What accounts for a sustained, successful career? Talent might be the most important thing but there are other elements involved, including brains, timing, friends, the ability to evolve with the times, sex appeal, a bit of danger and risk, and sometimes just plain, dumb luck. Sinatra was smart enough, talented enough, and lucky enough to incorporate all of them into his remarkable career.
His rise came just as the country was going to war and our musical taste was slowly evolving from an infatuation with the instrumental sounds of the big bands (and their straight-ahead vocalists) to an interest in individual singers. Many of the best band singers were striking out on their own, taking center stage without the crutch (or the hindrance) of an orchestra. It was a brave act to step out but an artistically fulfilling one, as Sinatra himself proved. His whole career was guided by his innate desire to stretch as an artist, and he demanded a great deal from himself and all of those with whom he worked. He was unafraid to walk away from a gig or a contract, even during periods when his artistic or financial future was unsure; his self-confidence and drive rendered him unafraid of taking risks. This certainty would pay off spectacularly, until the very end of his career.
Sinatra’s big move came when he left Tommy Dorsey in 1942 (owing Dorsey thousands on his contract), and, from that point on, his career soared. He launched his solo career in a spectacular way, with a week of appearances with Benny Goodman’s orchestra at New York’s Paramount Theater on Times Square. We know now that some of the fans may have been paid to scream—but thousands of girls swooned for free during the weeklong engagement that anointed Sinatra the greatest popular singer of the day. His sense of humor, sex appeal, slight whiff of danger, and those mesmerizing blue eyes—not to mention the carefully chosen songs that resonated with his audience—made him an instant favorite of the bobby-soxers.
Sinatra’s decision to go it alone coincided with America’s entrance into World War II. Disqualified from service, Sinatra was still on the scene while much of the competition was occupied elsewhere, and the public’s interest in lyrics had never been stronger. “I’ll Be Seeing You,” a song Sinatra had recorded in 1940, took on new meaning for a female population unsure that they might ever see their boyfriends, brothers, sons, or husbands again. In 1944, the Sammy Fain and Irving Kahal song became a number one hit.
Sinatra had the good sense and taste to pick songs that suited him and that were perfect for the moment, and this carried him along brilliantly through the ’40s—but when that task was taken from him in the 1950s, when Mitch Miller was calling the shots for Columbia Records, Sinatra’s career plummeted to its lowest point. Ultimately, brains and technology saved the day. Sinatra broke his contract with Columbia and set out on his own, just when he was generally considered washed up both professionally and personally (His highly publicized marriage to Ava Gardner was kaput). He may have been down and out but he still had his intelligence and his high standards, and he spotted his next golden opportunity and took a leap that could be summed up by the quintessential Sinatra title, “All or Nothing at All.”
If his singing career was at a standstill, he reasoned, he should concentrate on his film career. The first half of Sinatra’s career started when he was signed by MGM after making his acting debut in RKO’s Step Lively in 1944. His early screen roles featured him as a sort of grown-up Bowery Boy, rough around the edges but eager to please. Anchors Aweigh (1945) found him paired with Gene Kelly and singing songs written by Jule Styne and Sammy Cahn, thereafter his favorite songwriters. It Happened in Brooklyn (1947) and Take Me Out to the Ball Game (1949) were among his MGM films. After 1948’s On the Town, Sinatra’s films became less and less successful both artistically and at the box office. He needed a change.
After reading James Jones’s bestseller From Here to Eternity, Sinatra lobbied hard for the part of Maggio and got it. The film came out in 1953 and soon he had an Oscar to join his Gold Records. Sinatra became a hot commodity in Hollywood and followed his stunning comeback with a remarkably diverse series of film roles. His 1955 output illustrates his high artistic goals as well as his refusal to be typecast: in that one year he took on lead roles in two dramas (The Man with the Golden Arm and Not As a Stranger), a musical (Guys and Dolls), and a comedy (The Tender Trap). But Sinatra knew his real claim to fame was his voice, and reviving his dormant recording career remained a priority. He signed with the newly formed Capitol Records and developed an entirely new singing style, a total departure from the formal, “square” techniques of the ’40s. He adopted a kind of loose, jazz-influenced style that was much more in tune with the ’50s. An army of arrangers kept him au courant, beginning with Axel Stordahl and continuing most notably with Nelson Riddle and Billy May. Many consider Sinatra’s Capitol period the greatest of his career.
