Beginning his musical career in the swing era with Harry James and Tommy Dorsey, Sinatra found unprecedented success as a solo artist from the early to mid-1940s after being signed to Columbia Records in 1943. Being the idol of the “bobby soxer’s”, he released his first album, “The Voice of Frank Sinatra” in 1946. His professional career had stalled by the 1950s, but it was reborn in 1953 after he won the Academy Award for Best Supporting Actor for his performance in “From Here To Eternity”.
He signed with Capitol Records in 1953 and released several critically lauded albums. Sinatra left Capitol to found his own record label, Reprise Records in 1961, and toured internationally. He was a founding member of the famed “Rat Pack” and fraternized with celebrities and statesmen, including John F. Kennedy. Sinatra turned 50 in 1965, recorded the retrospective “September of My Years“, starred in the Emmy-winning television special “Frank Sinatra: A Man and His Music”, and scored hits with “Strangers In The Night” and “My Way”.
With sales of his music dwindling and after appearing in several poorly received films, Sinatra retired for the first time in 1971. Two years later, however, he came out of retirement and in 1973 recorded several albums, scoring a Top 40 hit with (Theme From) New York, New York” in 1980. Using his Las Vegas shows as a home base, he toured both within the United States and internationally, until a short time before his death in 1998.
Sinatra also forged a highly successful career as a film actor, winning the Academy Award for Best Supporting Actor, a nomination for Best Actor for “The Man With The Golden Arm”, and critical acclaim for his performance in “The Manchurian Candidate”. He also starred in such musicals as “High Society” and “Guys and Dolls”. Sinatra was honored at the Kennedy Center Honors in 1983 and was awarded the Presidential Medal of Freedom by President Ronald Reagan in 1985 and the Congressional Gold Medal in 1997. Sinatra was also the recipient of eleven Grammy Awards, including the Grammy Trustees Award, Grammy Legend Award, and the Grammy Lifetime Achievement Award.
Born in Hoboken, New Jersey, Sinatra was the only child of Italian immigrants Natalie Della (Garaventa) and Antonio Martino Sinatra, and was raised Roman Catholic. In his book “Try And Stop Me” (p. 218), American publisher and writer Bennett Cerf says that Sinatra's father was a lightweight boxer who fought under the name Marty O'Brien and was a member of the Hoboken fire brigade. Sinatra left high school without graduating, having attended only 47 days before being expelled because of his rowdy conduct. Sinatra's father, often referred to as Marty, served with the Hoboken Fire Department as a Captain. His mother, known as Dolly, was influential in the neighborhood and in local Democratic Party circles, but also ran an illegal abortion business from her home; she was arrested several times and convicted twice for this offense. During the Great Depression, Dolly nevertheless provided money to her son for outings with friends and expensive clothes. In 1938, Sinatra was arrested for carrying on with a married woman, a criminal offense at the time. For his livelihood, he worked as a delivery boy at the Jersey Observer newspaper, and later as a riveter at the Tietjan and Lang shipyard, but music was Sinatra's main interest, and he listened carefully to big band jazz. He began singing for tips at the age of eight, standing on top of the bar at a local nightclub in Hoboken. Sinatra began singing professionally as a teenager in the 1930s, although he learned music by ear and never learned how to read music.
Sinatra got his first break in 1935 when his mother persuaded a local singing group, The Three Flashes, to let him join. With Sinatra, the group became known as the Hoboken Four, and they sufficiently impressed Edward Bowes. After appearing on his show, Major Bowes Amateur Hour, they attracted 40,000 votes and won the first prize - a six month contract to perform on stage and radio across the United States. Sinatra left the Hoboken Four and returned home in late 1935. His mother secured him a job as a singing waiter and MC at the Rustic Cabin in Englewood Cliffs, New Jersey, for which he was paid $15 a week.
On March 18, 1939, Sinatra made a demo recording of a song called “Our Love“, with the Frank Mane band. The record has “Frank Sinatra” signed on the front. The bandleader kept the original record in a safe for nearly 60 years. In June, Harry James hired Sinatra on a one-year contract of $75 a week. It was with the James band that Sinatra released his first commercial record “From the Bottom of My Heart” in July 1939 - US Brunswick No. 8443 and UK Columbia #DB2150.
