"The kid's name is Sinatra... No one ever heard of him, he's never had a hit record, he looks like a wet rag, but he says he's the greatest. If he hears you compliment him, he'll demand a raise tonight."
—attributed to Harry James

Around January 1940 Frank Sinatra made his debut as the new boy-singer for Tommy Dorsey's band. At 24, Sinatra was hardly a boy. He'd already completed a grinding apprenticeship, first touring as part of the Hoboken Four and then singing at every opportunity he could scrounge up around his native New Jersey until he finally managed to land a regular gig at the Rustic Cabin. Though the job required him to be a singing waiter, the Rustic Cabin had a direct radio wire to WNEW which allowed Sinatra's voice to cross the river into New York City. After a brief stint with the Harry James Band, Sinatra (with James' blessing) jumped ship to join the more popular Tommy Dorsey Band. Not surprisingly, Sinatra's recordings during his years with Dorsey (collected on the 5CD RCA box set "The Song is You") show little development. Already full of confidence, Sinatra glides into songs with perfect timing, sustains notes for extraordinary lengths of time and effortlessly handles tricky phrasing. Still, Swing Era bands made dance music, and the real star of the Dorsey-Sinatra recordings is the big band itself. In a sense Sinatra was lucky; it had only recently become the fashion that bands required a regular vocalist. When Bing Crosby began singing with Paul Whiteman's band, he was required to sit holding a dummy instrument so as not to look odd to the audience.

During Sinatra's tenure with Dorsey, Sy Oliver and Axel Stordahl did many of the arrangements, Buddy Rich was frequently on drums, and occasionally Bunny Berigan would show up to play trumpet. The songs ranged from the dreck of the day ("I'll Take Tallulah") to the songs that Sinatra would record throughout his life ("Night and Day," "Everything Happens to Me"). Opening with Dorsey's trombone and leaving ample room for instrumental solos, most of these recordings clocked in at around 3 minutes. In fact, only one of the Dorsey-Sinatra sides—they made close to 90—is over 4 minutes long ("Without a Song"). Sinatra did not have the authority to dictate the tempo, which too often collapsed songs into band showpieces. For example, on "I'll Be Seeing You," which was recorded in 1940, The Tommy Dorsey Band runs through a clipped arrangement which forces Sinatra to sing in a peppy manner that is entirely inappropriate to the language of the song. The Dorsey-Sinatra recordings show what an extraordinary vocalist Sinatra had become, but working in a big band did not afford him many opportunities to develop his artistry as a singer. Eventually, Sinatra decided to go solo. Even though he gave Dorsey notice of his plan a full year in advance, it was still a shock. After all, at the time, the only truly successful pop singer who wasn't linked to a band was Crosby.

"Sure, I'm a Crosby fan. Everybody's a Crosby fan."
—Frank Sinatra

Dorsey told Sinatra that the one singer he should be listening to was Bing Crosby. Old news to Sinatra; as a kid he had a picture of Crosby taped above his bed. Bing Crosby has been reduced in our cultural memory to the "White Christmas" guy who once did a duet with David Bowie. This is unfortunate, because despite his public persona as a pipe-smoking, mild-mannered golfer, Crosby became the most significant singer in the first half of this century through a revolutionary approach to singing. Earlier singers like Al Jolson and Eddie Cantor had felt the need to project their voices in the style of theater. Crosby was the first to understand that the invention of the microphone allowed for a less showy and more focused style of singing. When Bing Crosby recorded his classic version of "I'll be Seeing You" (1944) he slowed the tempo and used lingering phrasing to make his interpretation work. (Always competitive, Sinatra, using an arrangement much closer to Crosby's, again recorded "I'll Be Seeing You," for his 1961 Capitol album Point of No Return.) Though his whistles and trills eventually assumed their own mannered style, Crosby's "crooning" helped bring about the era of pop vocalists, uniting theater tunes with the ease of jazz phrasing. In large part, Sinatra's entire career involved capitalizing—in ways Der Bingle never could—on the possibilities inherent in Crosby's approach.

