Frank Sinatra

• 1. Introduction

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  Francis Albert Sinatra weighed 13.5 pounds when he was born on the 12th of December 1915, in a tenement at 415 Monroe Street in Hoboken, New Jersey. The delivery required forceps, which scarred his left cheek and neck and left lifelong damage to his left eardrum. He was the only child of Italian immigrants, and a childhood operation and cystic acne would scar him further. This skinny, scarred kid from Hoboken would become known as the Chairman of the Board and Ol' Blue Eyes. Robert Christgau, the American music critic, called him the greatest singer of the 20th century. Sinatra sold an estimated 150 million records and won 11 Grammy Awards and an Academy Award. He died on the 14th of May 1998. How did a boy expelled after 47 days of high school come to command a record label he sold for an estimated 80 million dollars? How did a singer dropped by his label in 1952 climb back to the top of his profession? And why did he detest singing the song that became his signature?

• 2. The Mother And The Boxer

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  Natalina "Dolly" Garaventa, Sinatra's mother, was from Genoa in Liguria, and biographers believe she was the dominant force in shaping her son's personality and self-confidence. She became influential in Hoboken and in local Democratic Party circles. Barbara Sinatra, his fourth wife, would later claim that Dolly "knocked him around a lot" when he was a child. During the Great Depression, Dolly gave her son money for outings and expensive clothes, and neighbors called him the "best-dressed kid in the neighborhood".

  Marty Sinatra, the boy's father, was an illiterate bantamweight boxer from Sicily who later worked his way up to captain at the Hoboken Fire Department. Because he could not read, Marty stressed a "complete and full" education and pushed his son toward becoming a civil engineer at the Stevens Institute of Technology. Sinatra had other ideas. He spent time at his parents' tavern, working on homework and singing for spare change. For his 15th birthday, his uncle Domenico gave him a ukulele, which he played at family gatherings, idolizing Bing Crosby. He left A. J. Demarest High School without graduating and lasted only 11 months at Drake Business School.

• 3. Bobby Soxers And A Riot

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  Forty thousand votes won Sinatra his first taste of fame. In 1935 his mother persuaded a local group called the 3 Flashes to let him join, and as the "Hoboken Four" they passed an audition for the Major Bowes Amateur Hour. They each earned 12.50 dollars and took first prize, a six-month contract performing across the country. Sinatra quickly became the lead singer and drew most of the attention from the girls.

  The Paramount Theatre in New York witnessed the phenomenon that newspapers named "Sinatramania" after his opening there on the 30th of December 1942. Jack Benny said, "I thought the goddamned building was going to cave in. I never heard such a commotion." His fans were teenage girls known as bobby soxers, and within weeks some 1,000 Sinatra fan clubs were reported across the United States. When he returned to the Paramount in October 1944, only 250 people left the first show, and 35,000 fans outside caused a near riot, remembered as the Columbus Day Riot. George Evans, his publicist, shaped the image of a shy, vulnerable Italian-American who made good. Devotees bribed hotel maids to touch his bed and stole the clothing he wore.

• 4. Dorsey And The Turning Point

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  On the 26th of January 1940, Sinatra made his first appearance with the Tommy Dorsey band at the Coronado Theatre in Rockford, Illinois, opening with "Stardust". Dorsey recalled, "He was just a skinny kid with big ears. I used to stand there so amazed I'd almost forget to take my own solos." Dorsey became a father figure, and Sinatra copied his mannerisms, his perfectionism, even his hobby of toy trains. Sinatra later said, "The only two people I've ever been afraid of are my mother and Tommy Dorsey."

  The trombone taught Sinatra to sing. Dorsey's exceptional breath control on the instrument influenced his vocal phrasing, and Sinatra began swimming and holding his breath underwater while thinking of lyrics to build his lungs. On the 19th of January 1942, Dorsey finally let him record solo songs including "Night and Day", with Axel Stordahl arranging. Hearing the playbacks, Sinatra was astounded, and Stordahl recalled, "I think this was a turning point in his career." But Sinatra's contract gave Dorsey 43 percent of his lifetime earnings. A legal battle was settled in August 1942, and on the 3rd of September Dorsey reportedly said, "I hope you fall on your ass." The two men never reconciled.

• 5. From The Top To The Bottom

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  Ten million records a year flowed from Sinatra at his peak. By 1946 he was performing on stage up to 45 times a week, singing up to 100 songs daily and earning up to 93,000 dollars a week. That year his debut album, The Voice of Frank Sinatra, reached No. 1 on the Billboard chart. He even indulged his love of conducting, becoming the conductor at Columbia for six of Alec Wilder's compositions.