In November 1939, in a meeting at the Palmer House in Chicago, Sinatra was asked by bandleader Tommy Dorsey to join his band as a replacement for Jack Leonard (the vocalist, not to be confused the comedian Jack E. Leonard), who had recently left to launch a solo career. This meeting was a turning point in Sinatra's career. By signing with Dorsey's band, one of the hottest at the time, he greatly increased his visibility with the American public. Though Sinatra was still under contract with James, James recognized the opportunity Dorsey offered and graciously released Sinatra from his contract. Sinatra recognized his debt to James throughout his life and upon hearing of James' death in 1983, stated: “he (James) is the one that made it all possible.”
On January 26, 1940, Sinatra made his first public appearance with the Dorsey band at the Coronado Theater in Rockford, Illinois. In his first year with Dorsey, Sinatra released more than forty songs, with “I'll Never Smile Again” topping the charts for twelve weeks beginning in mid-July. Sinatra's relationship with Tommy Dorsey was troubled, because of their contract, which awarded Dorsey one-third of Sinatra's lifetime earnings in the entertainment industry. In January 1942, Sinatra recorded his first solo sessions without the Dorsey band (but with Dorsey's arranger Axel Stordahl and with Dorsey's approval). These sessions were released commercially on the Bluebird label. Sinatra left the Dorsey band in late 1942 in an incident that started rumors of Sinatra's involvement with the Mafia. A story appeared in the Hearst newspapers that mobster Sam Giancana coerced Dorsey to let Sinatra out of his contract for a few thousand dollars, and was fictionalized in the book and movie “The Godfather”. According to Nancy Sinatra's biography, the Hearst rumors were started because of Frank's Democratic politics. In fact, the contract was bought out by MCA founder Jules Stein for $75,000.
In May 1941, Sinatra was at the top of the male singer polls in the Billboard and Down beat magazines. His appeal to “bobby soxers, as teenage girls of that time were called, revealed a whole new audience for popular music, which had been recorded mainly for adults up to that time.
On December 30, 1942, Sinatra made a “legendary opening” at the Paramount Theater in New York. When Sinatra returned to the Paramount in October 1944, 35,000 fans caused a near riot outside the venue because they were not allowed in.
During the musicians’ strike of 1942 - 44, Columbia re-released Harry James and Sinatra's version of “All or Nothing At All” (music by Arthur Altman and lyrics by Jack Lawrence), recorded in August 1939 and released before Sinatra had made a name for himself. The original release did not even mention the vocalist's name. When the recording was re-released in 1943 with Sinatra's name prominently displayed, the record was on the best–selling list for 18 weeks and reached number 2 on June 2nd, 1943.
Sinatra signed with Columbia on June 1st, 1943, as a solo artist, and he initially had great success, particularly during the musicians’ strike. Although no new records had been issued during the strike, he had been performing on the radio (on Your Hit parade), and on stage. Columbia wanted to get new recordings of their growing star as fast as possible, so Sinatra convinced them to hire Alec Wilder as arranger and conductor for several sessions with a vocal group called the Bobby Tucker Singers. These first sessions were on June 7th, June 22nd, August 5th, and November 10th, 1943. Of the nine songs recorded during these sessions, seven charted on the best-selling list.
Sinatra did not serve in the military during World War II. On December 11th, 1943, he was classified 4-F (“Registrant not acceptable for military service“) for a perforated eardrum by his draft board. Additionally, an FBI report on Sinatra, released in 1998, showed that the doctors had also written that he was a “neurotic” and “not acceptable material from a psychiatric standpoint.” This was omitted from his record to avoid undue unpleasantness for both the selectee and the induction service. Active-duty servicemen, like journalist William Manchester, said of Sinatra, “I think Frank Sinatra was the most hated man of World War II, much more than Hitler“, because Sinatra was back home making all of that money and being shown in photographs surrounded by beautiful women. His exemption would resurface throughout his life and cause him grief when he had to defend himself. There were accusations, including some from noted columnist Walter Winchell, that Sinatra paid $40,000 to avoid the service - but the FBI found no evidence of this.
