Francis Albert Sinatra, known universally as Frank Sinatra, was an American singer and actor whose career spanned over six decades, leaving an indelible mark on the entertainment landscape of the 20th century. He was born on December 12, 1915, in Hoboken, New Jersey, and passed away on May 14, 1998, in Los Angeles, California. Affectionately nicknamed "The Chairman of the Board" and famously known for his piercing "Ol' Blue Eyes," Sinatra is widely regarded as one of the most popular and influential entertainers of his era. His enduring legacy is cemented by his status as one of the world's best-selling music artists, with estimated global record sales exceeding 150 million.
Born to Italian immigrants, Antonino Martino "Marty" Sinatra and Natalina "Dolly" Garaventa, Sinatra's early life in Hoboken was marked by the challenges of an immigrant family. His father was from Sicily, and his mother hailed from Genoa. The sheer size of Sinatra at birth, a remarkable 13.5 pounds (6.1 kg), necessitated a difficult delivery with forceps, resulting in scarring on his left cheek, neck, and left ear, and causing lifelong damage to his eardrum. His grandmother, in a desperate attempt to revive him, ran him under cold water until he gasped, a harrowing event that delayed his baptism. The scars from this difficult birth, compounded by adolescent cystic acne, contributed to a certain ruggedness in his appearance, though this would later be softened by his undeniable charisma. Raised in the Catholic Church, Sinatra's upbringing was deeply influenced by his formidable mother, Dolly. She was a driving force in his life, credited by biographers with instilling in him the strong sense of self-confidence and will that would define his career. Dolly's influence extended beyond the home; she became a prominent figure in Hoboken's Democratic Party circles, even working as a midwife, and, according to biographer Kitty Kelley, allegedly ran an illegal abortion service, earning her the moniker "Hatpin Dolly."
His father, Marty, who was illiterate, worked his way up to captain in the Hoboken Fire Department. Marty emphasized the importance of education, encouraging Frank to pursue a career in civil engineering at the Stevens Institute of Technology. Sinatra spent considerable time in his parents' tavern, doing homework and occasionally singing for spare change. During the Great Depression, his mother's financial support allowed him to maintain a stylish appearance, earning him the neighborhood description of the "best-dressed kid." Despite his later fame, Sinatra's slender childhood frame became a recurring subject of jokes.
Sinatra's musical inclinations emerged early, fueled by an admiration for big band jazz and idols like Bing Crosby. A ukulele received for his 15th birthday became an instrument for performing at family gatherings. While attending David E. Rue Jr. High School and later A. J. Demarest High School (now Hoboken High School), he began arranging bands for school dances. However, his academic career was cut short; he left high school after just 47 days, expelled for "general rowdiness." To appease his mother, he enrolled in Drake Business School but soon departed. He worked as a delivery boy for the Jersey Observer newspaper and later as a riveter at the Tietjen and Lang shipyard. His early performing days saw him singing for free at local social clubs and on radio stations like WAAT in Jersey City. In New York, he sang for his supper or for cigarettes, and recognized the need to refine his speech, taking elocution lessons from John Quinlan, who was among the first to notice his exceptional vocal range.
Music career
1935–1942: Hoboken Four, Harry James, and Tommy Dorsey
Sinatra's professional singing career began in his teenage years. He possessed an innate musicality, learning by ear rather than reading music, a skill that would serve him well throughout his career. His breakthrough came in 1935 when his mother persuaded the local singing group, the 3 Flashes, to accept him. As baritone Fred Tamburro recalled, Sinatra "hung around us like we were gods," and their acceptance was partly due to his owning a car, which allowed him to chauffeur the group. Sinatra's eagerness led them to audition for Major Bowes' Amateur Hour, where, as the "Hoboken Four," they secured a six-month contract for national performances. Sinatra quickly emerged as the lead singer, drawing considerable female attention, which reportedly caused jealousy among his bandmates. The group's popularity led to repeated appearances on the show, sometimes under humorous, invented names, a detail often recounted in Sinatra's stage patter.
