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Saturday, December 12, 2015, marks what would have been Frank Sinatra’s 100th birthday. Born in Hoboken, New Jersey, in 1915, he rose from humble beginnings to become the greatest entertainer of the twentieth century. Anyone who delves into the so-called “Great American Songbook” owes a debt to Sinatra. He didn’t write the songs, but he used the force of his voice and his powerful personality to make them his own.

As a human being, though, to say that Sinatra was “flawed” is a bit of an understatement. He contained multitudes. He was tough and tender, mean and romantic, loyal and unforgiving, good and bad. He could turn his emotions up to 11 at the drop of a snap-brimmed hat, and there are many stories of one-time friends who crossed Sinatra and earned his everlasting hatred.

But with Sinatra, you have to take the good with the bad. It’s like the episode of “Star Trek” where the transporter splits the captain into two people: good Kirk and bad Kirk. Bad Kirk is a total dick. Good Kirk is a nice guy, but he lacks the balls to make the tough decisions a captain has to make. To be an effective commander, Kirk needs both sides of his personality.

Sinatra was like that. He was a smoldering cauldron of emotions: resentment, anger, envy, loneliness. He could also be incredibly giving, although always on his own terms. When the volcano inside him erupted in his ordinary life, the results were often not pretty. When he channeled that intense emotional life into his singing, the results could be transcendent. His artistry came with a price.

I can vividly remember when I became a Frank Sinatra fan. I was attending college in Los Angeles, living in an old apartment building on Vermont Avenue. My tiny room smelled of leaking gas and roach powder.

Shabby as it was, the place had its strong points. Right across from the front entrance was Benjy’s Liquor, and Benjy never carded. And the building had a big expansive roof, where I could sit on a late afternoon, watch the sun set over Los Angeles, drink the beer I had bought at Benjy’s, and listen to KROQ.

KROQ was Los Angeles’ “new wave” station. It played artists like the Plimsouls, XTC, Sparks, and Split Enz. It was not in the habit of playing Frank Sinatra. Yet one evening I was sitting on the roof, drinking a beer as the setting sun turned the sky the color of an orange popsicle, and the DJ played a song I recognized from my youth—the title track to Come Fly with Me. My Dad had the album. The song was brassy and upbeat, with muted trumpets kicking things off, and Frank singing about heading off to “llama land, where a one-man band, will toot his flute for you.” It hovered just the right side of self-parody. It also made me feel good hearing it. The next day I headed off to the used record stores on Fairfax Avenue and I bought a copy of the album. I still have it.

That was the beginning of my Sinatra fandom. The next album I bought was Sinatra’s Swingin’ Session!!!, an album so swingtastic it required three exclamation points in its title. I found out later that this was the last album Sinatra had done for Capitol Records. The story goes that Sinatra walked into the studio and told arranger Nelson Riddle to pick up the tempo for all the numbers, without even hearing them. The album does have a rollicking pace, and the original vinyl version clocks in at less than 30 minutes. It does swing, though.

After graduating from college I returned to the East Coast, and I began dipping into my dad’s Sinatra albums. He had a copy of A Swingin’ Affair!, another great collaboration with Riddle. Some friends of my parents had left it behind after a party. (Their name was still written on the album.) Once I moved to Boston, I started buying more albums. One of the first was a collection called This is Sinatra!, which introduced me to the brassy charms of “I’ve Got the World on a String,” still one of my favorite Sinatra songs, and one of the first collaborations with Riddle.

I also bought a copy of Songs for Swingin’ Lovers! It was one of the cheap reissues that Capitol released in the early 1980s. I didn’t find out until years later that the label dropped songs from these new versions to save money, probably to make pressing them cheaper. Songs for Swingin’ Lovers! originally had 15 tracks. Mine had a mere dozen. Among the missing were “Pennies from Heaven” and “Makin’ Whoopee.” Even shortened, the album worked. The first time my future wife visited my apartment, I threw Swingin’ Lovers on the turntable. She was impressed by my savoir faire, or whatever it was. When we got married, our first song was Sinatra’s version of “More.”

