n the 1940s Frank Sinatra was “The Voice.” By the 1950s he had become the “Chairman of the Board,” and from the 1970s until his death in 1998, “Ol’ Blue Eyes.” He first gained fame as the boy singer in Harry James’s and Tommy Dorsey’s big bands. His fame grew through concert and radio performances; followed by record albums, movies, and television; and now CDs, DVDs, Ipods, satellite radio, YouTube, and every other form of digital media. Over the decades his audience has varied enormously. It began, and much later concluded, with a surprising number of young people and hip musicians.

Most of Sinatra’s entertainment career—from the mid-‘40s to the mid-‘80s—was also spent on the political stage. By the time he switched from Democrat to Republican in the 1970s, celebrities’ active support for candidates and causes had become commonplace. But when Sinatra endorsed and campaigned for Franklin D. Roosevelt in 1944 and, the following year, championed racial and religious tolerance in a film short called The House I Live In, he was out on a limb. At the time, the better part of valor was for entertainers to avoid political controversy, on the assumption that taking a stand—any stand—would alienate millions of ticket- and record-buyers.

Last Saturday, December 12, 2015, marked the centenary of Sinatra’s birth. He is, the poet David Lehman notes, a figure about whom “hundreds of thousands of words have been written.” That’s too low: show-business author James Kaplan has cleared that bar all by himself. His new half-million-word Sinatra: The Chairman follows his 400,000-word first volume, Frank: The Voice, published in 2010 (reviewed in the Summer 2011 CRB).

And Kaplan has no monopoly. There are new or updated books by Spencer Leigh, J. Randy Taraborelli, and Pete Hamill, plus two coffee table books: Charles Pignone’s Sinatra 100; and Andrew Howick’s Sinatra: The Photographs. I’ve lost count of what was published just last year. Lehman’s Sinatra’s Century: One Hundred Notes on the Man and His World comprises exactly that number of short essays (some just a few lines) in honor of each of Sinatra’s 100 years, living and dead. These books tell us more about Sinatra’s marriages, extramarital affairs, run-ins with the press, and mob connections than we need to know, but also much that’s valuable about his music, politics, and place in popular culture.

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The music must come first. When Sinatra hit it big in the 1940s, his main appeal was to the teenage daughters of white working-class families—the so-called “bobby-soxers.” The New Republic and the New Yorker sent correspondents to try to figure out what caused 30,000 girls to line up for one of Sinatra’s six daily shows at New York’s Paramount Theatre on October 12, 1944, and then riot when nearly 90% of them found out they weren’t going to get in.

Various theories, most involving sex, purported to explain “Sinatramania,” “Sinatrance,” or even “Sinatrauma.” In truth, girls mainly liked Sinatra because when he sang he seemed so much like them. The few who found seats in the Paramount may not have been able to hear him over each other’s screams, but from listening to the radio they already knew all the songs. “Time has vindicated the taste of the bobby-soxers.” Lehman writes. Sinatra built his reputation, at a time when popular music was all about new and danceable numbers, by getting audiences to sit down to a repertory of old songs from forgotten Broadway musicals by composers such as George and Ira Gershwin, Irving Berlin, Jerome Kern, and Cole Porter. “When the dancers stopped dancing and gathered around the singer to listen, the change was monumental,” Lehman adds. “The singing became the main event.”

Sinatra’s early performances underscored his 1940s persona: sweet, shy, slight, light-voiced, even androgynous. Of the seven Sinatra-inspired characters that appeared in animated cartoons of the period, four were cute animals. (Three of these cartoons are bonus features in the new Frank Sinatra 5-Film Collection, one of several compilations on DVD). In early movies, Sinatra usually played “physically and emotionally vulnerable characters.” Literary scholar Rob Jacklosky points out that in The Kissing Bandit Sinatra is the “bandit who won’t kiss,” and in Anchors Aweigh he’s “the sailor who can’t score.” Jazz critic Francis Davis, writing shortly after Sinatra’s death, observed, “Often what young girls want in a boy is another girl, and the girls who swooned over Sinatra pressed him to their hearts as a young man who was as sensitive and, on some level, as self-conscious as they were.” Think of the early Leonardo DiCaprio, before he buffed up.