In 1938, Sinatra found work as a singing waiter at "The Rustic Cabin" roadhouse in Englewood Cliffs, New Jersey, a venue connected to radio station WNEW. Performing live during the "Dance Parade" show, he felt this was his pivotal opportunity, confidently telling friends he would become untouchable. In March 1939, saxophonist Frank Mane facilitated Sinatra's first solo studio recording, "Our Love." This led to a crucial audition with bandleader Harry James. Impressed by Sinatra's performance at the Paramount Theatre, James signed him to a two-year contract in June 1939. Sinatra's first commercial record with James, "From the Bottom of My Heart," released in July, saw modest sales, as did subsequent releases with James. However, his vocal training allowed him to extend his range, developing a repertoire that included songs like "My Buddy" and "Willow Weep for Me."
Frustrated by his lack of significant success with Harry James, Sinatra was persuaded by his pianist and friend, Hank Sanicola, to remain with the band. Nevertheless, in November 1939, Sinatra left James to join the Tommy Dorsey band as lead singer, earning a higher salary and gaining more prominence. Dorsey, a significant father figure in Sinatra's life, greatly influenced his vocal techniques and perfectionism. Sinatra's admiration for Dorsey was so profound that he copied his mannerisms and even adopted his hobby of toy trains. He later stated, "The only two people I've ever been afraid of are my mother and Tommy Dorsey." While some accounts suggest rivalry with drummer Buddy Rich, others indicate a friendship, though professional jealousy did surface. Sinatra's support for Rich extended to helping him form his own band and providing financial assistance during difficult times.
During his first year with Dorsey, Sinatra recorded over 40 songs, achieving his first vocal hit with "Polka Dots and Moonbeams" in April 1940. Subsequent chart successes included "Say It" and "Imagination." His first top-10 hit, "I'll Never Smile Again," spent twelve weeks at the top of the charts. Other notable recordings with Dorsey for RCA Victor included "Our Love Affair" and "Stardust" in 1940, and a string of hits in 1941 and 1942.
Sinatra's growing ambition led him to push Dorsey for solo recording opportunities. In January 1942, Sinatra recorded "Night and Day" and other tracks with arranger and conductor Axel Stordahl. The resulting recordings, which he heard at the Hollywood Palladium, were a revelation, solidifying his belief in his solo potential. This marked a turning point, as Sinatra recognized the possibility of forging his own path.
1942–1945: Onset of Sinatramania and Role in World War II
By 1942, Sinatra was eager to leave the Dorsey band, driven by an intense desire to rival Bing Crosby's success. However, his contract with Dorsey, which stipulated that Dorsey would receive 43% of Sinatra's earnings, presented a significant hurdle. A legal settlement in August 1942 finally freed Sinatra from the contract, though Dorsey's parting words reportedly conveyed a sense of bitterness. Rumors circulated that mobster godfather Willie Moretti had coerced Dorsey into releasing Sinatra. Sinatra retained Stordahl as his personal arranger, offering him a substantial salary increase. The rift between Sinatra and Dorsey remained, with the two never reconciling.
Sinatra's popularity surged by May 1941, topping polls in Billboard and DownBeat magazines. His appeal to teenage girls, dubbed "bobby soxers", introduced a new demographic to popular music. This phenomenon, officially termed "Sinatramania," peaked with his legendary appearance at the Paramount Theatre in New York on December 30, 1942. As Jack Benny later remarked, the sheer volume of the crowd's reaction – "I thought the goddamned building was going to cave in" – was unprecedented for an artist he hadn't heard of. Sinatra's four-week engagement was extended due to overwhelming demand, solidifying his status and earning him nicknames like "Swoonatra" and "The Voice." His devoted fans, the "Sinatratics," formed numerous clubs, sent masses of fan mail, and engaged in ardent displays of adoration, such as attempting to steal his bow ties.
Sinatra's publicist, George Evans, expertly crafted his image as a vulnerable, hard-working Italian-American overcoming adversity. This narrative resonated deeply with his audience. The fervor surrounding Sinatra reached a fever pitch during his October 1944 return to the Paramount, where a riot ensued outside the venue as 35,000 fans were denied entry. The devotion of his bobby-soxer fans was so intense that they would write his song titles on their clothing and bribe hotel staff for a chance to touch his belongings.
Sinatra signed with Columbia Records in June 1943, during the 1942–44 musicians' strike. Columbia re-released his 1939 recording of "All or Nothing at All," which became a massive hit, reaching number 2 on the charts. His early success at Columbia was significant; he starred on the radio show Your Hit Parade and performed regularly on stage. His nightclub debut at New York's Riobamba and a subsequent concert at the Waldorf-Astoria New York cemented his popularity within New York's high society. By the end of 1943, he surpassed Bing Crosby in popularity polls.
