Life of Frank Sinatra Part I

 

Francis Albert Sinatra (/sɪˈnɑːtrə/; December 12, 1915 – May 14, 1998) was an American singer and actor. Nicknamed the "Chairman of the Board" and later called "Ol' Blue Eyes", he is regarded as one of the most popular entertainers of the mid-20th century. Sinatra is among the world's best-selling music artists with an estimated 150 million record sales.

Born to Italian immigrants in Hoboken, New Jersey, Sinatra began his musical career in the swing era and was greatly influenced by the easy-listening vocal style of Bing Crosby. He found success as a solo artist after signing with Columbia Records in 1943, becoming the idol of the "bobby soxers". In 1946, Sinatra released his debut album, The Voice of Frank Sinatra. He then signed with Capitol Records and released several critically lauded albums. In 1960, Sinatra left Capitol Records to start his own record label, Reprise Records, releasing a string of successful albums. In 1965, he recorded the retrospective album September of My Years and starred in the Emmy-winning television special Frank Sinatra: A Man and His Music. After releasing Sinatra at the Sands in early 1966, Sinatra recorded one of his most famous collaborations with Tom Jobim, the album Francis Albert Sinatra & Antonio Carlos Jobim. It was followed by 1968's Francis A. & Edward K. with Duke Ellington. Sinatra retired in 1971 following the release of "My Way", but came out of retirement two years later. He recorded several albums and released "New York, New York" in 1980.

Sinatra forged a highly successful career as a film actor. After winning the Academy Award for Best Supporting Actor for From Here to Eternity (1953), he starred in The Man with the Golden Arm (1955) and The Manchurian Candidate (1962). Sinatra also appeared in musicals such as On the Town (1949), Guys and Dolls (1955), High Society (1956), and Pal Joey (1957), which won him a Golden Globe Award. Toward the end of his career, he frequently played detectives, including the title character in Tony Rome (1967). Sinatra received the Golden Globe Cecil B. DeMille Award in 1971. On television, The Frank Sinatra Show began on CBS in 1950, and he continued to make appearances on television throughout the 1950s and 1960s.

In 1983, Sinatra was honored at the Kennedy Center Honors. He was awarded the Presidential Medal of Freedom in 1985 and the Congressional Gold Medal in 1997. Sinatra received eleven Grammy Awards including the Grammy Trustees Award, Grammy Legend Award, and the Grammy Lifetime Achievement Award. He was included in Time magazine's compilation of the 20th century's 100 most influential people. American music critic Robert Christgau called him "the greatest singer of the 20th century" and he continues to be regarded as an iconic figure.

Early life

"They'd fought through his childhood and continued to do so until her dying day. But I believe that to counter her steel will he'd developed his own. To prove her wrong when she belittled his choice of career ... Their friction first had shaped him; that, I think, had remained to the end and a litmus test of the grit in his bones. It helped keep him at the top of his game."—Sinatra's daughter Nancy on the importance of his mother Dolly in his life and character.

Francis Albert Sinatra was born on December 12, 1915, in a tenement at 415 Monroe Street in Hoboken, New Jersey, the only child of Italian immigrants Natalina "Dolly" Garaventa and Antonino Martino "Marty" Sinatra, who boxed under the name Marty O'Brien. Sinatra weighed 13.5 pounds (6.1 kg) at birth and had to be delivered with the aid of forceps, which caused severe scarring to his left cheek, neck, and ear, and perforated his eardrum—remaining damaged for the rest of his life. His grandmother resuscitated him by running her grandson under cold water until he gasped his first breath. Due to his injuries, his baptism at St. Francis Church in Hoboken was delayed until April 2, 1916. A childhood operation on his mastoid bone left major scarring on his neck, and during adolescence he was further scarred by cystic acne. Sinatra was raised in the Catholic Church.

Sinatra's mother was energetic and driven; biographers believe that she was the dominant factor in the development of her son's personality and self-confidence. Sinatra's fourth wife Barbara would later claim that Dolly was abusive to him when he was a child, and "knocked him around a lot". Dolly became influential in Hoboken and in local Democratic Party circles. She worked as a midwife, and according to Sinatra biographer Kitty Kelley, ran an illegal abortion service that catered to Italian Catholic girls, for which she was nicknamed "Hatpin Dolly". She also had a gift for languages and served as a local interpreter.

