Beginning his musical career in the swing era with Harry James and Tommy Dorsey, Sinatra became a successful solo artist in the early to mid-1940s, being the idol of the "bobby soxers." His professional career had stalled by the 1950s, but it was reborn in 1954 after he won the Academy Award for Best Supporting Actor.
He signed with Capitol Records and released several critically lauded albums (such as In the Wee Small Hours, Songs for Swingin' Lovers, Come Fly with Me, Only the Lonely and Nice 'n' Easy). Sinatra left Capitol to found his own record label, Reprise Records (finding success with albums such as Ring-A-Ding-Ding, Sinatra at the Sands and Francis Albert Sinatra & Antonio Carlos Jobim), toured internationally, was a founding member of the Rat Pack and fraternized with celebrities and presidents, including President 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."
Sinatra attempted to weather the changing tastes in popular music, but with sales of his music dwindling, and after appearing in several poorly received films, he retired in 1971. Coming out of retirement in 1973, he recorded several albums; scored a Top 40 hit with "(Theme From) New York, New York" in 1980; and toured both within the United States and internationally until a few years before his death in 1998.
Sinatra was born in Hoboken, New Jersey, the only child of Italian/Sicilian immigrants Natalie Della (née Garaventa) and Antonio Martino Sinatra. He left high school without graduating, having attended only 47 days before being expelled due to his rowdy conduct. 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. Frank, himself, was arrested for carrying on with a married woman, an illegal offense at the time.
1935–40: Start of career, work with James and Dorsey
Sinatra's first cousin, Ray Sinatra, had an orchestra and his own network radio program ("Cycling the Kilocycles") in the mid-1930s, but Ray and Frank did not work together. Instead, he 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 4 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. 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 #8443 and UK Columbia #DB2150.
Fewer than 8,000 copies of "From the Bottom of My Heart" (Brunswick #8443) were sold, making the record a very rare find that is sought after by both Sinatra and record collectors worldwide. Sinatra released ten commercial tracks with James through 1939, including "All or Nothing At All" which had weak sales on its initial release but then sold millions of copies when re-released by Columbia at the height of Sinatra's popularity a few years later.
In November 1939, in a meeting at the Palmer House in Chicago, IL, Sinatra was asked by bandleader Tommy Dorsey to join his band as a replacement for Jack Leonard who had recently left to launch a solo career. This meeting represented a turning point in Sinatra's career since by signing with Dorsey's band, one of the hottest bands at the time, he would achieve incredible visibility with the American public. Though Sinatra was still under contract with James, James recognized the opportunity Dorsey offered to Sinatra and graciously released him from his contract. Sinatra remained indebted 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, IL. In his first year with Dorsey, Sinatra released more than forty songs, with "I'll Never Smile Again" topping the charts for twelve weeks in mid-July.
Due to a punitive contract that awarded Dorsey ⅓ of Sinatra's lifetime earnings in the entertainment industry, Sinatra's relationship with Tommy Dorsey was tenuous. 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 late in 1942 in an incident that started rumors of Sinatra's mob involvement. According to contemporary Hearst newspaper accounts at the time mobster Sam Giancana convinced Dorsey to let Sinatra out of his contract for a few thousand dollars through coercion, an event famously fictionalized in the movie The Godfather. According to Nancy Sinatra's biography, the Hearst rumors were started because of Frank's Democratic politics. In actuality, the contract was bought out by MCA founder Jules Stein for the princely sum of $75,000.
1940–50: Sinatramania and decline of career
In the autumn of 1940, Sinatra appeared in his first film, Las Vegas Nights. In May 1941, Sinatra was at the top of the male singer polls in the Billboard and Downbeat 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 31, 1942, Sinatra opened at the Paramount Theater in New York. 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 didn’t 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 2, 1943.
In 1943, he signed with Columbia Records as a solo artist with initially great success, particularly during the musicians' recording strikes. Sinatra signed with Columbia on June 1, 1943, with the musicians' strike ten months old. And while 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 7, June 22, August 5, and November 10, 1943. Of the nine songs recorded during these sessions, seven charted on the best–selling list.
Sinatra went before his draft board on December 11, 1943, and received a 4-F "Registrant not acceptable for military service." classification for a perforated eardrum on his records.
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". G.I.'s in the service, like 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 deferment would resurface throughout his life and cause him grief when he had to defend himself. There would be accusations, including some from noted columnist Walter Winchell, that Sinatra paid $40,000 to avoid the service — but the FBI could find no evidence of this.
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.
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 himself 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 (following Billy Eckstine, Frankie Laine, and Bing Crosby).