From the beginning, a remarkable number of Sinatra’s hits were originally written for and sung by women, including the Gershwins’ “Someone to Watch over Me,” “My Funny Valentine,” by Richard Rodgers and Lorenz Hart, and “I Got It Bad (And That Ain’t Good),” by Duke Ellington. Such “ballads of longing or lament were assigned to female characters,” writes Philip Furia, “on the conventional assumption that women were more given to wistful or melancholy effusions.” The era’s male singers not named Sinatra didn’t dare to show such vulnerability.

Sinatra chose to reinvent rather than simply revive old songs. “Listen to the original recordings of the great Rodgers and Hart numbers,” Adam Gopnik recently wrote in the New Yorker, “and you will be amazed—and a little shocked—by how much of the thrum and vibrato and rhythmic squareness they retain. They become the songs we know when Sinatra begins to sing them.” Songwriters loved what Sinatra did for their forgotten compositions—but often resented the revisions. “Cole Porter didn’t appreciate ‘you give me a boot’ in ‘I Get a Kick out of You,’” notes Lehman. “Ira Gershwin did not get a boot out of the insertion of ‘much’ to modify ‘alarm’ in ‘A Foggy Day.’”

Sometimes Sinatra made these changes to punch up the rhythm, sometimes because the bel canto vocal style he favored required variety of expression when repeating the chorus. “It can’t be ‘one-two-three-four/one-two-three-four’ because it becomes stodgy,” said Sinatra. “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.’” Soon after he put them on disc, the songs Sinatra performed became “Sinatra music” even though he wrote very few of them. With his voice, not his pen, Sinatra revived the music that later became the Great American Songbook, and established himself as its leading interpreter.

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Sinatra’s early appeal wasn’t confined to teenage girls. Musicians admired his extended, almost conversational phrasing, the product of harnessing extraordinary breath control to deep lyrical intelligence, and his in-the-pocket sense of rhythm. When Sinatra sang a song, it seemed as if he were thinking it up as he went along—and feeling what he was thinking. “In front, dead center, and slightly behind” the beat, Sinatra’s phrasing of a song made his interpretation sound “as though it were inevitable,” said Quincy Jones. “That’s the mystery,” writes Gopnik: “he’s perfectly faithful to the songs and wonderfully free with them.” In 1941, at age 25, Sinatra bumped Bing Crosby out of first place as the jazz magazine Down Beat’s best male singer. In a 1956 survey of 120 jazz musicians, 56 rated Sinatra first in that category. His supporters included Ellington, Miles Davis, Benny Goodman, Gerry Mulligan, and Lester Young.

Sinatra’s decline after World War II and subsequent comeback is an oft-told tale, nowhere better than in Kaplan’s two volumes. He fell out of musical fashion and into romantic turmoil, but then won the 1954 Academy Award for From Here to Eternity and made a series of stunningly successful Capitol records with arrangers Nelson Riddle, Billy May, and Gordon Jenkins. An amended persona helped broaden Sinatra’s audience: fewer girls, more women…but also men. The Sinatra who climbed out of the hole was tough—a raffish swinger, not the sensitive girlie-man of the ‘40s. But the masculinity also conveyed doubts and insecurities, to which Eisenhower-era males, adjusting to new lives as organization men with mortgaged suburban houses, responded. Sinatra bared his vulnerabilities when he sang and men, reluctant to appear weak, appreciated his doing it for them.

Literature professor Roger Gilbert has argued that in nearly all his music, “Sinatra enormously expanded the emotional palette of his art, incorporating shades of self-pity, longing, rage, bitterness, panic, and despair that no popular singer had previously touched.” He continued to mine the musical past for excellent material—the songs on his albums often averaged 20 years of age—while commissioning new songs from in-house composers Sammy Cahn and Jimmy Van Heusen and mining more recent Broadway shows by Rodgers and Oscar Hammerstein, Alan Jay Lerner and Frederick Loewe, and Frank Loesser.

More than that, he organized these songs into a series of “concept albums,” a Sinatra innovation in which cuts were arranged like chapters in books: about heartbreak (Frank Sinatra Sings for Only the Lonely); rueful acceptance of loss (In the Wee Small Hours of the Morning); or romantic exhilaration (Songs for Swingin’ Lovers). Meeting with the arranger he had chosen for an album, Sinatra would share his thoughts about instrumentation and tempo. On Only the Lonely, for example, Riddle’s chart for “Angel Eyes” has the large, strong, and wind-dominated orchestra fall steadily out of meter, suggesting the singer’s descent into aimless despair. “Ebb Tide,” on the other hand, grows into meter, as the singer, initially tossed about on roiling ocean waves, attains a certain peace.