Sinatra's illiterate father was a bantamweight boxer who later worked at the Hoboken Fire Department, working his way up to captain. Sinatra spent much time at his parents' tavern in Hoboken, working on his homework and occasionally singing for spare change. During the Great Depression, Dolly provided money to her son for outings with friends and to buy expensive clothes, resulting in neighbors describing him as the "best-dressed kid in the neighborhood". Excessively thin and small as a child and young man, Sinatra's skinny frame later became a staple of jokes during stage shows.

At a young age, Sinatra developed an interest in music, particularly big band jazz and listened to Gene Austin, Rudy Vallée, Russ Colombo, and Bob Eberly while idolizing Bing Crosby. For his 15th birthday, his uncle Domenico gave him a ukulele, with which he performed at family gatherings. Sinatra attended David E. Rue Jr. High School from 1928, and A. J. Demarest High School (since renamed as Hoboken High School) in 1931, where he arranged bands for school dances, but left without graduating after having attended only 47 days before being expelled for "general rowdiness". To please his mother, he enrolled at Drake Business School, but departed after 11 months. Dolly found her son work as a delivery boy at the Jersey Observer newspaper, where his godfather Frank Garrick worked; he later worked as a riveter at the Tietjen and Lang shipyard. He began performing in local Hoboken social clubs, and sang for free on radio stations such as WAAT in Jersey City. In New York, Sinatra found jobs singing for his supper or for cigarettes. To improve his speech, he began taking elocution lessons for a dollar each from vocal coach John Quinlan, one of the first people to notice his impressive vocal range.

Music career

Hoboken Four, Harry James, and Tommy Dorsey (1935–1939)

Sinatra began singing professionally as a teenager. Even though he never learned to read music, he learned by ear. He got his first break in 1935 when his mother persuaded a local singing group called the 3 Flashes to let him join. Baritone Fred Tamburro stated that "Frank hung around us like we were gods or something", admitting that they only took him on board because he owned a car and could chauffeur the group around. Sinatra soon learned they were auditioning for the Major Bowes Amateur Hour show, and "begged" the group to let him in on the act.[48] With Sinatra, the group became known as the Hoboken Four, and passed an audition from Edward Bowes to appear on the show. They each earned $12.50, and ended up attracting 40,000 votes to win first prize—a six-month contract to perform on stage and radio across the U.S. Sinatra quickly became the group's lead singer, and, much to the jealousy of his fellow group members, garnered most of the attention from girls. Due to the success of the group, Bowes kept asking for them to return, disguised under different names, varying from "The Secaucus Cockamamies" to "The Bayonne Bacalas".

In 1938, Sinatra found employment as a singing waiter at a roadhouse called "The Rustic Cabin" in Englewood Cliffs, New Jersey, for which he was paid $15 a week. The roadhouse was connected to the WNEW radio station in New York City, and he began performing with a group live during the Dance Parade show. Despite the low salary, Sinatra felt that this was the break he was looking for, and boasted to friends that he was going to "become so big that no one could ever touch him". In March 1939, saxophone player Frank Mane, who knew Sinatra from Jersey City radio station WAAT, arranged for him to audition and record "Our Love", his first solo studio recording. In June, bandleader Harry James, who had heard Sinatra sing on "Dance Parade", signed a two-year contract of $75 a week after a show at the Paramount Theatre in New York. It was with the James band that Sinatra released his first commercial record "From the Bottom of My Heart" in July. No more than 8,000 copies of the record were sold, and further records released with James through 1939, such as "All or Nothing at All", also had weak sales on their initial release. Thanks to his vocal training, Sinatra could now sing two tones higher, and developed a repertoire which included songs such as "My Buddy", "Willow Weep for Me", "It's Funny to Everyone but Me", "Here Comes the Night", "On a Little Street in Singapore", "Ciribiribin", and "Every Day of My Life".