All of which is a long way to say, happy birthday, Frank.

I wrote the following piece as part of a book proposal that never got off the ground. I thought the occasion of Sinatra’s 100th would be a good time to share it.

“He’s hot, he’s sexy, and he’s dead.”

Rolling Stone once used that line for a cover story about Jim Morrison. They could use it today to describe Frank Sinatra. Since his death in 1998, the legendary vocalist has appeared in slick ads for Jack Daniels. He provided the soundtrack (and the style) for vodka ads featuring Sean “Diddy” Coombs. He has become an avatar of cool for the hip-hop generation, the Original Gangsta. HBO recently ran a two-part series about Sinatra, part of the build-up to the commemoration of what would have been Sinatra’s 100th birthday on December 12, 2015.

“Frank Sinatra was the 20th century,” said Bono, vocalist for U2, when he saluted the still-living legend in 1994. “He was modern; he was complex; he had swing and attitude. He was the big bang of pop.” Bono knew what he was talking about. Sinatra is arguably the greatest entertainer of the 20th century. Yet he came dangerously close to becoming little more than a footnote in musical history, just one of the strange fads that appeared during World War II. During late 1940s and early 1950s, Sinatra watched his career disintegrate. His label and movie studio dropped him, his audiences grew up and stayed home, and his voice failed. It could all have ended then, not with some swing but with a whimper, and we would have never heard Sinatra’s work with Nelson Riddle, or great albums like Songs for Swingin’ Lovers!

Fortunately for Sinatra and for musical history, Capitol Records came calling. Even more important, the label decided to pair Sinatra with arranger Nelson Riddle. On the surface, the two men seemed remarkably similar. Both hailed from New Jersey, the only children of dominating mothers. Both emerged from the big band era and spent time with Tommy Dorsey’s band. In reality, though, Sinatra/Riddle was an unlikely pairing. Sinatra was—well, Frank Sinatra. He was a hot-tempered boozer and brawler who wore his nerves on his sleeve. Riddle was more subdued (although he did father a child out of wedlock with singer Rosemary Clooney). He was quiet, brooding and introspective, with a sardonic sense of humor produced during a grim childhood. “We didn’t feel the Depression at all, because my father created his own Depression,” he once said. “It was all the same to us because we were already in a depressed state by the time the Depression got there.” Riddle was also a musical genius with a knack for surrounding vocalists with artful, playful arrangements. By the time Capitol teamed him with Sinatra, Riddle had already had arranged hits for Nat King Cole and others, but he found his greatest musical collaborator in Sinatra. “The man himself somehow draws everything out of you,” Riddle once said. “And I always felt that my rather placid disposition had a beneficial effect on him. I was able to calm him down sometimes. He would start snapping at somebody and I would say, ‘Come on, pal, what’s the point of doing that?’ He’d give me a hard look, then he’d stop.”

Riddle never became part of Sinatra’s high-living Rat Pack, but he played a central role in the singer’s life. He helped create Sinatra forge a signature sound that defined, in its way, a portion of the mid-twentieth century. Their collaboration created “one of the greatest bodies of music in all of American popular culture,” wrote musicologist Will Friedwald in his book about Sinatra’s recordings. “In truth virtually all the Sinatra-Riddle albums are masterpieces, their collaboration being sanctified from the first downbeat counted off at the first session onward.”

And it almost never happened.

Frank Sinatra was fast approaching rock bottom when he went out on the stage at the Copacabana for the last show on April 26, 1950.

The bobby soxers who had shrieked for Frankie were long gone. George Evans, the press agent whose behind-the-scenes manipulation of those bobby soxers had helped turn Frankie into the biggest thing in music, had died back in January. Frank’s marriage to wife Nancy, strained after years of infidelities, finally blew following the revelations of his affair with actress Ava Gardner. His record sales were in free fall. MGM’s Louis B. Mayer had dumped him.

Things got even worse for the Voice at the Copa. Sometime around 2:00 a.m. that morning, Sinatra approached the mike to start his final show of the night. He opened his mouth to sing—and nothing came out. “Just dust,” he said. The small audience stared at Sinatra. Sinatra stared back at them. “I was never so panic-stricken in my life,” he said. Finally, the singer managed to whisper “Good night” and walked offstage.