Propitiously, the 33 1/3 rpm record was just coming into vogue, replacing the 78 rpm disc. On 78s, the choice of songs and their order hadn’t been so important, as individual songs could be easily purchased and played. As the 10-inch 78 was replaced by the LP, Sinatra and his producers were able to imbue these long playing records with concepts, carefully choosing the songs and their order. Once he was back on top, riding the popularity of such carefully crafted and enduring discs as In the Wee Small Hours and Songs for Swinging Lovers, Sinatra stayed there.
At the same time as his film and recording career were succeeding anew, Sinatra went to Las Vegas. His reputed mob ties came in handy, and Sinatra opened at the Desert Inn in September of 1951. His pioneering efforts in Vegas are credited with the city’s success. In the 1960s, Sinatra made Vegas the clubhouse for the Ratpack, an ultra-cool club of which he was the chairman. Members Sammy Davis, Jr., Joey Bishop, Peter Lawford, and Dean Martin followed their leader, and they held court onstage and in such films as Ocean’s Eleven (1960) and Sergeants Three (1962). Sinatra brought a sense of sophistication to the Strip, which had been a glorified cowboy town before his arrival, and during his reign, entertainment grew into an attraction on a par with gambling for many visitors.
Sinatra’s hip persona was a natural extension of his street smarts. His swagger, tilted hat, raincoat-over-the-shoulder style spawned a whole trend in attitude and became a blueprint for thousands of teenagers. Some of Sinatra’s acolytes like Sammy Davis, Jr., perhaps went too far in the ring-a-ding-ding lifestyle but Sinatra sailed through the years being true to himself.
Sinatra’s career faltered only at the very end, when his ego and boredom kept him performing and recording long past his prime. Still, audiences never stopped adoring him and even his horrific Duets albums (on which he teamed [in separate recording sessions] with contemporary pop stars many years his junior for indifferently recorded numbers), became bestsellers. It was a strange ending to a career marked by the highest artistic ideals—but nothing could erase the musical legacy of the man most consider the greatest singer of the twentieth century.
Sinatra’s nicknames included the Sultan of Swoon, the Voice, the Chairman of the Board, and Ol’ Blue Eyes.
Sinatra joined the Tommy Dorsey band and sang with the Pied Pipers. They had great success with the song, “I’ll Never Smile Again.” Jo Stafford explained to George Simon how much they loved working with him: “Most solo singers don’t fit too well into a group, but Frank never stopped working at it and, of course, as you know, he blended beautifully with us. He was meticulous about his phrasing and dynamics. He worked very hard so that his vibrato would match ours. And he was always conscientious about learning his parts.” Both Stafford and Sinatra admitted that they learned breath control from watching Dorsey play the trombone. (KB)
In this lyric Oscar Hammerstein emphasizes the sensory aspects of love. In the first verse he write about seeing a stranger, in the second about hearing her laughing, and in the third about feeling her call.Some Enchanted Evening
As Michael Feinstein tells it, Kander and Ebb had been hired to write the score for the musical film starring Robert DeNiro and Liza Minnelli. When they brought what they had created as the title song to the film’s director Martin Scorcese, Minnelli, and DeNiro and performed it for the first time, there was a long pause, after which DeNiro said “I don’t like it.” Kander and Ebb were stunned, but had no choice but to go back to their studio and make up something else. Channeling all their frustration, anger, and resentment into their work, they came back with a new title song to play for their finicky star. This time DeNiro said “I like it.” And that’s the song that was sung by Liza, later commandeered by Sinatra, and became a worldwide standard … and the bane of every piano bar pianist.New York, New York
In the summer of 1939, the Tommy Dorsey band flew to Toronto (the first time a band flew to an engagement) to play at the Canadian National Exhibition. Every evening a young girl named Ruth Lowe waited by the stage door in order to meet Tommy. This went on for most of the engagement. Band members noticed the girl and finally guitarist and arranger Carmen Mastren asked her what she was there for. She explained she had a demo of a new song that she considered perfect for the band. Mastren loved the demo and played it for Cliff Leeman who also loved the number—but for months no one could get Tommy to give it a hearing. Songwriter Ray Henderson listened to the demo and gave the song his approval. Once Henderson had listened to the song, Tommy relented, but wasn’t bowled over. In fact, he offered it to Glenn Miller, who recorded it at a relatively fast tempo. Finally, eight months after the Toronto engagement, Dorsey decided to record the song. Frank Sinatra and the Pied Pipers were looking for a way to perform it that would set it apart from the Miller version. They slowed it down and made it more intimate and conversational. They couldn’t get it quite right until Tommy suggested that they sing it as if they were just getting together informally at someone’s house. It worked—the song became one of their biggest hits.I'll Never Smile Again