Sinatra and Tommy Dorsey in Ship Ahoy (1942)

Sinatra became increasingly frustrated with the status of the Harry James band, feeling that he was not achieving the major success and acclaim he was looking for. His pianist and close friend Hank Sanicola persuaded him to stay with the group, but in November 1939 he left James to replace Jack Leonard as the lead singer of the Tommy Dorsey band. Sinatra earned $125 a week, appearing at the Palmer House in Chicago, and James released Sinatra from his contract. On January 26, 1940, he made his first public appearance with the band at the Coronado Theatre in Rockford, Illinois, opening the show with "Stardust". Dorsey recalled: "You could almost feel the excitement coming up out of the crowds when the kid stood up to sing. Remember, he was no matinée idol. 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 was a major influence on Sinatra and became a father figure. Sinatra copied Dorsey's mannerisms and traits, becoming a demanding perfectionist like him, even adopting his hobby of toy trains. He asked Dorsey to be godfather to his daughter Nancy in June 1940. Sinatra later said that "The only two people I've ever been afraid of are my mother and Tommy Dorsey". Though Kelley says that Sinatra and drummer Buddy Rich were bitter rivals, other authors state that they were friends and even roommates when the band was on the road, but professional jealousy surfaced as both men wanted to be considered the star of Dorsey's band. Later, Sinatra helped Rich form his own band with a $25,000 loan and provided financial help to Rich during times of the drummer's serious illness.

In his first year with Dorsey, Sinatra recorded over forty songs. Sinatra's first vocal hit was the song "Polka Dots and Moonbeams" in late April 1940. Two more chart appearances followed with "Say It" and "Imagination", which was Sinatra's first top-10 hit. His fourth chart appearance was "I'll Never Smile Again", topping the charts for twelve weeks beginning in mid-July. Other records with Tommy Dorsey issued by RCA Victor include "Our Love Affair" and "Stardust" in 1940; "Oh! Look at Me Now", "Dolores", "Everything Happens to Me", and "This Love of Mine" in 1941; "Just as Though You Were There", "Take Me", and "There Are Such Things" in 1942; and "It Started All Over Again", "In the Blue of Evening", and "It's Always You" in 1943. As his success and popularity grew, Sinatra pushed Dorsey to allow him to record some solo songs. Dorsey eventually relented, and on January 19, 1942, Sinatra recorded "Night and Day", "The Night We Called It a Day", "The Song is You", and "Lamplighter's Serenade" at a Bluebird recording session, with Axel Stordahl as arranger and conductor. Sinatra first heard the recordings at the Hollywood Palladium and Hollywood Plaza and was astounded at how good he sounded. Stordahl recalled: "He just couldn't believe his ears. He was so excited; you almost believed he had never recorded before. I think this was a turning point in his career. I think he began to see what he might do on his own".

After the 1942 recordings, Sinatra believed he needed to go solo, with an insatiable desire to compete with Bing Crosby, but he was hampered by his contract which gave Dorsey 43% of Sinatra's lifetime earnings. A legal battle ensued, eventually settled in August 1942. On September 3, 1942, Dorsey bade farewell to Sinatra, reportedly saying "I hope you fall on your ass", but he was more gracious on the air when replacing Sinatra with singer Dick Haymes. Rumors began spreading in newspapers that Sinatra's mobster godfather, Willie Moretti, coerced Dorsey at gunpoint to let Sinatra out of his contract for a few thousand dollars. Sinatra persuaded Stordahl to come with him and become his personal arranger, offering him $650 a month, five times his salary from Dorsey. Dorsey and Sinatra, who had been very close, never reconciled their differences.