Sinatra did not serve in the military during World War II. Classified as 4-F by his draft board due to a perforated eardrum, Army files later indicated a rejection for "psychiatric viewpoint" due to emotional instability, a detail kept private to avoid public scrutiny. Despite rumors of paying to avoid service, the FBI found no evidence. As the war neared its end, Sinatra entertained troops on successful USO tours, including a memorable encounter with the Pope in Rome. He frequently collaborated with The Andrews Sisters on radio and for the Armed Forces Radio Service (AFRS). His recordings during this period included "I Couldn't Sleep a Wink Last Night" and his rendition of Irving Berlin's "White Christmas."
1946–1952: Columbia years and career slump
Despite his extensive political activism in 1945 and 1946, Sinatra maintained a prolific schedule of radio shows, recordings, and films. By 1946, he was performing up to 45 times a week and earning substantial income. His first album, The Voice of Frank Sinatra, released in 1946, reached No. 1 on the Billboard chart. Critics praised his serious approach to the material, noting the "unusual depth of meaning" in his singing and the classically influenced arrangements. Sinatra was selling millions of records annually.
During his tenure at Columbia, Sinatra indulged his passion for conducting with the release of Frank Sinatra Conducts the Music of Alec Wilder, an album that appealed less to his young fan base. His second album, Songs by Sinatra, released in 1947, featured a similar mood and tempo, including songs like Irving Berlin's "How Deep is the Ocean?" and Harold Arlen's and Jerome Kern's "All The Things You Are." The single "Mam'selle," from the film The Razor's Edge, also charted, though it faced competition from multiple other artists. His collaboration with the Metronome All-Stars on "Sweet Lorraine" in December 1947, featuring prominent jazz musicians, was noted as a highlight of his Columbia period.
Christmas Songs by Sinatra, released in 1948, was followed by his role as a priest in The Miracle of the Bells. Amidst negative press regarding alleged Mafia connections, Sinatra announced he would donate his $100,000 salary to the Catholic Church.
By the end of 1948, Sinatra's popularity waned, slipping in polls. His 1949 album, Frankly Sentimental, received a critical panning. While "The Hucklebuck" reached the top ten, it was his last single for Columbia. His final albums for the label, Dedicated to You and Sing and Dance with Frank Sinatra, were released in 1950. The death of his publicist George Evans in January 1950, a key figure in his career, was a significant blow.
Sinatra's personal life also became a subject of public scrutiny with reports of his affair with Ava Gardner and the breakdown of his marriage to Nancy. A throat hemorrhage in April 1950 forced him to cancel performances, exacerbating his career decline. Facing financial difficulties after his divorce, Sinatra borrowed heavily from Columbia to cover back taxes. Rejected by Hollywood, he turned to Las Vegas, debuting at the Desert Inn in September 1951.
His declining popularity was evident in his concert performances, with small audiences at venues like the Paramount and half-filled houses in Las Vegas. By April 1952, he was performing at the Kauai County Fair. Sinatra's relationship with Columbia Records deteriorated, with A&R executive Mitch Miller famously stating that Sinatra records were "unmarketable." Despite the downturn, recordings like "If I Could Write a Book" in January 1952 showed a promising glimpse of his future artistic direction. Columbia and MCA ultimately dropped Sinatra in late 1952, marking a low point in his career. His final Columbia recording, "Why Try to Change Me Now," was made on September 17, 1952. Journalist Burt Boyar described the situation as Sinatra having "had it."
1953–1960: Career revival and the Capitol years
The release of the film From Here to Eternity in August 1953 heralded a remarkable resurgence in Sinatra's career. He embarked on a period of intense work, marked by a "frenetic schedule of recordings, movies and concerts." On March 13, 1953, Sinatra signed a seven-year contract with Capitol Records, initiating a period of immense creative and commercial success. His first Capitol session, with Axel Stordahl, produced the single "I'm Walking Behind You."
Following his Oscar-winning performance in From Here to Eternity, Sinatra's collaboration with arranger Nelson Riddle began on April 30, 1953. The recording of "I've Got the World on a String" elicited a rare expression of praise from Sinatra: "Beautiful!" He exclaimed, "I'm back, baby, I'm back!" This partnership proved exceptionally fruitful, with Sinatra and Riddle refining their musical approach through subsequent sessions. Sinatra's first Capitol album, Songs for Young Lovers, released in January 1954, included standards that became concert staples.