The year 1949 saw an upswing, as Frank once again teamed up with Gene Kelly to co-star in Take Me Out to the Ball Game. It was well received critically and became a major commercial success. That same year, Sinatra would team up with Gene Kelly for a third time in On the Town.
1950–60: Rebirth of career, Capitol concept albums
After two years' absence, Sinatra returned to the concert stage on January 12, 1950, in Hartford, Connecticut. Sinatra's voice suffered and he experienced hemorrhaging of his vocal cords on stage at the Copacabana on April 26, 1950. Sinatra's career and appeal to new teen audiences declined as he moved into his mid-30s.
In September 1951, Sinatra made his Las Vegas debut at the Desert Inn. A month later, a second series of the Frank Sinatra Show aired on CBS. On November 7, 1951, Sinatra married Ava Gardner. They had an extremely tempestuous relationship, and the ascent of Gardner's career seemed to coincide with the decline in Sinatra's. They split up in 1953 and divorced in 1957.
Columbia and MCA dropped Sinatra 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 mark the turnaround in Sinatra's career, in which he went from being in a critical and commercial decline for several years to an Oscar-winning actor and, once again, one of the top recording artists in the world.
Also in 1953, Sinatra starred in the NBC radio program Rocky Fortune. His character, Rocko Fortunato (aka Rocky Fortune) was a private eye who was placed in a variety of odd jobs by the Gridley Employment Agency in order to help solve crimes. The series aired on NBC radio Tuesday nights from October 1953 to March 1954. 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, most notably Nelson Riddle, Gordon Jenkins, and Billy May. Sinatra reinvented himself with a series of albums featuring darker emotional material, starting with In the Wee Small Hours (1955), and followed by Frank Sinatra Sings For Only The Lonely (1958), and Where Are You? (1957). He also developed a hipper, "swinging" persona, as heard on Swing Easy! (1954), Songs For Swingin' Lovers (1956), Come Fly With Me (1957).
Also in 1955, Sinatra's first 12" LP In the Wee Small Hours, his second collaboration with Nelson Riddle, was released.
A third collaboration with Nelson Riddle, Songs For Swingin' Lovers, was a success, featuring a recording of "I've Got You Under My Skin."
Frank Sinatra Sings for Only the Lonely, a stark collection of introspective saloon songs and blues-tinged ballads, was a mammoth commercial success, peaking at #1 on Billboard's album chart during a 120-week stay. Cuts from this LP, such as "Angel Eyes" and "One for My Baby (and One More for the Road)," would remain staples of Sinatra's concerts throughout his life.
Throughout the fifties, Sinatra frequently criticized rock 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 sideburned delinquent on the face of the earth."
1960–70: Ring-A-Ding-Ding, Reprise records, Basie, Jobim, "My Way"
Sinatra would start the 1960s as he ended the 1950s, his first album of the decade, Nice 'n' Easy, topping Billboard's album chart and winning critical plaudits en masse, this, despite Sinatra growing discontented at Capitol Records and having 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 #4 on Billboard and #8 in the UK.
On January 27, 1961, Sinatra played a benefit show at Carnegie Hall for Martin Luther King, Jr. and would go on to play a major role in the desegregation of Nevada hotels and casinos in the 1960s. Sinatra led his fellow members of the Rat Pack and label-mates on Reprise in refusing to patronize hotels and casinos that wouldn't allow black singers to play live or wouldn't allow black patrons entry. He would often speak from the stage on desegregation. He would play more benefits for Martin Luther King, Jr. who, according to Frank Sinatra, Jr., at one point during a show in 1963 sat weeping as Sinatra sang Ol' Man River, the song from the musical Show Boat that, in the show, is sung by an African-American stevedore.
Over September 11 and 12, 1961, Sinatra recorded his final songs for Capitol Records.
In 1962, along with Janet Leigh and Laurence Harvey, he starred in the political thriller The Manchurian Candidate as Bennett Marco. That same year, Sinatra and Count Basie collaborated for the album Sinatra-Basie. This popular and successful release would prompt them to rejoin two years later for a follow-up It Might as Well Be Swing, which was arranged by Quincy Jones. One of Sinatra's more ambitious albums from the mid-1960s was The Concert Sinatra, which was recorded with a 73-piece symphony orchestra on 35 mm tape.
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 St. Louis to benefit Dismas House. The 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, with a career anthology A Man and His Music followed in November, itself 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.
In the spring, That's Life appeared, with both the single and album becoming Top Ten hits in the US on Billboard's pop charts. Strangers in the Night went on to top the Billboard and UK pop singles charts, winning the award for Record of the Year at the Grammys. The album of the same name also topped the Billboard chart and reached number 4 in the UK.