It had a long range, very low and kind of very high, and it was long, as they all said, and I was trying to figure out what kind of dance could be arranged for it. I asked him to play it again and again, and after four or five times I began to get with it… It was a known fact that it made the show. Gay Divorce had an awfully rough trip when it first opened on the road and later in New York. It was known after it caught on as “The Night and Day Show.”Night and Day
Cole Porter was nonplussed when Astaire worried about singing the song because of the range. Porter replied, “Sure you can. I wrote it especially for your voice.”Night and Day
Ethel Waters knew she had a great song to sing the minute she heard this tune. “When I got out there in the middle of the Cotton Club floor … I was singing the story of my misery and confusion … the story of the wrongs and outrages done to me by people I had loved and trusted…. I sang ‘Stormy Weather’ from the depths of my private hell in which I was being crushed and suffocated.”Stormy Weather
One of the most famous songs to come from a Rodgers and Hart show wasn’t even written by them. Berlin’s “Blue Skies” was interpolated into the show Betsy and sung by Belle Baker. The opening-night reception was tumultuous, with Baker enjoying 24 encores—the last with composer Irving Berlin, who was summoned up from the audience. Talk about stopping the show!Blue Skies
When I write music I hear the orchestra, I don’t hear a piano. I play piano orchestrally, too. I hear the brass, I hear the woodwind. George Gershwin made a sound at the piano that he learned from a player piano he heard on the corner. He was playing the orchestra all the time. He felt more than he knew and that’s a wonderful thing. Feelings is the whole ball game. If you don’t have feelings you can’t compose you can’t sing. You can act feelings. I think that when Sinatra in the ’40s sang I think he was getting feelings that he hasn’t got. He was falling in love when he sang, he was talking to somebody. He just didn’t sing the words. He was inside the song. Sinatra always made the song his song. He took that song. Time After Time
Harold Arlen: "The words sustain your interest, make sense, contain memorable phrases and tell a story. Without the lyric, the song would be just another song."That Old Black Magic
Johnny Mercer meant his 1942 lyric, set to Harold Arlen’s tune, to refer specifically to Judy Garland, with whom he was having an affair. The song consists of the famous line: “I should stay away, but what can I do?”That Old Black Magic
The song “Laura,” so beautiful that both Cole Porter and Irving Berlin wished they’d written it, originally had a lyric by Irving Caesar. If David Raksin hadn’t adamantly rejected Caesar’s original lyric, Johnny Mercer’s life might have been radically different.
Johnny Mercer: If a fellow plays me a melody that sounds like something, well, I try and fit the words to the sound of the melody. It has a mood, and if I can capture that mood, that’s the way we go about it. Laura was that kind of picture. It was predesigned, because Laura was a mystery. So I had to write “Laura” with kind of a misterioso theme. That’s hard, because there are so few notes. And because the intervals are tough, the key changes are strange. And at the time it came out, it was most strange. But since it has become so popular, it’s easier now. That kind of song is always difficult because you have to write a lyric that’s going to be a hit, and you don’t have many notes to work with.Laura
Fox thought they had a bomb on their hands with the picture We Believe in Love, when producer Sol Siegel approached composer Jule Styne and lyricist Sammy Cahn to write a title tune for the film. Styne asked Siegel why the film wasn’t titled after the book on which it was based, Three Coins in the Fountain. Siegel asked if it would be easier to write for that title and Cahn replied, “It’s a helluva lot easier than ‘We Believe in Love.’” The team worked all night and the next day played the new song for Siegel and Zanuck. Spyro Skouras, then the studio chief, didn’t like it and commented, “the other title had ‘love’ in it and that’s a good thing.” It seemed that the song was dead, but Zanuck told Styne that if he could get a big name to sing it, he could get it into the movie.