Onset of Sinatramania and role in World War II (1942–1945)

Perfectly simple: It was the war years and there was a great loneliness, and I was the boy in every corner drugstore, the boy who'd gone off drafted to the war. That's all.— Sinatra, on his popularity with young women

By May 1941, Sinatra topped the male singer polls in Billboard and DownBeat magazines. His appeal to bobby soxers, as teenage girls of that time were called, revealed a new audience for popular music, which had previously been recorded mainly for adults. The phenomenon became officially known as "Sinatramania" after his "legendary opening" at the Paramount Theatre in New York on December 30, 1942. According to Nancy Sinatra, Jack Benny later said, "I thought the goddamned building was going to cave in. I never heard such a commotion ... All this for a fellow I never heard of." Sinatra performed for four weeks at the theatre, his act following the Benny Goodman orchestra, after which his contract was renewed for another four weeks by Bob Weitman due to his popularity. He became known as "Swoonatra" or "The Voice", and his fans "Sinatratics". They organized meetings and sent masses of letters of adoration, and within a few weeks of the show, some 1000 Sinatra fan clubs had been reported across the US. Sinatra's publicist, George Evans, encouraged interviews and photographs with fans, and was the man responsible for depicting Sinatra as a vulnerable, shy, Italian–American with a rough childhood who made good. When Sinatra returned to the Paramount in October 1944 only 250 persons left the first show, and 35,000 fans left outside caused a near riot, known as the Columbus Day Riot, outside the venue because they were not allowed in. Such was the bobby-soxer devotion to Sinatra that they were known to write Sinatra's song titles on their clothing, bribe hotel maids for an opportunity to touch his bed, and steal clothing he was wearing, most commonly his bow-tie.

Sinatra signed with Columbia Records as a solo artist on June 1, 1943, during the 1942–44 musicians' strike. Columbia Records re-released Harry James and Sinatra's August 1939 version of "All or Nothing at All", which reached number 2 on June 2, and was on the best-selling list for 18 weeks. He initially had great success, and performed on the radio on Your Hit Parade from February 1943 until December 1944, and on stage. Columbia wanted new recordings of their growing star as quickly as possible, so Alec Wilder was hired as an arranger and conductor for several sessions with a vocal group called the Bobby Tucker Singers. Of the nine songs recorded during these sessions, seven charted on the best-selling list. That year he made his first solo nightclub appearance at New York's Riobamba, and a successful concert in the Wedgewood Room of the prestigious Waldorf-Astoria New York that year secured his popularity in New York high society. Sinatra released "You'll Never Know", "Close to You", "Sunday, Monday, or Always" and "People Will Say We're in Love" as singles. By the end of 1943 he was more popular in a DownBeat poll than Bing Crosby.

Sinatra did not serve in the military during World War II. On December 11, 1943, he was officially classified 4-F ("Registrant not acceptable for military service") by his draft board because of his perforated eardrum. However, Army files reported that Sinatra had actually been rejected because he was "not acceptable material from a psychiatric viewpoint;" his emotional instability was hidden to avoid "undue unpleasantness for both the selectee and the induction service". Briefly, there were rumors reported by columnist Walter Winchell that Sinatra paid $40,000 to avoid military service, but the FBI found this to be without merit.

Toward the end of the war, Sinatra entertained the troops during several successful overseas USO tours with comedian Phil Silvers. During one trip to Rome he met the Pope, who asked him if he was an operatic tenor. Sinatra worked frequently with the popular Andrews Sisters in radio in the 1940s, and many USO shows were broadcast to troops via the Armed Forces Radio Service (AFRS). In 1944 Sinatra released "I Couldn't Sleep a Wink Last Night" as a single and recorded his own version of Irving Berlin's "White Christmas". The following year he released "I Dream of You (More Than You Dream I Do)", "Saturday Night (Is the Loneliest Night of the Week)", "Dream", and "Nancy (with the Laughing Face)" as singles.[

Columbia years and career slump (1946–1952)

Despite being heavily involved in political activity in 1945 and 1946, in those two years Sinatra sang on 160 radio shows, recorded 36 times, and shot four films. 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 a week.