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The rock-dominated 1960s were difficult for Sinatra musically but also creative, more so than Kaplan and Lehman recognize. Though disdaining the new music, he still wanted to sell records. Some of the contemporary songs he recorded for the singles market were both popular and excellent, like “Summer Wind” and “It Was a Very Good Year,” the latter a “tapeworm” in music business lingo because it was much longer than the standard 32 bars. Others were merely popular. Sinatra was thrilled that “Strangers in the Night” reached the top of the charts, his first song to do so since 1946, and knocked the Beatles out of first place. But he once introduced the song at a concert in Jerusalem by saying, “I just cannot stand this song…but what the hell.” He even disliked “My Way” because, “I hate immodesty, and that’s how I feel every time I sing the song.” Though brash in other settings, Sinatra was self-effacing when he sang, nearly always saluting the composers, arrangers, and musicians when introducing a song at his performances, rarely recording a boastful lyric.

The desire to stay fresh, which motivated Sinatra’s continuing quest for hit records, also led him to keep innovating artistically. Most notably, he embraced the new blend of samba and jazz that was Brazilian bossa nova, recording 20 songs with Antonio Carlos Jobim, the young composer of nearly all the genre’s trademark numbers, including “The Girl from Ipanema” and “Quiet Nights of Quiet Stars.” Sinatra’s singing on these recordings is unlike anything he had ever done, so soft and delicate as to seem feathery. In his quest for new sounds, Sinatra also made jazz-inflected albums with Ellington, Count Basie, and new arrangers: Quincy Jones, Neal Hefti, and Johnny Mandel among them.

Sinatra’s recording career slowed in the 1970s in favor of concert performances in massive arenas. His 1980 concert at a Sao Paolo soccer stadium drew 175,000, the record for a live audience. Records were forever, Sinatra knew, and he was right. All of his albums are still available for downloading and on CD, and someone wanting an introductory course in Sinatra’s music could do worse than Ultimate Sinatra, a recently released 4-CD anthology of his recording career that begins with “All or Nothing at All” in 1939 and ends with “Theme from New York, New York” in 1979. A 4-CD collection of live radio broadcasts from 1935 to 1955, Frank Sinatra: A Voice on the Air, is nearly as good and barely overlaps his studio recordings. It’s your one chance to hear him sing “Tenderly” and “Long Ago and Far Away,” not to mention “Take Me Out to the Ball Game.”

Sinatra’s screen acting, meanwhile, seldom as strong as his singing, came to a virtual stop. (He appeared in at least one movie each year for the 15 years after From Here to Eternity, but made just three films after 1968.) Sinatra thought that movies were ephemeral, an opinion formed in his youth when new motion pictures would disappear after a few weeks at the Odeon. In this he turned out to be wrong. Television, tapes, discs, and on-line streaming have made movies as eternal as records. In the recording studio Sinatra lavished care on each song, doing take after take in the belief that “what we’re putting on that tape might be around for a lotta, lotta years. Maybe long after we’re gone somebody will put a record on and say, ‘Jeez, he could have done better than that.’” But on movie sets, he was “one-take Sinatra,” always impatient.

The benefit of Sinatra’s hasty film-making was spontaneity, some of which invariably would be lost after a scene’s first run-through. Kaplan shows that this approach could work, if a strong director rehearsed the other actors before Sinatra did his take. Otto Preminger got an Oscar-nominated performance out of him in The Man with the Golden Arm and John Frankenheimer elicited Sinatra’s best performance ever in The Manchurian Candidate. All too often, though, Sinatra chose lousy material, ran roughshod over directors, and made movies that ranged from the execrable Dirty Dingus McGee to mediocrities that could have been excellent, like the musical Robin and the 7 Hoods.

But if acting is at its core the portrayal of character in circumstance, then nearly every time Sinatra sang he became one of the greatest actors of all. Kaplan recounts the story of Raquel Welch dragging legendary director Elia Kazan to a Sinatra concert. Kazan had made clear going in that he hated Sinatra for disdaining movie directors. But “halfway through the first song,” Welch said, Kazan called Sinatra “the best actor I’ve ever seen in my life. He’s completely naked up there.”