Styne had written several hits for Frank Sinatra and he was determined to extract a return favor. Learning that Sinatra was returning to LA from Europe with a stopover in New York, Styne booked himself on the same flight and got a seat next to him. He implored Sinatra for help and, worn down, the singer agreed to record the song the very next morning—but he didn’t want to be paid. Rather, there was a certain painting in a gallery that he admired. Sinatra got his painting, and both the record and the film were smash hits. PS: the song won the Academy Award. As Jule Styne said, “The difference was Frank Sinatra. Without him, it wouldn’t have gotten off the ground.”Three Coins in the Fountain
Arlen considered this song one of his top two compositions.Last Night When We Were Young
"Love Is Here to Stay" was George Gershwin’s last song.Love Is Here to Stay
James Van Heusen explained to author David Ewen, “The song was written to dramatize Joe E. Lewis’s loss of his voice [in the film The Joker Is Wild] and the big jump musically at the end of the second bar to the middle of the third bar was specifically designed to be difficult for him to sing, and he was supposed to break down dramatically.”All the Way
Harold Arlen called this song one of his “tapeworms,” because the melody sort of wanders along. Arlen credited Mercer with much of the success of the song: “[It’s] a wandering song. Johnny took it and wrote it exactly the way it fell. Not only is it long—forty-eight bars—but it also changes key. Johnny made it work.”One for My Baby
Jule Styne: "I wrote the tune. I said [to Comden and Green], 'I’m just gonna write a top tune. Find a title to this, "da da da.”' You could call the tune anything. ‘da, da, da.” It sings by itself. For three months it was called ‘da da da.’ No title, they couldn’t write the song. So I said, ‘I’m gonna help you. I’m gonna see my friend Frank Loesser.’ This is done. Many lyric writers [have helped each other]—Leo Robin has helped Ira Gershwin—you need someone to talk to.
So, I went to Frank, I said, 'Frank, I’m writing with Comden and Green.' He said, ‘They don’t understand what a popular song is. What it consists of. It’s something that you remember melodically, not lyrically but melodically. You don’t remember the melody you ain’t remembering the song. They don’t understand that.’
So I played it for him. He said, 'It has to have a rolling title.' I played it over and over. I came back and he said, 'I have the title to the song, it goes, "Just in Time."' All he said was, 'Just in Time.' And they wrote a very good lyric to it. It’s a very good lyric. They’re very nice people. They’re very sophisticated people. They’re well learned and well read."Just in Time
“Cole Porter was my biggest fan. Told me, [‘Just in Time’] ‘is the most beautiful, attractive, pleasant, feel good song. You know when you walk into a room at a party there’s a band and they quickly play one of your songs when you walk in? I have a going order with the bands in California and New York when I walk in a room play "Just in Time." It makes me feel good.’”Just in Time
Arlen was noodling around on the piano looking for a tune when a phrase caught Johnny Mercer’s ear. Mercer exclaimed, “I’m gonna love you like nobody loved you…” Arlen jokingly replied, “Come hell or high water.” The proverbial light bulb went off over Mercer’s head and he answered, “Of course, why didn’t I think of that? ‘Come rain or come shine.’” The song was finished before the night was over.Come Rain or Come Shine
“I Won’t Dance” was written by Jerome Kern, Otto Harbach, and Oscar Hammerstein II for the 1934 London musical Three Sisters. The show was not a hit but Fred Astaire happened to see it and admired the song. When it came time to film Roberta at RKO, he suggested that the song be used in the film. Dorothy Fields amended the lyrics for the 1935 Hollywood version.I Won't Dance
“What’ll I Do” came to Berlin when he was slightly drunk on champagne and feeling sorry for himself at a birthday party. It seems Berlin wasn’t good enough for Clarence Mackay, the industrialist father of Ellin Mackay, Berlin’s intended. Eventually, Berlin got the girl and a hit song in the bargain.What'll I Do
