson, “Nelson’s arrangements allowed Frank to swing like I’d never seen him swing before.” “That arrangement of ‘I’ve Got the World on a String’ sounded as fresh as anything we’d done before. I believe Nelson had a huge influence on the birth of the Frank Sinatra we all know and love.”

This article was originally published in the August 2023 issue of American History.

Richard “Sinatra” was the youngest child of a reasonably well-to-do family. He was born in Hoboken, New Jersey, in 1915. Richard Sinatra in his younger years.. Read more about nelson riddle iii and let us know what you think.

Frequently Asked Questions

Is Nelson Riddle still living?

Nelson Riddle is still living and well.

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Nelson Mandela

When did Nelson Riddle die?

Nelson Riddle died on October 23rd, 1982.

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