Movies and, especially, music made Sinatra the leading entertainment figure in the country from the mid-‘50s to at least the mid-’60s. But he never lost the sense of being a little guy that he developed growing up in Hoboken, the son of a small-time boxer and bar owner. Sinatra campaigned widely for FDR in 1944, telling a national radio audience on election eve, “Since he is good for me and my family, he must be good for all the other ordinary guys and their kids.” He named his son after FDR: Born in January 1944, Frank Sinatra, Jr., has the first name Franklin, not Francis. Left-wingers were drawn to Sinatra’s other ardent public passion, civil rights, a cause very few mainstream entertainers championed. Nearly all the people involved in making The House I Live In were committed leftists. The song of the same title that Sinatra sang, which declares that America is not “a name, a map, a flag I see” but rather “the worker by my side” and “all races and religions,” was virtually a hymn to the Popular Front.

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Sinatra’s political involvement attracted the FBI’s attention. Historian Jon Weiner, in a 1986 article titled “When Old Blue Eyes Was ‘Red,’” uncovered this jarring entry in the New York Times Index for 1949: “Sinatra, Frank: See US—Espionage.” But Sinatra remained active in politics. Craving respect commensurate with his wealth and fame, he did everything in his power—from singing at fundraisers to persuading mafia boss Sam Giancana to rally Teamsters’ support in the crucial West Virginia primary—to help elect John F. Kennedy in 1960. In 1968 Sinatra worked almost as hard for Democratic presidential nominee Hubert H. Humphrey.

To be Italian-American through most of the 20th century meant being tainted by the country’s facile assumptions about ethnic inferiority and organized crime. To be a singer in nightclubs meant doing business with unsavory characters. (So, for that matter, did growing up in many Italian neighborhoods.) “To Sinatra, and to many Italians,” wrote sociologist Daniel Bell in 1953, mobsters “were bywords in the community for their helpfulness and their charities.” Sinatra did not run away from his heritage or his associates. Most Italian-American performers, including Anthony Di Benedetto (Tony Bennett) and Dino Crocetti (Dean Martin), believed changing their names was a necessary career move. When Harry James suggested that a name like “Frankie Satin” or “Frankie Trent” might broaden the appeal of his band’s young singer, Sinatra replied, “No way, baby. The name is Sinatra. Frank f—ing Sinatra.”

Sinatra’s hope was that political involvement at the presidential level would cause people to associate him with statesmen rather than mobsters. The opposite occurred. President Kennedy and presidential nominee Humphrey both heeded warnings from their advisers to distance themselves from Sinatra. In each case the news media explained Sinatra’s exile by recycling every ugly incident, association, and allegation—real and imagined—in their Sinatra clips files.

Abandoned by his party, Sinatra switched to the GOP in the early 1970s. Unlike Democrats Sinatra had supported, Richard Nixon and Ronald Reagan seemed to understand loyalty the same way he did. Nixon invited Sinatra to sing at a state dinner for the Italian prime minister. Reagan wrote a letter that helped him get a casino license in Nevada and then asked him to organize his 1985 inaugural gala. More than that, Lehman argues, “What happened to Sinatra’s politics was not all that different from what a neoconservative like Irving Kristol went through: the conviction that the liberal ideals of their youth were not being served by the Democratic Party” as it swung toward the cultural left.

Sinatra’s political shift reduced his appeal to the rapidly growing ranks of young people on college campuses, many of whom followed the Democrats leftward. Indeed, everything about Sinatra seemed wildly out of step with the new campus culture: Vegas instead of Woodstock; booze instead of grass; tuxedos instead of jeans; “broads” and “chicks” instead of “women” (much less “womyn”); strings, woodwinds, and brass instead of electric guitars. Above all, Sinatra music was “parents’ music” at a time when everything about their parents irritated college-age children. And when Sinatra did try to appeal to the young—recording a swing version of Simon and Garfunkel’s “Mrs. Robinson” or appearing in a Nehru jacket on a television special called Frank Sinatra Does His Own Thing—he seemed as clueless as any dad with sideburns and a leisure suit.