  The death of George Evans in January 1950 marked the start of a brutal collapse. Reports broke of his affair with Ava Gardner and the destruction of his marriage to Nancy. He had to cancel five days at the Copa after a throat hemorrhage, and he borrowed 200,000 dollars from Columbia to pay back taxes after MCA refused. At a concert at Chez Paree in Chicago, only 150 people turned up in a 1,200-seat venue. Mitch Miller, the Columbia A&R executive, claimed he "couldn't give away" Sinatra records. Columbia and MCA both dropped him in 1952. Journalist Burt Boyar observed, "Sinatra had had it. From the top to the bottom in one horrible lesson."

• 6. Maggio And The Comeback

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  Harry Cohn, the boss of Columbia Pictures, was inundated with appeals to let Sinatra play "Maggio" in From Here to Eternity. The 1953 film by Fred Zinnemann followed three soldiers, played by Burt Lancaster, Montgomery Clift, and Sinatra, in Hawaii before the attack on Pearl Harbor. Clift became a close friend, and Sinatra said he "learned more about acting from him than anybody I ever knew before". His win for the Academy Award for Best Supporting Actor restored his standing as the top recording artist in the world. The Los Angeles Examiner called him "simply superb, comical, pitiful, childishly brave, pathetically defiant".

  Guys and Dolls and High Society followed, the latter earning Sinatra a reported 250,000 dollars and grossing over 13 million dollars at the box office. He won a Golden Globe Award for his role in Pal Joey in 1957, and Santopietro considered his rendition of "The Lady Is a Tramp" the finest moment of his film career. He earned an Academy Award nomination for Best Actor as a heroin addict in The Man with the Golden Arm in 1955. During the making of Not as a Stranger that same year, Sinatra got drunk with Robert Mitchum and Broderick Crawford and trashed director Stanley Kramer's dressing room.

• 7. Riddle And The Concept Album

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  On the 30th of April 1953, back from filming in Hawaii, Sinatra returned to KHJ studios for his first recording session with Nelson Riddle, an arranger who served as Nat King Cole's musical director. After recording "I've Got the World on a String", Sinatra exclaimed, "I'm back, baby, I'm back!" He came to call Riddle "the greatest arranger in the world", and Riddle said of him, "his taste is so impeccable. There is still no one who can approach him."

  The 12-inch LP let Sinatra turn each track into a kind of chapter. In 1955 he released In the Wee Small Hours, which Charles Granata calls the first of his concept albums to make a "single persuasive statement", with a melancholy mood. Songs for Swingin' Lovers! followed in March 1956, featuring "I've Got You Under My Skin", which reportedly took 22 takes. His split with Ava Gardner in the fall of 1953 deepened his ballads, and Riddle saw her influence in songs like "I'm a Fool to Want You". Frank Sinatra Sings for Only the Lonely, a stark collection of saloon songs, spent 120 weeks on the Billboard chart in 1958. The next year, Come Dance with Me! won the Grammy Award for Album of the Year.

• 8. His Own Label And His Way

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  Reprise Records promised its artists creative control and eventual complete ownership of their work, including publishing rights. Sinatra founded the label after growing discontented at Capitol, and it became a music industry powerhouse he later sold for an estimated 80 million dollars. His first Reprise album, Ring-a-Ding-Ding!, peaked at No. 4 in 1961. He collaborated with Count Basie on Sinatra-Basie and reunited with Riddle for The Concert Sinatra, featuring a 73-piece symphony orchestra. September of My Years won the Grammy Award for best album of the year in 1965.

  Paul Anka wrote "My Way" with Sinatra in mind, using the melody of the French "Comme d'habitude". Sinatra recorded it in one take just after Christmas 1968, yet it charted only at No. 27 in the United States. It stayed in the UK charts for 122 weeks, a record still standing in 2015, and NPR notes it has become one of the most requested songs at funerals. Sinatra told songwriter Ervin Drake that he "detested" the song, fearing audiences would think it a "self-aggrandizing tribute". He announced his retirement in June 1971, closing with "Angel Eyes" and the line, "'Scuse me while I disappear," before the spotlight went dark. He returned two years later with the album Ol' Blue Eyes Is Back, and in 1995 the Empire State Building glowed blue to mark his 80th birthday.