In 1945, Sinatra co-starred with Gene Kelly in “Anchors Aweigh”. That same year, he was loaned out to RKO to star in a short film titled “The House I Live In”. Directed by Mervyn LeRoy, this film on tolerance and racial equality earned a special Academy Award shared among Sinatra and those who brought the film to the screen, along with a special Golden Globe for “Promoting Good Will“. 1946 saw the release of his first album, “The Voice of Frank Sinatra”, and the debut of his own weekly radio show. By the end of 1948, Sinatra felt that his career was stalling, something that was confirmed when he slipped to No. 4 on Down Beat’s annual poll of most popular singers. The year 1949 saw an upswing, as Frank co-starred with Gene Kelly in “Take Me Out To The Ball Game”. It was well received critically and became a major commercial success. That same year, Sinatra teamed up with Kelly for a third time in “On The Town”.
After a two year absence, Sinatra returned to the concert stage on January 12th, 1950, in Hartford, Connecticut. His voice suffered and he experienced hemorrhaging of his vocal cords on stage at the Copacabana on April 26th, 1950. Sinatra's career and appeal to new teen audiences declined as he moved into his mid-30s.
This was a period of serious self-doubt about the trajectory of his career. In February 1951, he was walking through Times Square, past the Paramount theatre, keystone venue of his earlier phenomenal success. The Paramount marquee glowed in announcement of Eddie Fisher in concert. Swarms of teen-age girls had gathered in frenzy, swooning over the current singing idol. For Sinatra this public display of enthusiasm for Fisher validated a fear he had harbored in his own mind for a long time. The Sinatra star had fallen; the shouts of “Frankieee” were echoes of the past. Agitated and disconsolate he rushed home, closed his kitchen door, turned on the gas and laid his head on the top of the stove. A friend returned to the apartment not long after to find Sinatra lying on the floor sobbing out the melodrama of his life, proclaiming his failure was so complete he could not even commit suicide.
In September 1951, Sinatra made his Las Vegas debut at the Desert Inn. A month later, the second season of “The Frank Sinatra Show” began on CBS Television. Ultimately, Sinatra did not find the success on television for which he had hoped. The persona he presented to the TV audience was not that of a performer easily welcomed into homes. He projected an arrogance not compatible with the type of cozy congeniality that played well on the small screen. Columbia and MCA dropped him in 1952.
The rebirth of Sinatra's career began with the eve-of-Pearl Harbor drama “From Here To Eternity” (1953), for which he won an Academy Award for Best Supporting Actor. This role and performance marked a turnaround in Sinatra's career: after several years of critical and commercial decline, becoming an Oscar-winning actor helped him regain his position as the top recording artist in the world. Also in 1953, Sinatra starred in the NBC radio program Rocky Fortune. His character, Rocko Fortunato (aka Rocky Fortune) was a temp worker for the Gridley Employment Agency who stumbled into crime-solving by way of the odd jobs to which he was dispatched. The series aired on NBC radio Tuesday nights from October 1953 to March 1954, following the network's crime drama hit “Dragnet”. During the final months of the show, just before the 1954 Oscars, it became a running gag that Sinatra would manage to work the phrase “from here to eternity” into each episode, a reference to his Oscar-nominated performance.
In 1953, Sinatra signed with Capitol Records, where he worked with many of the finest musical arrangers of the era. Through the late fifties, Sinatra frequently criticized rock and roll music, much of it being his reaction to rhythms and attitudes he found alien. In 1958 he lambasted it as “sung, played, and written for the most part by cretinous goons. It manages to be the martial music of every side-burned delinquent on the face of the earth.
Sinatra started the 1960s as he ended the 1950s. His first album of the decade, “Nice ’n’ Easy”, topped Billboard’s chart and won critical plaudits. Sinatra grew discontented at Capitol and decided to form his own label, Reprise Records. His first album on the label, “Ring-A-Ding-Ding!” (1961), was a major success, peaking at No.4 on Billboard and No.8 in the UK.
From his youth, Sinatra displayed sympathy for African Americans and worked both publicly and privately all his life to help them win equal rights. He played a major role in the desegregation of Nevada hotels and casinos in the 1960s. On January 27, 1961, Sinatra played a benefit show at Carnegie Hall for Martin Luther King, Jr. and led his fellow Rat Pack members and Reprise label mates in boycotting hotels and casinos that refused entry to black patrons and performers. He often spoke from the stage on desegregation and repeatedly played benefits on behalf of Dr. King and his movement.
On September 11 and 12, 1961, Sinatra recorded his final songs for Capitol. Sinatra's first live album, “Sinatra At The Sands”, was recorded during January and February 1966 at the Sands Hotel and Casino in Las Vegas.