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Sinatra retired in 1971, at age 55, and when he came back two years later to go on the concert circuit his target audience was people old enough to have loved him in the ‘40s and ‘50s. But over time a strange thing happened. Young people began showing up at the concerts, buying his records and working back from the filmed remakes of Oceans 11 and Manchurian Candidate to the original Sinatra versions. Many even began liking Ronald Reagan.

Joe Piscopo and Phil Hartmann made Sinatra impersonations a regular Saturday Night Live feature, and in 1991 David Letterman offered a not-bad-for-a-75-year-old-man list of “Top 10 Signs Your Wife is Seeing Frank Sinatra” (No. 1: She comes home smelling like a sweaty tuxedo.) Gilbert Gigliotti found that of the 50 songs written from 1945 to 2001 that mentioned Sinatra, 25 appeared after 1991, including numbers by Bon Jovi, Smash Mouth, and DJ Eddie Def. Bonz Malone identified Sinatra in the rap-hip hop magazine Vibe as the original gangsta.

How to explain the late appearance of young people in Sinatra’s audience, including their massive purchases of the mid-nineties Duets and Duets II, Sinatra’s final albums and by far the best-selling ones of his career? “Old school” is a phrase that one often hears from contemporary college students, almost always signaling high praise. It encompasses durability and authenticity—the way things were back when life was, if not better, then definitely cooler.

Sinatra passes muster on both counts. Durability? When he started singing “The House I Live In,” it had a line describing America as “a dream that’s been a-growing for 150 years.” When Sinatra sang it in 1994 for Duets II, he had to update the line to say: “for more than 200 years.”

As for authenticity, one of Sinatra’s gifts was to let us see him age. He didn’t die young, like Kurt Cobain and Jim Morrison, and he didn’t keep trying to look young, like the aging Elvis. Instead, his voice got deeper and grittier, with all the cracks showing; his hair faded from piled-up and brown to flat and steely and then wispy and white; and his on-stage manner evolved from winsome to brash to sweetly doddering. As Rolling Stone critic Mikal Gilmore wrote, “Sinatra knows enough to surrender to old age, to sing his songs in the voice of an old man stripped of most hopes and all conceits.”

It took until the 1990s for most rock musicians to admit how much Frank Sinatra had influenced them. Sinatra had never put out the welcome mat, of course. In the 1950s he publicly excoriated rock as “brutal, ugly, desperate, vicious” music that was “sung, played, and written for the most part by cretinous goons.”

The passage of time, along with a certain mellowing on Sinatra’s part, eventually made it easier for rock musicians to praise him. In an effusive tribute at the 1994 Grammy Awards ceremony, U2 lead singer Bono said: 

Rock and roll people love Frank Sinatra because Frank Sinatra has got what we want—swagger and attitude…. His voice, tight as a fist, opening at the end of a bar, not on the beat, over it—playing with it, splitting it. Like a jazz man, like Miles Davis. Turning on the right phrase in the right song, which is where he lives, where he lets go, where he reveals himself. His songs are his home, and he lets you in.

Sinatra’s death in 1998 provoked a similar outpouring of tributes from younger artists. Most followed Bono in emphasizing the debt rockers owed Sinatra for introducing a musical persona grounded in sex and swagger, shadowed with a dark sadness. Sinatra had “a voice filled with bad attitude, life, beauty, excitement, a nasty sense of freedom, sex, and a sad knowledge of the ways of the world,” said Bruce Springsteen. Bob Dylan praised Sinatra as “one of the few singers who sang without a mask.” He was “the mountain you have to climb, even if you only get part of the way there.”

For lovers of Sinatra music, the best news in recent years has been the movement of contemporary singers in his direction. In 2015 Dylan recorded Shadows in the Night, a not-bad compilation of Sinatra songs. Annie Lennox also recently released a standards album, joining a long procession that reaches back to Willie Nelson’s 1978 Stardust album and includes records (better left unheard) by Carly Simon, Linda Ronstadt, and Rod Stewart. The best effort of all is British pop king Robbie Williams’s 2001 album, Swing When You’re Winning.

Even more encouraging has been the popularity of such Sinatra-inspired singers as Harry Connick Jr., Diana Krall, Michael Buble, and Seth MacFarlane, artists with rock-star potential who chose a different musical path. My guess is that the tributes written on the 150th or 200th anniversary of Sinatra’s birth will say it was the better path.