Never has a romance resulted in more great standards than that of Irving Berlin and Ellin Mackay. His three greatest songs were written at the beginning of the affair, when Berlin was trying desperately to overcome the objections of Ellin’s powerful father. Mackay decided to send his daughter on a cruise, figuring that a long ocean voyage and crisp salt air would drive that skinny, Jewish songwriter right out of her heart.Remember
This 1940 song first became a hit in France under the title, “Perdu Dans un Reve Immense D’Amour.” Why in France? Because of the ASCAP broadcasting ban in the U.S. It wasn’t until 1950 that the song achieved widespread success in this country.Bewitched, Bothered and Bewildered
A preview of Breakfast at Tiffany’s in San Francisco didn’t go so well. At the meeting afterward, producer Marty Rakin said, “I don’t know what you guys are gonna do but I’ll tell you one thing, that damn song can go.”Moon River
In 1939 a contest was held by the publisher of Victor Herbert’s 1919 piano piece “Indian Summer,” requiring lyricists to add words to the tune. Al Dubin’s attempt came in first and the song became a hit recording by Tommy Dorsey with Frank Sinatra, and also by Glenn Miller and His Orchestra with a vocal by Ray Eberle.Indian Summer
This song was originally written in 1928 by Kurt Weill and Bertolt Brecht for their theatre piece, Die Greigroschenoper (The Threepenny Opera), which was based on John Gay’s The Beggar’s Opera. The song’s original title was “Morit’at,” an amalgam of the German words for “murder” and “deed.” Weill always said the song was inspired by the sound of Berlin’s traffic. When the show made its way to New York in 1933, it had lyrics by Gifford Cochran and Jerrold Krimsky, who called the song, “The Legend of Mackie Messer.” Nothing came of the song until 1954, when a revival of The Threepenny Opera opened off Broadway with lyrics by Marc Blitzstein. He titled the song, “Mack the Knife.” Blitzstein’s version was recorded by such diverse talents as Bobby Darin, Louis Armstrong, Ella Fitzgerald, and Rosemary Clooney.Mack the Knife
Shaw to Sam Litzinger of CBS Radio: "If I had to say something was perfect musically, the solo I did on ‘Stardust’ is as close to being perfect as I would have wanted."Stardust
In 1927, Hoagy Carmichael was sitting on the “spooning wall” of Indiana University pining for a girl named Dorothy. He ran to an old upright piano in The Book Nook and finished the song. A great story but apparently not true. Carmichael appears to have been working on the song since 1926. He even wrote a lyric to the tune which contained the words “Star Dust melody.” However and wherever it happened, Carmichael recorded it in 1927 for Gannett Records. Publisher Irving Mills took the song to Mitchell Parish and with its melody slowed down Parish wrote new lyrics for the tune. Carmichael’s friend (and lyricist for “Georgia on My Mind”), Stuart Gorrell, came up with the title, “Star Dust,” as the melody reminded him of “dust from stars drifting down through the summer sky.”
In 1936 RCA pressed what must certainly be one of the most unique records of all time—“Star Dust” on both the A and B sides of a 78 with Benny Goodman’s Orchestra on one side and Tommy Dorsey’s on the flip.Stardust
"I says, Frank, we have to split. I’m no good for you, Frank. Cause I’m writing for you. You have to sing other things. It’s not good for me. Every song I write is a Sinatra song. I gotta go write for some other people, I have another dimension for me. And that’s when he got angry at me. He thought I’m dismissing him. He didn’t understand it. I play him 'Just in Time,' I tell him I’m writing a Sinatra song. I didn’t want to tell him it was a Fred Astaire song. I met Fred Astaire at a party once. I said, 'Gee, it’s too bad I didn’t write some of the songs when you were dancing away. You know I’ve been writing Fred Astaire songs my whole life. Don’t tell Sinatra, he thinks they were his songs.'"Jule Styne
"It is Billie Holiday, whom I first heard in Fifty-second Street clubs in the early thirties, who was and still remains the single greatest musical influence on me."Frank Sinatra
"That's what I'm going to do."Frank Sinatra
"I’ll leave the music to somebody else. I pick the lyrics."Frank Sinatra
"The only good thing it did for me was with dogs."Frank Sinatra