That same month, Sinatra released the single "Young at Heart," which reached No. 2 and was named Song of the Year. His March 1954 recording of "Three Coins in the Fountain" became another hit. Swing Easy!, his second album with Riddle, captured his affinity for jazz and was named Album of the Year by Billboard. Sinatra's accolades continued as he was named "Favorite Male Vocalist" by Billboard, DownBeat, and Metronome in 1954. He considered Riddle "the greatest arranger in the world," while Riddle praised Sinatra's impeccable taste and vocal intuition.
Sinatra became a fixture in Las Vegas, pioneering the residency format and becoming a prominent figure in the city's burgeoning entertainment scene throughout the 1950s and beyond. The Rat Pack, a group of entertainers including Dean Martin, Sammy Davis Jr., Peter Lawford, and Joey Bishop, provided a platform for camaraderie and performance. Sinatra's association with the Sands Hotel and Casino began in October 1953, and he eventually acquired a share in the establishment.
In 1955, Sinatra released In the Wee Small Hours, his first 12" LP, a concept album noted for its "melancholy mood." His first Australian tour also took place that year. The critically acclaimed Songs for Swingin' Lovers! followed in March 1956, featuring a rendition of Cole Porter's "I've Got You Under My Skin" that reportedly required 22 takes. His February 1956 recording sessions marked the inauguration of the Capitol Records Building studios, featuring a large orchestra. Sinatra's performances of songs like "Night and Day" and "The Lady is a Tramp" were noted for their "powerful sexual overtones" and vocal nuances. He also released Frank Sinatra Conducts Tone Poems of Color in 1956, an instrumental album interpreted as a reflection of his personal life.
The late 1950s saw Sinatra release a series of highly successful albums, including Close to You and A Swingin' Affair!, which solidified his "swinger" image. The concept album Come Fly with Me, released in 1958, topped the Billboard album chart for five weeks and was nominated for the Grammy Award for Album of the Year. Later that year, Frank Sinatra Sings for Only the Lonely, a collection of introspective ballads, also reached No. 1 and remained on the charts for 120 weeks. In 1959, Come Dance with Me! achieved critical acclaim and commercial success, winning the Grammy for Album of the Year. Sinatra's prolific output continued with No One Cares and Nice 'n' Easy, which topped the Billboard chart in October 1960.
1960–1970: Reprise years
Dissatisfied with Capitol Records, Sinatra sought greater creative control and established his own label, Reprise Records, in 1960. This move allowed him to collaborate with a range of arrangers, including Neil Hefti, Don Costa, and Quincy Jones. Reprise quickly became a major force in the music industry, with Sinatra eventually selling it for a significant sum. His first Reprise album, Ring-a-Ding-Ding! (1961), was a commercial success. During this period, Sinatra also completed his contractual obligations to Capitol with the release of Point of No Return.
Sinatra's collaborations with Count Basie resulted in the successful albums Sinatra-Basie (1962) and It Might as Well Be Swing (1964), solidifying their musical partnership. He also resumed his role as a conductor with Frank Sinatra Conducts Music from Pictures and Plays (1962). The reunion with Nelson Riddle for The Concert Sinatra (1963) featured a large orchestra and showcased Sinatra's vocal prowess, particularly on "Ol' Man River."
In 1965, Sinatra's 50th birthday coincided with a period of immense success, with Billboard declaring he had reached the "peak of his eminence." His album September of My Years won the Grammy for Best Album of the Year, and the single "It Was a Very Good Year" won Best Vocal Performance, Male. The anthology A Man and His Music earned the Album of the Year Grammy the following year. Sinatra's 1966 albums That's Life and Strangers in the Night were both Top Ten hits, with the latter winning Record of the Year. His first live album, Sinatra at the Sands, recorded in 1966, featured the Count Basie Orchestra.
The late 1960s saw Sinatra explore new musical territories, collaborating with Antônio Carlos Jobim on the Grammy-nominated album Francis Albert Sinatra & Antônio Carlos Jobim, which achieved significant commercial success. His album The World We Knew included the chart-topping duet "Somethin' Stupid" with his daughter Nancy. He also collaborated with Duke Ellington on Francis A. & Edward K.. In 1969, Sinatra recorded "My Way," a song that would become one of his signature tunes, though its initial chart performance was modest. He also embraced contemporary music, recording works by Paul Simon, the Beatles, and Joni Mitchell in 1969.