After a slow start, Sinatra the solo artist was a sensation. In the middle of 1943, the bobby soxers made Sinatra famous by swooning and throwing their underwear on stage at his performances. By 1944, Sinatra's shows at the Paramount Theater in New York City sold out the 3,600 seats inside, and left 30,000 fans outside wanting to get in. As would later be the case with Elvis Presley and then the Beatles, riots, hysteria and fandom drove a wedge between parents and their teenagers. Sinatra's recordings from the period, however, were not, as his many critics contended, schlock for teenagers, but neither did they exhibit the interpretive genius that marked his Capitol recordings.

Between 1943-1952 Sinatra recorded for Columbia Records (a good introduction is the 4CD Columbia/Legacy box set Frank Sinatra: The Best of the Columbia Years). These recordings while frequently meritorious and memorable are among the most conservative works in Sinatra's oeuvre. For many of his Columbia recordings Sinatra used fellow Dorsey veteran Axel Stordahl as an arranger. Stordahl specialized in ballad orchestrations which cushioned Sinatra's voice with heavy strings. In this context, Sinatra sounded far more like Crosby than he had before with Dorsey. Many of the musicians used on the Columbia sessions had worked with Crosby. Stordahl himself would record a number of sides with Crosby. Matters weren't helped by Sinatra's selection of material: many, if not most, of the songs Sinatra/Stordahl recorded were previously hits for Crosby; at Sinatra's first Columbia session with Stordahl (a musician's union strike had resulted in some earlier a cappella recordings) they recorded "White Christmas." Despite well publicized voice problems, Sinatra sounds superb throughout the Columbia years. If as an artist Sinatra had yet to fully emerge, these recordings capture some of his finest singing. For example, on "Ol' Man River," he delivers a superb reading that contains just enough fatalism to be neither as bombastic nor as patronizing as his later recordings of it. Other tracks like "Saturday Night (Is the Loneliest Night in the Week)," "Guess I'll Hang My Tears Out to Dry" and "She's Funny That Way" are pop music perfection.

Sinatra's most famous recording from his time on Columbia is "I'm a Fool to Want You." The lyrics, to which Sinatra contributed, reflected his adulterous and tempestuous relationship with Ava Gardner (whom he would later marry and divorce). Legend claims he sang it once and then left the studio, emotionally exhausted. In fact, Sinatra's version of "I'm a Fool to Want You," while certainly among the highlights of his Columbia years, does not sound near as tortured as Billie Holiday's reading of the song on Lady in Satin. Holiday's voice is a magnificent wreck of its former glory. Sinatra sings beautifully, but though the lyric should demand isolation, the Ray Charles Singers bolster Sinatra throughout the track with the aid of a busy violin. Sinatra is too good on "I'm a Fool to Want You," to declare the track overrated, but it is fair to say that he still had room to grow.

"Frank Sinatra is the kind of singer who comes along once in a lifetime—but why did it have to be my lifetime?"
—Bing Crosby

Sinatra's comeback as a celebrity with his Oscar winning performance in From Here to Eternity was remarkable enough, but his return to prominence as a singer was unprecedented. After he was dropped by Columbia, Sinatra was washed up. Though he had three number one hits in the 40s ("Oh, What It Seemed to Be," "Five Minutes More" and "Mam'selle), they were all eminently forgettable. As Sinatra approached 40, he was a second rate Bing Crosby, and he was now too old to be screamed at by teenage girls. Record companies didn't want him. Sinatra lacked not only a recording contract, but even a booking agent for live appearances. Finally, Sinatra was forced to sign with a ten-year-old label, Capitol Records, which had been having some hits with Les Paul and Mary Ford. Capitol Records, which at the time was not even technically a major label, only offered Sinatra a one-year contract the terms of which were almost an insult: Sinatra not only wouldn't receive any advance, but he was required to pay his own recording costs. Despite this inauspicious beginning, the relationship between Capitol and Sinatra lasted eight years; it helped Capitol become one of the world's most successful labels and it made Sinatra a living legend. When Sinatra left to form his own label, he pointed at the Capitol Tower: "I helped build that," he said, "Now let's build one of my own."