It hadn’t been so long since Frank Sinatra had been on top of the world. He had come a long way from Hoboken, where he was the only son of a force of nature named Dolly Sinatra and Antony Martin Sinatra, her sometimes dock worker/bartender/boxer husband. Born in Hoboken on December 12, 1915, Francis Albert Sinatra decided at an early age he wanted to be a singer. The story goes that he attended a Bing Crosby show one night and told his girlfriend (and future wife) Nancy Barbato, “Someday that will be me up there.” He sang and toured with a local trio that made a splash on the Major Bowes Amateur Hour as the Hoboken four, but he got his big break as a singing waiter at the Rustic Cabin, a roadhouse in Englewood, New Jersey. One night trumpeter and bandleader Harry James came in to size up the local talent. “He’d sung only eight bars when I felt the hairs on the back of my neck rising,” James recollected about the first time he heard Sinatra. “I knew he was destined to be a great vocalist.” Sinatra signed with James in February 1939, at $75 a week.

He didn’t stay with James for long. By the end of the year he was aiming higher—at Tommy Dorsey, leader of the number one band in the country. In January 1940 Sinatra left the struggling James band—Harry tore up the contract—and signed with Dorsey for $125 week. The next year Billboard picked Sinatra as the nation’s top vocalist. He learned a lot from Dorsey, most notably by watching how the bandleader played his trombone, especially how he controlled his breathing to create the smooth legato for which he was known. “He would take a musical phrase and play it all the way through seemingly without breathing for 8, 10, maybe 16 bars,” Sinatra said in an article for Life magazine in 1965. “Why couldn’t a singer do that, too?” he wondered. Sinatra also listened to the violin playing of Jascha Heifetz, the way the violinist played without taking a break in the melody line. “It was my idea to make my voice work in the same way as a trombone or a violin—not sounding like them, but ‘playing’ the voice like those instruments.”

Another thing Sinatra learned was the value of the microphone. “Many singers never learned to use one,” he said. “They never understood, and still don’t, that a microphone is their instrument.” Sinatra understood that perfectly well, and had a keen sense of the way amplification offered the singer an almost intimate bond with the listener.

But although Sinatra owed a lot to Dorsey, it wasn’t long before he was straining at the leash. Dorsey may have been known as “the Sentimental Gentleman of Swing,” but in reality he was a tough-as-nails taskmaster with an explosive temper. Long before Sinatra’s three-year contract was up, the ambitious singer decided he wanted to strike out on his own. One motivation was an overture by Manie Sacks of Columbia Records, who encouraged Sinatra to record solo for his label. Unlike James, Dorsey wasn’t quite so willing to tear up a contract. He insisted on extracting plenty of cash in exchange for Sinatra’s freedom. The deal sparked rumors that the mob had played a role (as portrayed in fictionalized form in The Godfather), and it left a good deal of bitterness behind. “I hope you fall on your ass,” Dorsey told his now ex-singer.

Dorsey got his wish, but it took almost a decade for it to happen. First, Sinatra ascended to dizzying heights of fame and adulation, starting with a gig opening for the Benny Goodman band at New York’s Paramount Theater on December 20, 1942. By then the young women known as bobby soxers had embraced the young Sinatra with an emotional frenzy. Something about the strangely vulnerable (on stage, anyway), skinny young man with the oversized bow ties, the aching voice and the blue eyes set them ablaze. His gig at the Paramount became a sensation. Singer Peggy Lee said there was something “electric” when Sinatra came on stage. “We used to lean out the windows of the dressing room to see the crowd of swooners, like swarms of bees down there in the street, just waiting for the sight of Frankie,” she said.

Sinatra’s press agent, George Evans, claimed some of the credit, saying he paid bobby soxers to swoon and cause a scene. But anyone could see that Sinatra’s appeal was more than just flackery. Young women screamed his name, mobbed him, and nearly strangled him when they grabbed at his bow ties. His voice was full of yearning; they yearned for him. Sinatramania grew and grew, as he hosted Your Hit Parade on radio and appeared in films and on stage. Sinatra, who had a perforated eardrum that kept him from being drafted, attributed some of the hysteria to his role as the stand-in for all the young men who were overseas.