1970–1981: "Retirement" and return
Sinatra's 1970 concept album Watertown received critical acclaim but had limited commercial success. He departed Caesars Palace in September 1970 after an incident involving a gun. After performing charity concerts with Count Basie in London, Sinatra recorded his final songs for Reprise Records before announcing his retirement in June 1971. His farewell performance, a benefit for the Motion Picture and TV Relief Fund, concluded with him singing "'Scuse me while I disappear."
During his brief retirement, Sinatra focused on personal projects, including designing his desert retreat, Villa Maggio. He returned to the public eye in 1973 with the television special and album Ol' Blue Eyes Is Back, which marked a successful comeback. Despite initial vocal challenges due to the hiatus, Sinatra embarked on a major international tour. However, a controversial incident in Australia in July 1974, where he made derogatory remarks about journalists, led to concert cancellations and a grounding of his plane. Sinatra eventually issued a conciliatory note and performed a televised concert at Madison Square Garden, released as The Main Event—Live.
In 1975, Sinatra continued his extensive touring, performing with notable artists like Count Basie, Ella Fitzgerald, and Sarah Vaughan. He also collaborated with John Denver, recording some of his songs. Sinatra played a pivotal role in reuniting Dean Martin and Jerry Lewis for the "Jerry Lewis MDA Telethon" in 1976. That year, he was honored by the Friars Club as the "Top Box Office Name of the Century."
The death of his mother, Dolly, in a plane crash in 1977 deeply affected Sinatra, leading him to cancel performances and seek solace in Barbados. He continued to record and perform, including a final session with Nelson Riddle in March 1977, though their partnership later dissolved before being mended. In 1979, Sinatra celebrated 40 years in show business and received the Grammy Trustees Award.
The 1980s saw Sinatra release the ambitious triple album Trilogy: Past Present Future, which included the signature song "Theme from New York, New York." He also broke attendance records with a concert in Rio de Janeiro's Maracanã Stadium. His 1981 album She Shot Me Down was praised for its dark tone, reminiscent of his Capitol years. However, his engagement in Sun City in South Africa, breaking a cultural boycott, drew controversy.
1982–1997: Later career and final projects
By the early 1980s, Sinatra's voice had matured, becoming "darker, tougher and loamier," though his ability to captivate audiences remained undiminished. He signed a lucrative deal with the Golden Nugget Las Vegas in 1982. Sinatra was honored at the 1983 Kennedy Center Honors, with President Reagan describing him as casting "a magnificent and powerful shadow." His legal battle with biographer Kitty Kelley over her unauthorized biography highlighted Sinatra's desire to control his own narrative.
In 1984, Sinatra collaborated with Quincy Jones for the album L.A. Is My Lady. A stage collapse in Atlantic City in 1986 led to hospitalization for diverticulitis, leaving him visibly frail. The subsequent Rat Pack Reunion Tour with Martin and Davis ended with a rift between Sinatra and Martin. Sinatra's last recordings for Reprise were made in 1988, but the project remained unreleased.
In the early 1990s, Sinatra maintained an active touring schedule. In 1993, he returned to Capitol Records for Duets, which became his best-selling album, followed by Duets II. Despite occasional memory lapses and a stage fainting incident in 1994, Sinatra continued to perform. His final public concerts were in Japan in December 1994, and his last performance was in February 1995. He received the Grammy Legend Award in 1994 and was celebrated with a star-studded tribute for his 80th birthday. Sinatra was inducted into the Gaming Hall of Fame in 1997.
Artistry
Sinatra's artistry was characterized by his innate musical understanding, despite not being a proficient reader of music. He possessed a "sixth sense" for detecting incorrect notes and sounds within an orchestra, a talent noted by classically trained musicians. His appreciation for classical music, particularly composers like Puccini and Ralph Vaughan Williams, influenced his own musical preferences. Sinatra insisted on recording live with bands, seeking the visceral connection it provided. His ability to interpret lyrics with profound emotional depth was a hallmark of his performances.