Sinatra would start 1967 with a series of recording sessions with Antonio Carlos Jobim. Later in the year, a duet with daughter Nancy, "Somethin' Stupid," topped the Billboard pop and UK singles charts. In December, Sinatra collaborated with Duke Ellington on the album Francis A. & Edward K.
During the late 1960s, press agent Lee Solters would invite columnists with their spouses into Sinatra's dressing room just before he was about to go on stage. The New Yorker recounted that "The first columnist they tried this on was Larry Fields of the Philadelphia Daily News, whose wife fainted when Sinatra kissed her cheek. 'Take care of it, Lee,' Sinatra said, and he was off."
Back on the small-screen, Sinatra once again worked with Antonio Carlos Jobim, with Ella Fitzgerald on the TV special A Man and His Music + Ella + Jobim.
Watertown (1970) was one of Sinatra's most acclaimed concept albums, but was all but ignored by the public in commercial terms. Selling a mere 30,000 copies, and reaching a peak chart position of 101, its failure put an end to plans of a television special based on the album.
With Sinatra in mind, singer-songwriter Paul Anka wrote the song "My Way" inspired from the French "Comme d'habitude" ("As Usual"), composed by Claude François and Jacques Revaux. "My Way" would, perhaps, become more identified with him than any other over his seven decades as a singer.
1970–80: Retirement and comeback
On June 12, 1971 — at a concert in Hollywood to raise money for the Motion Picture and TV Relief Fund — at the age of 55, Sinatra announced that he was retiring, bringing to an end his 36-year career in show business.
In 1973, Sinatra came out of retirement with a television special and album, both entitled Ol' Blue Eyes Is Back. The album, arranged by Gordon Jenkins and Don Costa, was a great success, reaching number 13 on Billboard and number 12 in the UK. The TV special was highlighted by a dramatic reading of "Send in the Clowns" and a song and dance sequence with former co-star Gene Kelly.
In January 1974, Sinatra returned to Las Vegas, performing at Caesars Palace despite vowing in 1970 never to play there again after the manager of the resort, Sanford Waterman, pulled a gun on him during a heated argument. With Waterman recently shot, the door was open for Sinatra to return.
In Australia, he caused an uproar by describing journalists there — who were aggressively pursuing his every move and pushing for a press conference — as "fags," "pimps," and "whores." Australian unions representing transport workers, waiters, and journalists went on strike, demanding that Sinatra apologize for his remarks. Sinatra instead insisted that the journalists apologize for "fifteen years of abuse I have taken from the world press." The future Prime Minister of Australia, Bob Hawke, then the Australian Council of Trade Unions (ACTU) leader, also insisted that Sinatra apologize, and a settlement was eventually reached to the apparent satisfaction of both parties, Sinatra's final show of his Australian tour was televised to the nation.
In October 1974, Sinatra appeared at New York City's Madison Square Garden in a televised concert that was later released as an album under the title The Main Event – Live. Backing him was bandleader Woody Herman and the Young Thundering Herd, who accompanied Sinatra on a European tour later that month. The TV special garnered mostly positive reviews whilst the album — actually culled from various shows during his comeback tour — was only a moderate success, peaking at #37 on Billboard and #30 in the UK.
In 1979, in front of the Egyptian pyramids, Sinatra performed for Anwar Sadat. Back in Las Vegas, while celebrating 40 years in show business and his 64th birthday, he was awarded the Grammy Trustees Award during a party at Caesars Palace.
1980–90: Trilogy, She Shot Me Down, L.A. Is My Lady
Sinatra sings with then First Lady Nancy Reagan at the White House. In 1980, Sinatra's first album in six years was released, Trilogy: Past Present Future, a highly ambitious triple album that found Sinatra recording songs from the past (pre-rock era) and present (rock era and contemporary) that he had overlooked during his career, while 'The Future' was a free-form suite of new songs linked à la musical theater by a theme, in this case, Sinatra pondering over the future. The album garnered six Grammy nominations — winning for best liner notes — and peaked at number 17 on Billboard's album chart, while spawning yet another song that would become a signature tune, "Theme from New York, New York" as well as Sinatra's much lauded (second) recording of George Harrison's "Something" (the first was not officially released on an album until 1972's Frank Sinatra's Greatest Hits Vol. 2.)
The following year, Sinatra built on the success of Trilogy with She Shot Me Down, an album that revisited the dark tone of his Capitol years, and was praised by critics as a vintage late-period Sinatra. Sinatra would comment that it was "A complete saloon album... tear-jerkers and cry-in-your-beer kind of things."