Sinatra signed with Columbia Records in 1943, but a musicians’ strike kept him from recording new material with a band. To get around the strike, Sinatra recorded some a Capella records and even charted a hit single with the re-release of the Harry James version of “All or Nothing at All.” When the recording ban finally ended 1944, Sinatra embarked on his first great musical partnership, with arranger/conductor Axel Stordahl. The two had met in Dorsey’s band, where Stordahl did some arranging. The bald, pipe-smoking, tweed-wearing Stordahl looked like a music professor, and he wrapped Sinatra’s voice in almost classical arrangements. John Rockwell described the recordings they did together as “a wash of strings and lush, neo-Tchaikovskian arrangements to accompany Sinatra’s gorgeous, lyrical, intimate, introspective ballad singing.” On the strength of his work with Stordahl, Sinatra earned the nickname of “The Voice.” But, let’s face it; those recordings were a little boring.

The bobby soxers who swarmed his live performances were anything but bored. Things peaked in October 1944 and the “Columbus Day Riots. Sinatra was booked for a return engagement at New York’s Paramount Theater, the same venue where he had launched his solo career. On October 11, a school holiday, the bobby soxers were waiting for him in droves, perhaps as many as 10,000, standing in long lines that stretched down the street and around the block. Trouble broke out when the fans inside for the first show refused to give up their seats for those waiting outside.

“For Sinatra that stand at the Paramount was a kind of culmination, the final explosive orgy of his cult of youth,” wrote James Kaplan in his 2010 biography. He was still popular, but he had apparently peaked. His young followers were growing up. The war was ending, and a resumption of normal life beckoned.

Sinatra did what he could to hasten his decline. More and more he became a topic in gossip columns—if he wasn’t slugging newspaper columnists, he was squiring women not his wife around town. It was not good for his image. His very public affair with smoldering actress Ava Gardner finally put an end to his marriage with Nancy, while his left-leaning politics caught the attention of the FBI.

The musical front was just as rocky. In 1950, producer Mitch Miller took over as chief of recording at Columbia Records. Miller’s work with Sinatra would mark the nadir of the singer’s career, culminating with the now infamous “Mama Will Bark,” in which Sinatra shared vocal duties with the Swedish model Dagmar and a man howling like a dog. (Of Miller, Sinatra biographer John Rockwell wrote, “His taste was so silly that he seems in retrospect to have been placed on this planet for the express purpose of heralding rock’s cleansing passion.”) Miller’s arrival at Columbia’s helm was the beginning of the end for Sinatra’s stint at the label. He and Columbia finally parted ways in 1952.

Things were about to get better.

Capitol Records was founded in 1942 by two songwriters—Johnny Mercer and Buddy DeSylva—and one record store owner—Glenn Wallichs, who owned Music City in Hollywood.

Financed by $25,000 of Mercer’s money, the fledgling label managed to survive the war years despite a lack of shellac to make records and the recording ban that had also hobbled Sinatra’s start with Columbia. By the time Sinatra signed in 1953, Capitol was going strong.

A lot of people took credit for getting Sinatra to his new label. Singer Jo Stafford, who recorded for Capitol, said she suggested to Dave Dexter, Jr., a producer at Capitol, that he sign Sinatra. Dexter went to see Sinatra perform, was sufficiently impressed by what he heard (the singer had bounced back from his throat woes), and gave the label a favorable report.

Alan Livingston, Capitol’s A&R vice president, remembered it differently. Livingston said he received a call from Sinatra’s new agent, Sam Weisbord of William Morris, to see if Capitol was interested. “Sinatra had hit bottom, and I mean bottom,” Livingston recalled for author Charles L. Granata. “He couldn’t get a record contract, and he literally, at that point, could not get a booking in a nightclub. It was that bad—he was broke, and in a terrible state of mind.”

Livingston signed him anyway.

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