In June 1965, Sinatra, Sammy Davis Jr., and Dean Martin played live in Saint Louis to benefit Dismas House. The Rat Pack concert was broadcast live via satellite to numerous movie theaters across America. Released in August 1965 was the Grammy Award–winning album of the year, “September of My Years”, containing the single “It Was A Very Good Year”, which won the Grammy Award for Best Vocal Performance, Male in 1966. A career anthology, “A Man and His Music”, followed in November, winning Album of the Year at the Grammys in 1966. The TV special, “Frank Sinatra: A Man and His Music”, garnered both an Emmy award and a Peabody Award.
Throughout his life, Sinatra had mood swings and bouts of depression. Solitude and unglamorous surroundings were to be avoided at all cost. He struggled with the conflicting need “to get away from it all, but not too far away.” Although beloved as a hero by his hometown of Hoboken, Frank Sinatra rarely visited it. According to one account, Sinatra returned once in 1948 to celebrate the election of Hoboken's first Italian mayor and was not well received by the crowd. He stated he would never come back, and in fact did not return until 1984, to appear with Ronald Reagan.
Sinatra garnered considerable attention due to his alleged personal and professional links with organized crime, including figures such as Carlo Gambino, Sam Giancana, Lucky Luciano and Joseph Fischetti. The FBI kept records amounting to 2,403 pages on Sinatra. With his alleged Mafia ties, his ardent New Deal politics and his friendship with John F. Kennedy, he was a natural target for J. Edgar Hoover’s FBI. The FBI kept Sinatra under surveillance for almost five decades beginning in the 1940s. The documents include accounts of Sinatra as the target of death threats and extortion schemes. They also portray rampant paranoia and strange obsessions at the FBI and reveal nearly every celebrated Sinatra foible and peccadillo.
For a year Hoover investigated Sinatra's alleged Communist affiliations, but found no evidence. The files include his rendezvous with prostitutes, and his extramarital affair with Ava Gardner, which preceded their marriage. Celebrities mentioned in the files are Dean Martin, Marilyn Monroe, Peter Lawford, and Giancana's girlfriend, singer Phyllis McGuire. The FBI's secret dossier on Sinatra was released in 1998 in response to Freedom of Information Act requests.
The released FBI files reveal some tantalizing insights into Sinatra’s lifetime consistency in pursuing and embracing seemingly conflicting affiliations. But Sinatra’s alliances had a practical aspect. They were adaptive mechanisms for behavior motivated by self-interest and inner anxieties. In September 1950 Sinatra felt particularly vulnerable. He was in a panic over his moribund career and haunted by the continual speculations and innuendos in circulation regarding his draft status in World War II. Sinatra was scared, his career had sprung a leak. In a letter dated September 17th, 1950, to Clyde Tolson, Deputy FBI Director, Sinatra offered to be of service to the FBI as an informer. An excerpted passage from a memo in FBI files states that Sinatra “feels he can be of help as a result of going anywhere the Bureau desires and contacting any people from whom he might be able to obtain information. Sinatra feels as a result of his publicity he can operate without suspicion…he is willing to go the whole way.” The FBI declined his assistance.
Sinatra began to show signs of dementia in his last years. After a heart attack in February 1997, he made no further public appearances. After suffering another heart attack, he died at 10:50 p.m. on May 14th, 1998, at the Cedars-Sinai Medical center, with his wife, Barbara, by his side. He was 82 years old. Sinatra's final words, spoken after Barbara encouraged him to “fight” as attempts were made to stabilize him, were, “I'm losing.” The official cause of death was listed as complications from dementia, heart and kidney disease, and bladder cancer. His death was confirmed by the Sinatra family on their website with a statement accompanied by a recording of the singer's version of “Softly As I Leave You.” The next night the lights on the Las Vegas Strip were dimmed for 10 minutes in his honor and the lights on the Empire State Building in New York were turned blue.
On May 20th, 1998, Sinatra's funeral was held, with 400 mourners in attendance and hundreds of fans outside. A private ceremony was held later that day at St. Theresa's Catholic Church in Palm Springs. Sinatra was buried following the ceremony next to his parents in section B-8 of Desert Memorial Park in Cathedral City, a quiet cemetery on Ramon Road where Cathedral City meets Rancho Mirage and near his compound, located on Rancho Mirage's tree-lined Frank Sinatra Drive. The words “The Best Is Yet to Come” are imprinted on Sinatra's grave marker.
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