Sinatra was embroiled in controversy in 1981 when he worked a ten-day engagement for $2 million in Sun City, South Africa.
Frank Sinatra was selected as one of the five recipients of the 1983 Kennedy Center Honors, alongside Katharine Dunham, James Stewart, Elia Kazan and Virgil Thomson. Quoting Henry James in honoring Sinatra, Reagan said that "art was the shadow of humanity," and said that Sinatra had "spent his life casting a magnificent and powerful shadow."
Earlier that year, Sinatra had worked with Quincy Jones for the first time in nearly two decades on the album L.A. Is My Lady. Well received critically, L.A. Is My Lady came after an album of duets with Lena Horne, instigated by Jones, was abandoned after Horne developed vocal problems and Sinatra committed to other engagements, could not wait to record.
1990s: Duets, final performances
In 1990, Sinatra celebrated his 75th birthday with a national tour, and was awarded the second "Ella Award" by the Los Angeles–based Society of Singers. At the award ceremony, he performed for the final time with Ella Fitzgerald.
In December, as part of Sinatra's birthday celebrations, Patrick Pasculli, the Mayor of Hoboken, New Jersey, made a proclamation in his honor, declaring that "no other vocalist in history has sung, swung and crooned and serenaded into the hearts of the young and old... as this consummate artist from Hoboken". The same month Sinatra gave the first show of his Diamond Jubilee Tour at the Meadowlands Arena in East Rutherford, New Jersey.
In 1993 Sinatra made a surprise return to Capitol Records and the recording studio for Duets, which was released in November.
The artists who added their vocals to the album worked for free, and a follow-up album (Duets II) was released in 1994, which reached #9 on the Billboard charts.
Still touring, despite various health problems, Sinatra remained a top concert attraction on a global scale during the first half of the 1990s. At times, his memory seemed to fail him, and a fall onstage in Richmond, Virginia in 1994 signaled further problems.
Sinatra's final public concerts were held in Japan's Fukuoka Dome in December 1994. The following year, on February 25, 1995, at a private party for 1,200 select guests on the closing night of the Frank Sinatra Desert Classic golf tournament, Sinatra sang before a live audience for the very last time. Esquire reported of the show that Sinatra was "clear, tough, on the money" and "in absolute control." His closing song was "The Best is Yet to Come."
Sinatra was awarded the Legend Award at the 1994 Grammy Awards. He was introduced by Bono, who said of Sinatra "Frank's the chairman of the bad attitude... rock 'n roll plays at being tough, but this guy is the boss. The chairman of boss... I'm not going to mess with him, are you?" Sinatra called it "the best welcome...I ever had." However, during his speech, Sinatra apparently ran too long and was curtly cut off by music, then commercials, leaving Sinatra looking confused while talking into a dead microphone.
In 1995, to mark Sinatra's 80th birthday, the Empire State Building glowed blue. A star-studded birthday tribute, Sinatra: 80 Years My Way held at the Shrine Auditorium in Los Angeles, was his last televised appearance.
Sinatra was elected to the Gaming Hall of Fame in 1997.
Sinatra had three children; Nancy, Frank Jr. and Tina by his first wife Nancy Barbato (married 1939-1951). He was married three more times, to the actresses Ava Gardner (married 1951-1957) and Mia Farrow (married 1966-1968) and finally to Barbara Marx (married 1976), to whom he was still married at his death.
Throughout his life, Sinatra had mood swings and bouts of depression, symptoms of bipolar disorder, formerly known as manic depression. He himself acknowledged this fact, telling an interviewer in the 1950s: "Being an 18-karat manic-depressive, and having lived a life of violent emotional contradictions, I have an over-acute capacity for sadness as well as emotion."
In her memoirs My Father's Daughter, his daughter Tina wrote about the "eighteen-karat" remark: "As flippant as Dad could be about his mental state, I believe that a Zoloft a day might have kept his demons away. But that kind of medicine was decades off."
After suffering another heart attack, Frank Sinatra died at 10:50 pm on May 14, 1998 at the Cedars-Sinai Medical Center, with his wife Barbara by his side. He was 82 years old. Sinatra's final words, spoken as attempts were made to stabilize him, were "I'm losing it." 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 in his honor. President Bill Clinton led tributes to Sinatra, stating that he had managed "to appreciate on a personal level what millions of people had appreciated from afar." Elton John stated that Sinatra, "was simply the best - no one else even comes close."
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 at the border of Cathedral City and Rancho Mirage, near his famous Rancho Mirage compound, located on tree-lined Frank Sinatra Drive. His close friends Jilly Rizzo and Jimmy Van Heusen are buried nearby in the same cemetery.