Vocal coach John Quinlan recognized Sinatra's impressive range, noting his ability to sing in full voice up to a high B-flat without amplification. Early influences included Bing Crosby, but Sinatra later expressed admiration for Tony Bennett, who described Sinatra as having "perfected the art of intimacy." Arranger Nelson Riddle observed Sinatra's "fairly rangy voice" with its distinct registers and "infinite taste, with an overall inflection of sex." Despite a noticeable New Jersey accent, Sinatra's diction became precise and meticulous when singing. His impeccable timing allowed him to "toy with the rhythm of a melody," creating a captivating performance. Tommy Dorsey noted Sinatra's ability to sustain musical phrases, a technique likely influenced by Dorsey's own exceptional breath control. Sinatra's dedication to improving his breathing power included regular swimming and breath-holding exercises.
Sinatra was a notorious perfectionist, often driving himself and his collaborators to exacting standards. His unpredictable temperament could create an atmosphere of unease for those working with him. His obsession with perfection occasionally led to postponed recording sessions, even if musicians were paid for their time. Sinatra actively sought out talented new songwriters, recording extensively the works of Sammy Cahn and later Jimmy Van Heusen. He insisted on direct input into arrangements and tempos, meticulously planning his recording sessions. Barbara Sinatra noted his habit of crediting songwriters and sharing his delight in the music with the audience.
Nelson Riddle observed that Sinatra's voice developed a greater "interest" over time, acquiring distinct colors and ranges that allowed for deeper emotional exploration of songs. The breakup of his relationship with Ava Gardner in 1953 profoundly impacted his singing, leading to more introspective and melancholic performances. Author Charles L. Granata considered Sinatra a "master of the art of recording," whose studio work set him apart. Throughout his career, he made over 1,000 recordings, typically in three-hour sessions that followed extensive preparation. Sinatra's choice of microphones evolved, from the RCA Type 44 during his Columbia years to the Neumann U 47 at Capitol, which better captured his vocal timbre. Technological advancements in the 1950s, such as the 12-inch LP, allowed Sinatra to craft "concept albums," where each track contributed to a larger thematic statement, redefining the nature of pop vocal artistry.
Film career
Sinatra harbored ambitions for an acting career from the early 1940s, though he was often critical of his own performances, famously stating, "pictures stink." His film debut was an uncredited appearance in Las Vegas Nights (1941), singing with Tommy Dorsey's orchestra. He had brief cameos in Reveille with Beverly (1943) and later secured leading roles in Higher and Higher and Step Lively.
His collaboration with Gene Kelly in the Technicolor musical Anchors Aweigh (1945) was a significant success, garnering Academy Award nominations and featuring the Oscar-nominated song "I Fall in Love Too Easily." Sinatra reunited with Kelly for Take Me Out to the Ball Game (1949) and the critically acclaimed On the Town (1949), which remains highly regarded among musical films. However, films like Double Dynamite (1951) and Meet Danny Wilson (1952) failed to make a substantial impact.
1953–1959: Career comeback and prime
Sinatra's career received a critical boost with his performance as Angelo Maggio in Fred Zinnemann's From Here to Eternity (1953). Desperate for a significant role, Sinatra secured the part after numerous appeals to Columbia Pictures head Harry Cohn. His portrayal earned him the Academy Award for Best Supporting Actor and a Golden Globe Award. The Los Angeles Examiner lauded his performance as "simply superb, comical, pitiful, childishly brave, pathetically defiant."
He starred opposite Doris Day in the musical Young at Heart (1954) and received critical praise for his role as a psychopathic killer in the film noir Suddenly (1954). Sinatra's performance as a heroin addict in The Man with the Golden Arm (1955) earned him an Academy Award nomination and a BAFTA Award nomination. He followed this with roles in Guys and Dolls and The Tender Trap (both 1955). His portrayal of a medical student in Not as a Stranger (1955) also garnered a BAFTA nomination.
Sinatra starred alongside Bing Crosby and Grace Kelly in the successful musical High Society, a box office hit. He earned a Golden Globe Award for Best Actor – Motion Picture Musical or Comedy for his role as a comedian in Pal Joey (1957), with his rendition of "The Lady Is a Tramp" considered a career highlight. He portrayed comedian Joe E. Lewis in The Joker Is Wild (1957), which featured the Oscar-winning song "All the Way." By 1958, Sinatra was among the top ten box office draws in the United States, appearing in films like Some Came Running and Kings Go Forth. His performance in the 1959 film A Hole in the Head included the Oscar-winning song "High Hopes."