In 1946 Sinatra released "Oh! What it Seemed to Be", "Day by Day", "They Say It's Wonderful", "Five Minutes More", and "The Coffee Song" as singles, and launched his first album, The Voice of Frank Sinatra, which reached No. 1 on the Billboard chart. William Ruhlmann of AllMusic wrote that Sinatra "took the material very seriously, singing the love lyrics with utter seriousness", and that his "singing and the classically influenced settings gave the songs unusual depth of meaning". He was soon selling 10 million records a year. Such was Sinatra's command at Columbia that his love of conducting was indulged with the release of the set Frank Sinatra Conducts the Music of Alec Wilder, an offering unlikely to appeal to Sinatra's core fanbase of teenage girls at the time. The following year he released his second album, Songs by Sinatra, featuring songs of a similar mood and tempo such as Irving Berlin's "How Deep is the Ocean?" and Harold Arlen's and Jerome Kern's "All The Things You Are"."Mam'selle", composed by Edmund Goulding with lyrics by Mack Gordon for the film The Razor's Edge (1946), was released as a single. Sinatra had competition; versions by Art Lund, Dick Haymes, Dennis Day, and The Pied Pipers also reached the top ten of the Billboard charts. In December he recorded "Sweet Lorraine" with the Metronome All-Stars, featuring talented jazz musicians such as Coleman Hawkins, Harry Carney and Charlie Shavers, with Nat King Cole on piano, in what Charles L. Granata describes as "one of the highlights of Sinatra's Columbia epoch".

Sinatra's third album, Christmas Songs by Sinatra, was originally released in 1948 as a 78 rpm album set, and a 10" LP record was released two years later. When Sinatra was featured as a priest in The Miracle of the Bells, due to press negativity surrounding his alleged Mafia connections at the time, it was announced to the public that Sinatra would donate his $100,000 in wages from the film to the Catholic Church. By the end of 1948, Sinatra had slipped to fourth on DownBeat's annual poll of most popular singers, and in the following year he was pushed out of the top spots in polls for the first time since 1943. Frankly Sentimental (1949) was panned by DownBeat, who commented that "for all his talent, it seldom comes to life".

Sinatra in November 1950

Though "The Hucklebuck" reached the top ten, it was his last single release under the Columbia label. Sinatra's last two albums with Columbia, Dedicated to You and Sing and Dance with Frank Sinatra, were released in 1950. Sinatra would later feature a number of the Sing and Dance with Frank Sinatra album's songs, including "Lover", "It's Only a Paper Moon", "It All Depends on You", on his 1961 Capitol release, Sinatra's Swingin' Session!!!.

Cementing the low of his career was the death of publicist George Evans in January 1950. According to Jimmy Van Heusen, Sinatra's close friend and songwriter, Evans's death to him was "an enormous shock which defies words", as he had been crucial to his career and popularity with the bobbysoxers. Sinatra's reputation continued to decline as reports broke in February of his affair with Ava Gardner and the destruction of his marriage to Nancy, though he insisted that his marriage had long been over even before he met Gardner. In April, Sinatra was engaged to perform at the Copa club in New York, but had to cancel five days of the booking due to a submucosal hemorrhage of the throat. Evans once said that whenever Sinatra suffered from a bad throat and loss of voice it was always due to emotional tension which "absolutely destroyed him".

In financial difficulty following his divorce and career decline, Sinatra was forced to borrow $200,000 from Columbia to pay his back taxes after MCA refused to front the money. Rejected by Hollywood, he turned to Las Vegas and made his debut at the Desert Inn in September 1951, and also began singing at the Riverside Hotel in Reno, Nevada. Sinatra became one of Las Vegas's pioneer residency entertainers,  and a prominent figure on the Vegas scene throughout the 1950s and 1960s onwards, a period described by Rojek as the "high-water mark" of Sinatra's "hedonism and self-absorption". Rojek notes that the Rat Pack "provided an outlet for gregarious banter and wisecracks", but argues that it was Sinatra's vehicle, possessing an "unassailable command over the other performers". Sinatra would fly to Las Vegas from Los Angeles in Van Heusen's plane. On October 4, 1953, Sinatra made his first performance at the Sands Hotel and Casino, after an invitation by the manager Jack Entratter. Sinatra typically performed there three times a year, and later acquired a share in the hotel.