The words "The Best Is Yet to Come" are imprinted on Sinatra's grave marker.
For a year Hoover investigated Sinatra's alleged communist affiliations, but came up empty-handed. Readers learn that the budding star, to get an exemption from military service, told draft-board doctors that he had an irrational fear of crowds. In truth he was drafted into the Army during World War II but got a 4F because of a damaged eardrum, something that was apparent at birth after a complicated delivery using forceps. 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.
Sinatra held differing political views throughout his life.
Sinatra's parents had immigrated to the United States in 1895 and 1897 respectively. His mother, Dolly Sinatra (1896-1977), was a Democratic Party ward boss.
Sinatra, pictured here with Eleanor Roosevelt in 1960, was an ardent supporter of the Democratic Party until 1968.Sinatra remained a supporter of the Democratic Party until the late 1960s when he switched his allegiance to the Republican Party.
Political activities 1944-1968
In 1944 after sending a letter to President Franklin D. Roosevelt, Sinatra was invited to meet Roosevelt at the White House, where he agreed to become part of the Democratic party's voter registration drives.
He donated $5,000 to the Democrats for the 1944 presidential election, and by the end of the campaign was appearing at two or three political events every day.
After World War II, Sinatra's politics grew steadily more left wing, and he became more publicly associated with the Popular Front. He started reading liberal literature, and supported many organizations that were later identified as front organizations of the Communist Party USA by the House Un-American Activities Committee in the 1950s, though Sinatra was never brought before the Committee.
Sinatra spoke at a number of New Jersey high schools in 1945, where students had gone on strike in opposition to racial integration. Later that year Sinatra would appear in The House I Live In, a short film that stood against racism. The film was scripted by Albert Maltz, with the title song written by Earl Robinson and Abel Meeropol (under the pseudonym of Lewis Allen).
In 1948, Sinatra supported the candidacy of Henry A. Wallace.
In January, 1961, Sinatra and Peter Lawford organized the Inaugural Gala in Washington, D.C., held on the evening before new President John F. Kennedy was sworn into office. The event, featuring many big show business stars, was an enormous success, raising a large amount of money for the Democratic Party. Sinatra also organized an Inaugural Gala in California in 1962 to welcome second term Democratic Governor Pat Brown.
Sinatra's move towards the Republicans seems to have begun when he was snubbed by President Kennedy in favor of Bing Crosby, a rival singer and a Republican, for Kennedy's visit to Palm Springs in 1962. Kennedy had planned to stay at Sinatra's home over the Easter holiday weekend, but decided against doing so because of problems with Sinatra's alleged connections to organized crime. Sinatra had invested a lot of his own money in upgrading the facilities at his home, in anticipation of the president's visit. President Kennedy's brother, Attorney General Robert F. Kennedy, was intensifying his own investigations into organized crime figures at the time, such as Chicago mob boss Sam Giancana, who had earlier stayed at Sinatra's home. The President and Giancana were also sharing the favors of mistress Judith Campbell, who was in frequent contact with the president. Giancana's under-the-table influence had been critical in capturing Illinois for the Democrats in the presidential election of 1960.
Political activities 1970-1984
On February 27, 1970 Sinatra sang at the White House as part of a tribute to Senator Everett Dirksen. Over the summer Sinatra supported another Republican candidate as he declared for Ronald Reagan in his race for a second term as the Governorship of California. Sinatra was also good friends with Vice President Spiro Agnew. Sinatra said he agreed with the Republican Party on most positions, except that of abortion.
After a lifetime of supporting Democratic presidential candidates, Sinatra supported Richard Nixon for re-election in the 1972 presidential election. In 1973, Spiro Agnew resigned the vice presidency, amid charges of bribery, extortion and tax fraud; Sinatra helped Agnew pay some of his legal bills that he faced after his exit from office.
Sinatra is awarded the Presidential Medal of Freedom by President Ronald Reagan.In the 1980 presidential election, Sinatra supported Ronald Reagan, and donated $4 million to Reagan's campaign. Sinatra said he supported Reagan as he was “the proper man to be the President of the United States… it's so screwed up now, we need someone to straighten it out”. Reagan's victory gave Sinatra his closest relationship with the White House since the early 1960s, as a result of which Sinatra arranged Reagan's Presidential gala, as he had done for John F. Kennedy, 20 years previously.
In 1984 Sinatra returned to his birthplace in Hoboken, New Jersey, bringing with him President Reagan, who was in the midst of campaigning for the 1984 presidential election. Reagan had made Sinatra a fund-raising ambassador as part of the Republicans' 'Victory 84’ get-the-vote-out-drive.