1960–1980: Later career
Sinatra starred in Can-Can (1960) and the iconic Las Vegas-set Ocean's 11 (1960), which launched the Rat Pack's film careers. He considered his role in The Manchurian Candidate (1962) to be the most exciting of his career and a professional high point. He also appeared with the Rat Pack in Sergeants 3 (1962) and Robin and the 7 Hoods (1964). His performance in Come Blow Your Horn (1963) earned him a Golden Globe nomination.
Sinatra directed only one film, the anti-war drama None but the Brave (1965), in which he also starred. He achieved further success with Von Ryan's Express (1965). In the late 1960s, he frequently portrayed detectives in films such as Tony Rome (1967) and The Detective. Although he turned down the role of John McClane in Die Hard due to his age, his earlier role in The Detective was based on the novel sequel. His last major film role was in The First Deadly Sin (1980), where his portrayal of a homicide cop was described as "extraordinarily rich" and a fitting farewell to his film career. Sinatra was also considered for the role of Harry Callahan in Dirty Harry (1971) but had to decline due to a hand condition.
Television and radio career
Sinatra's presence on radio began in 1935 with the Major Bowes Amateur Hour and continued through the 1940s and 1950s with his own shows on NBC and CBS. He hired Axel Stordahl as his arranger for radio work, and by late 1942, he was recognized as the "Most Popular Male Vocalist on Radio." He frequently appeared with The Andrews Sisters on radio and USO broadcasts. Sinatra had two stints on Your Hit Parade, from 1943–1945 and again from 1946–1949. His radio show "Light Up Time" for Lucky Strike ran from 1949 to 1950.
While Sinatra starred in his own television shows, including The Frank Sinatra Show and later The Frank Sinatra Show, he never felt entirely at ease in the medium. A significant moment was his 1960 TV special, Welcome Home Elvis, where he performed a duet with Elvis Presley, a notable shift after his earlier criticism of rock and roll. The Emmy and Peabody Award-winning television special Frank Sinatra: A Man and His Music (1965) cemented his television presence. He also appeared in specials with Antônio Carlos Jobim and Ella Fitzgerald. Post-retirement, he starred in the TV special Ol' Blue Eyes Is Back (1973). Sinatra's sole starring role in a dramatic television film was Contract on Cherry Street (1977). He made a guest appearance on Magnum, P.I. in 1987.
Personal life
Sinatra was married four times. His first marriage was to Nancy Barbato, from 1939 to 1951, with whom he had three children: Nancy (born 1940), Frank Jr. (1944–2016), and Tina (born 1948). Sinatra met Barbato in 1934, and their marriage was reportedly influenced by a pregnancy. Throughout his marriage to Nancy, Sinatra had numerous extramarital affairs.
His turbulent marriage to actress Ava Gardner lasted from 1951 to 1957, marked by public disputes but also a lifelong friendship. Sinatra later married actress Mia Farrow in 1966, divorcing in 1968; they also remained close friends. Farrow's suggestion in 2013 that Sinatra might be Ronan Farrow's biological father was dismissed by Nancy Sinatra, who stated their father had a vasectomy. Sinatra's final marriage was to Barbara Marx from 1976 until his death.
Sinatra maintained close friendships with numerous figures, including Jilly Rizzo, Jimmy Van Heusen, and President John F. Kennedy. He enjoyed classical music, swam daily, and pursued hobbies such as painting and building model railways. Despite periods of questioning his faith, Sinatra returned to Catholicism later in life and received a Catholic burial.
Style and personality
Sinatra was renowned for his impeccable style, favoring custom-tailored suits that made him feel confident and presentable for his audience. He was also meticulous about cleanliness, earning the nickname "Lady Macbeth" for his frequent showering and wardrobe changes. His deep blue eyes led to the nickname "Ol' Blue Eyes."
Described as the embodiment of 1950s American optimism, Sinatra exuded charisma and a sense of possibility. His friend Cary Grant called him "the most honest person" he had ever met. Sinatra was a workaholic, often sleeping only four hours a night. He experienced significant mood swings and bouts of depression, admitting to an "over-acute capacity for sadness as well as elation." His temper could be volatile, leading to confrontations with journalists and photographers.