Sinatra's decline in popularity was evident at his concert appearances. At a brief run at the Paramount in New York he drew small audiences. At the Desert Inn in Las Vegas he performed to half-filled houses. At a concert at Chez Paree in Chicago, only 150 people turned up in a 1,200-seat venue. By April 1952 he was performing at the Kauai County Fair in Hawaii. Sinatra's relationship with Columbia Records was disintegrating, with A&R executive Mitch Miller claiming he "couldn't give away" the singer's records. Though several notable recordings were made during this time period, such as "If I Could Write a Book" in January 1952, which Granata sees as a "turning point", forecasting his later work with its sensitivity, Columbia and MCA dropped him later that year. His last studio recording for Columbia, "Why Try To Change Me Now", was recorded in New York on September 17, 1952, with orchestra arranged and conducted by Percy Faith. Journalist Burt Boyar observed, "Sinatra had had it. It was sad. From the top to the bottom in one horrible lesson."

Career revival and the Capitol years (1953–1962)

The release of the film From Here to Eternity in August 1953 marked the beginning of a remarkable career revival. Tom Santopietro notes that Sinatra began to bury himself in his work, with an "unparalleled frenetic schedule of recordings, movies and concerts", in what authors Anthony Summers and Robbyn Swan describe as "a new and brilliant phase". On March 13, 1953, Sinatra met with Capitol Records vice president Alan Livingston and signed a seven-year recording contract. His first session for Capitol took place at KHJ studios at Studio C, 5515 Melrose Avenue in Los Angeles, with Axel Stordahl conducting. The session produced four recordings, including "I'm Walking Behind You", Sinatra's first Capitol single. After spending two weeks on location in Hawaii filming From Here to Eternity, Sinatra returned to KHJ on April 30 for his first recording session with Nelson Riddle, an established arranger and conductor at Capitol who was Nat King Cole's musical director. After recording the first song, "I've Got the World on a String", Sinatra offered Riddle a rare expression of praise, "Beautiful!", and after listening to the playbacks, he could not hide his enthusiasm, exclaiming, "I'm back, baby, I'm back!"

In subsequent sessions in May and November 1953, Sinatra and Riddle developed and refined their musical collaboration, with Sinatra providing specific guidance on the arrangements. Sinatra's first album for Capitol, Songs for Young Lovers, was released on January 4, 1954, and included "A Foggy Day", "I Get a Kick Out of You", "My Funny Valentine", "Violets for Your Furs" and "They Can't Take That Away from Me", songs which became staples of his later concerts. That same month, Sinatra released the single "Young at Heart", which reached No. 2 and was awarded Song of the Year. In March, he recorded and released the single "Three Coins in the Fountain", a "powerful ballad" that reached No. 4. Sinatra's second album with Riddle, Swing Easy!, which reflected his "love for the jazz idiom" according to Granata, was released on August 2 of that year and included "Just One of Those Things", "Taking a Chance on Love", "Get Happy", and "All of Me". Swing Easy! was named Album of the Year by Billboard, and he was named "Favorite Male Vocalist" by Billboard, DownBeat, and Metronome that year. Sinatra came to consider Riddle "the greatest arranger in the world", and Riddle, who considered Sinatra "a perfectionist", offered equal praise of the singer, observing, "It's not only that his intuitions as to tempo, phrasing, and even configuration are amazingly right, but his taste is so impeccable ... there is still no one who can approach him."

In 1955 Sinatra released In the Wee Small Hours, his first 12" LP, featuring songs such as "In the Wee Small Hours of the Morning", "Mood Indigo", "Glad to Be Unhappy" and "When Your Lover Has Gone". According to Granata it was the first concept album of his to make a "single persuasive statement", with an extended program and "melancholy mood". Sinatra embarked on his first tour of Australia the same year. Another collaboration with Riddle resulted in Songs for Swingin' Lovers!, sometimes seen as one of his best albums, which was released in March 1956. It features a recording of "I've Got You Under My Skin" by Cole Porter, which reportedly took 22 takes to perfect.

His February 1956 recording sessions inaugurated the studios at the Capitol Records Building, complete with a 56-piece symphonic orchestra. According to Granata his recordings of "Night and Day", "Oh! Look at Me Now" and "From This Moment On" revealed "powerful sexual overtones, stunningly achieved through the mounting tension and release of Sinatra's best-teasing vocal lines", while his recording of "River, Stay 'Way from My Door" in April demonstrated his "brilliance as a syncopational improviser". Riddle said that Sinatra took "particular delight" in singing "The Lady is a Tramp", commenting that he "always sang that song with a certain amount of salaciousness", making "cue tricks" with the lyrics. His penchant for conducting was displayed again in 1956's Frank Sinatra Conducts Tone Poems of Color, an instrumental album that has been interpreted to be a catharsis to his failed relationship with Gardner. Also that year, Sinatra sang at the Democratic National Convention, and performed with The Dorsey Brothers for a week soon afterwards at the Paramount Theatre.