In part by design, but mainly because of changes in technology and in the marketplace Sinatra's recordings for Capitol fall neatly into two categories: singles (movie songs, novelty songs, experiments and new songs) and albums (carefully chosen, sequenced and arranged American standards by the likes of Porter, Kern, Gershwin and Rodgers & Hart). The singles (collected on the 4CD Capitol box set Frank Sinatra: The Complete Capitol Singles Collection) were the less ambitious recordings, but it was on a single that the "new" Sinatra first emerged.

Recorded on April 30, 1953, "I've Got the World on a String" is Sinatra's first pairing with arranger Nelson Riddle. Sinatra had wanted to keep working with Axel Stordahl, but was persuaded to try working with Riddle. Their collaboration would be among the most successful in popular music. Riddle kept his orchestra out of Sinatra's way and learned how to use bass, reeds and horns to underline and punch-up Sinatra's phrasing. Sinatra, too, had changed from his Columbia years. His voice became deeper and even richer, and his phrasing cleaved more closely to the emotional demands of the song. Less interested in showing off, Sinatra developed an assured confidence that allowed him to alter stress and even change the composer's words if it helped wed the music to the lyric. All of this is apparent on "I've Got the World on a String." Riddle opens with an orchestral volley which quickly vanishes, leaving Sinatra to sing the opening lines with only slight accompaniment: "I've got the world on a string/ Sitting on a rainbow/ got the string wrapped around my finger..." Then comes an orchestral explosion followed by Sinatra: "What a world/ What a life/ I'm in Love." Riddle uses a drum in a way that seems to anticipate Rock & Roll's back-beat. It is a wondrous recording.

Still, the cornerstone of Sinatra's achievement with Nelson Riddle is on the albums. Among the best: Songs for Young Lovers, Swing Easy, In the Wee Small Hours, Songs for Swingin' Lovers, Only the Lonely. The making of albums was still fairly new and many approaches were being tried: Crosby gathered together a variety of possible hits, Ella Fitzgerald recorded the entire songbooks of great writers. Sinatra's records from the period are frequently called concept albums, because the song selection tended to create a single mood. Some, like Only the Lonely even opened with a specially composed (usually by Sinatra regulars Sammy Cahn and Jimmy Van Heusen) title song which dictated the album's theme. Most of the songs on these records had been recorded by Sinatra before and many would be again. However, it is on these records that songs which had been standards, open to any interpretation, wound up unalterably Sinatra songs. On Songs for Swingin' Lovers alone, Sinatra puts a definitive stamp on "You Make Me Feel So Young," "You're Getting to be a Habit with Me," "Pennies From Heaven," "I've Got You Under My Skin" and "Anything Goes." Sinatra's readings are so persuasive that any later singer who attempted these songs had to either consciously sing around Sinatra (as Jimmy Witherspoon does on his 1965 recording of "Blues in the Night" which Sinatra sang seven years earlier on Only the Lonely) or give up and call their version a tribute. Those singers who came before, like Bing Crosby, found their interpretations erased from memory. Of course, this success created a problem for Sinatra as well: what to do for an encore?

"The taste of his martini didn't please his bitter tongue/ Blame it on The Rolling Stones."
—Kris Kristofferson

Sinatra made no secret of his hatred for Rock & Roll; he published a piece describing the music as: "brutal, ugly, degenerate, vicious." Over the years, he went out of his way to pick feuds with rock stars as diverse as George Michael and Sinead O'Connor. While rock music may have supplanted Sinatra's style of music, it had no discernable impact on Sinatra. Though Buddy Holly and Elvis Presley arrived during his tenure at Capitol, Sinatra produced nineteen Top Ten albums for that label. It may seem surprising, but even throughout the 60s only the Beatles sold more albums than Frank Sinatra. In 1961 Sinatra started his own label, and within three years he recorded his first ten albums for Reprise Records.