Sinatra's temper also manifested in physical altercations, with incidents reported involving journalists and publicists. His feuds with columnists like Mike Royko and his verbal assaults on journalists highlighted his confrontational nature. Despite these outbursts, Sinatra was also known for his generosity, particularly after his career revival, offering significant support to friends and charitable causes.
Alleged organized-crime links and Cal Neva Lodge
Sinatra's working-class Italian-American background and embrace of a "tough" persona led to frequent speculation about his ties to organized crime. His godfather, Willie Moretti, an underboss of the Genovese crime family, reportedly assisted Sinatra, including in his contract dispute with Tommy Dorsey. Sinatra's presence at the Havana Conference in 1946 alongside Lucky Luciano fueled negative press. He was also reportedly acquainted with mobsters like Sam Giancana and Bugsy Siegel. The FBI maintained extensive files on Sinatra, tracking his alleged connections and political activities. His closeness to President Kennedy, however, reportedly led to friction with the Mafia, as Attorney General Robert F. Kennedy intensified efforts against organized crime. Sinatra consistently denied any involvement with criminal elements.
In 1960, Sinatra invested in the Cal Neva Lodge & Casino in Lake Tahoe, attracting numerous show business friends. His gambling license was temporarily suspended in 1963 due to Giancana's presence at the lodge. Under pressure from federal authorities, Sinatra relinquished his shares in the Cal Neva and the Sands. His son, Frank Jr., was famously kidnapped in 1963 but returned unharmed.
Political views and activism
Sinatra's political affiliations evolved throughout his life. Raised in a Democratic household, he actively campaigned for Democratic candidates, including Presidents Franklin D. Roosevelt, Harry S. Truman, and Adlai Stevenson. He was an outspoken critic of racism and played a role in the desegregation of musicians' unions. His association with President John F. Kennedy was particularly close, though security concerns related to Sinatra's alleged Mafia ties led Kennedy to distance himself. The snub by Kennedy, who chose to stay with Bing Crosby during a visit to Palm Springs, reportedly devastated Sinatra.
Later in his career, Sinatra shifted his political allegiance, endorsing Republican Ronald Reagan and supporting Richard Nixon in the 1972 presidential election. He donated significantly to Reagan's campaigns and arranged presidential galas. In 1985, Reagan presented Sinatra with the Presidential Medal of Freedom.
Sinatra was a lifelong supporter of Jewish causes, performing benefit concerts in Israel and donating fees to youth centers. He also demonstrated consistent sympathy for Black Americans, working to advance civil rights and playing a role in the desegregation of Nevada casinos. He organized a benefit concert for Martin Luther King Jr. and encouraged boycotts of establishments that denied entry to Black patrons. However, his political shift in the 1970s saw him become less vocal on racial issues.
Death and funeral
In his final years, Sinatra suffered from declining health, including heart and breathing problems, high blood pressure, and pneumonia. He made no public appearances after a heart attack in February 1997. Sinatra died peacefully in his sleep on May 14, 1998, at the age of 82, following another heart attack. The night after his death, tributes poured in, with landmarks like the Empire State Building and the Las Vegas Strip lights dimmed in his honor.
Sinatra's funeral was held on May 20, 1998, at the Church of the Good Shepherd in Beverly Hills, California. He was buried in a blue suit, with his grave marked by the epitaphs "The Best Is Yet to Come" and "Beloved Husband & Father." The marker was later updated to "Sleep Warm, Poppa" due to damage.
Legacy and honors
Frank Sinatra's legacy is immense, with critics hailing him as "the greatest singer of the 20th century." His popularity rivaled that of Elvis Presley and the Beatles. He is remembered as the "greatest male pop singer in the history of America," embodying the "common man" who achieved extraordinary success while remaining connected to his roots. Sinatra's charisma, vocal genius, and showmanship made him an icon of the 20th century, with three stars on the Hollywood Walk of Fame.
His hometown of Hoboken honored him with the Key to the City and rededicated its main post office in his name. Landmarks, streets, and institutions bear his name, including Frank Sinatra Park and the Frank Sinatra School of the Arts. Sinatra received numerous awards and honors throughout his career, including 11 Grammy Awards, an Academy Award, and the Presidential Medal of Freedom. The United States Postal Service issued a stamp in his honor in 2008, and May 13 was designated Frank Sinatra Day by Congress. Sinatra's influence continues to resonate, with tribute albums, films, and ongoing recognition of his unparalleled contribution to music and entertainment.