Though prolific, inspiration was clearly lacking on many of Sinatra's Reprise recordings. Frequently, Sinatra seemed to be singing by rote. His voice stiffened and his phrasing became more edgy and forced. Also, Sinatra, applied his finger-snapping "Ring-a Ding Ding" Vegas style to songs indiscriminately. Though hardly in need of money, in many cases Sinatra seemed to be revisiting earlier triumphs for reasons that had far more to do with commerce than aesthetics. By re-doing many of his trademark songs, Sinatra was able to release Reprise "Greatest Hits" albums to compete against his back catalogue which, to his chagrin, was continuously being marketed and re-packaged by his former labels. On the 1997 collection The Very Best of Frank Sinatra (2CD Reprise) nearly half the selections are 60s versions of songs Sinatra had done in the 40s and 50s. Perhaps the most egregious: a 1963 version of "In the Wee Small Hours of the Morning." In 1955 Sinatra had recorded a heart-stopping version of this song with Nelson Riddle as the title track for one of his greatest concept albums. Whereas in earlier periods Sinatra had returned to familiar songs only to find new meaning in them, the 1963 "In the Wee Small Hours of the Morning" retains a Riddle arrangement, and Sinatra uses similar phrasing; it is isn't different, only inferior.

Still, if Sinatra was no longer making music for connoisseurs, the Reprise years produced many of his most popular performances. "That's Life," "New York, New York" and "My Way," all cast Sinatra as a bloodied but unbowed fighter kicking the ass of old age. In a famous 1965 essay, "Frank Sinatra has a Cold," Gay Talese wrote, "[H]e makes old men feel young, makes them think that if Frank Sinatra can do it, it can be done." But a less generous listener might detect on these tracks the bluster of an aging hipster railing against the obvious: his own irrelevance.

Of course, this isn't to say that Sinatra's recordings for Reprise lacked merit, or aren't worth hearing. The voice is still Sinatra's and he is accompanied by first-rate bands including those of Duke Ellington, Count Basie and Antonio Carlos Jobim. Nor did his work for Reprise lack ambition. Though the results were often a disaster (like A Man Alone his 1969 setting of Rod McKuen lyrics), until the end Sinatra was an artist willing to take risks; sometimes, as on September of My Years, the risks paid off. Released in 1965, September of My Years is rightly regarded as Sinatra's final masterpiece. The opening Van Heusen/Cahn title song recalls the Capitol concept albums. This time the theme is age, decay and encroaching death. Gordon Jenkins' string-filled arrangements remind the listener of Axel Stordahl's settings for Sinatra at Columbia. But instead of soaring, Sinatra allows his weathered voice to push against the lush arrangements—he explores every crack and break that the years have given him. While many artists have made recordings about premature death, or talent struck down in the prime of life, popular music, especially during the rock era, has avoided the subject of aging like a taboo. September of My Years remains one of the few recordings in popular music to face natural mortality.

Except for a brief retirement in the early 70s Sinatra never quit. He continued to tour until the end of 1994 when he was 79 years old. Also, in the 90s he recorded two albums of duets with absentee partners who were dubbed in later. They were awful but still topped the charts. The lack of thought that ruined these records is made clear by a duet (tacked on to an album inexplicably titled Sinatra 80th: Live In Concert) with opera singer Luciano Pavarotti on "My Way." Pavarotti has no feel for the phrasing or meaning of the song. There is no interaction between Pavarotti and Sinatra; they simply take turns singing. But worst of all is the basic choice of material: "My Way," a song proclaiming self-determination, is simply wrong as a duet.

In 1994 Bono from U2 presented Sinatra with a Legend Award for Lifetime Achievement at the Grammy Awards. "Rock & Roll people love Frank Sinatra," Bono said, "because Frank Sinatra has got what we want: swagger and attitude. He's big on attitude, serious attitude. Bad attitude." But this caricature has nothing to do with Sinatra's real achievement: a remarkable range of recordings spanning over half a century. "May you all live to be four hundred years old," Sinatra would say when toasting his audience, "and may the last voice you hear be mine."