In 1957, Sinatra released Close to You, A Swingin' Affair! and Where Are You?—his first album in stereo, with Gordon Jenkins. Granata considers "Close to You" to have been thematically his closest concept album to perfection during the "golden" era, and Nelson Riddle's finest work, which was "extremely progressive" by the standards of the day. It is structured like a three-act play, each commencing with the songs "With Every Breath I Take", "Blame It on My Youth" and "It Could Happen to You". For Granata, Sinatra's A Swingin' Affair! and Songs for Swingin' Lovers! solidified "Sinatra's image as a 'swinger', from both a musical and visual standpoint". Buddy Collette considered the swing albums to have been heavily influenced by Sammy Davis Jr., and stated that when he worked with Sinatra in the mid-1960s he approached a song much differently than he had done in the early 1950s. On June 9, 1957, he performed in a 62-minute concert conducted by Riddle at the Seattle Civic Auditorium, his first appearance in Seattle since 1945. The recording was first released as a bootleg, but Artanis Entertainment Group officially released it as Sinatra '57 in Concert in 1999, after Sinatra's death. In 1958 Sinatra released the concept album Come Fly with Me with Billy May, designed as a musical world tour. It reached the top spot on the Billboard album chart in its second week, remaining at the top for five weeks, and was nominated for the Grammy Award for Album of the Year at the inaugural Grammy Awards. The title song, "Come Fly With Me", written especially for him, would become one of his best known standards. On May 29 he recorded seven songs in a single session, more than double the usual yield of a recording session, and an eighth, "Lush Life", was abandoned as Sinatra found it too technically demanding. In September, Sinatra released Frank Sinatra Sings for Only the Lonely, a stark collection of introspective saloon songs and blues-tinged ballads which proved a huge commercial success, spending 120 weeks on Billboard’s album chart and peaking at No. 1. Cuts from this LP, such as "Angel Eyes" and "One for My Baby (and One More for the Road)", would remain staples of the "saloon song" segments of Sinatra's concerts.

Pal Joey (1957)

In 1959, Sinatra released Come Dance with Me!, a highly successful, critically acclaimed album which stayed on Billboard's Pop album chart for 140 weeks, peaking at No. 2. It won the Grammy Award for Album of the Year, as well as Best Vocal Performance, Male and Best Arrangement for Billy May. He released No One Cares in the same year, a collection of "brooding, lonely" torch songs, which critic Stephen Thomas Erlewine thought was "nearly as good as its predecessor Where Are You?, but lacked the "lush" arrangements of it and the "grandiose melancholy" of Only the Lonely.

In the words of Kelley, by 1959, Sinatra was "not simply the leader of the Rat Pack" but had "assumed the position of il padrone in Hollywood". He was asked by 20th Century Fox to be the master of ceremonies at a luncheon attended by Soviet Premier Nikita Khrushchev on September 19, 1959. Nice 'n' Easy, a collection of ballads, topped the Billboard chart in October 1960 and remained in the charts for 86 weeks, winning critical plaudits.

Reprise years (1960–1981)

Sinatra grew discontented at Capitol, and fell into a feud with Alan Livingston, which lasted over six months. His first attempt at owning his own label was with his pursuit of buying declining jazz label Verve Records, which ended once an initial agreement with Verve founder Norman Granz "failed to materialize". He decided to form his own label, Reprise Records, and, in an effort to assert his new direction, temporarily parted with Riddle, May and Jenkins, working with other arrangers such as Neil Hefti, Don Costa, and Quincy Jones. Sinatra built the appeal of Reprise Records as one in which artists were promised creative control, as well as a guarantee that they would eventually gain "complete ownership of their work, including publishing rights." Under Sinatra the company developed into a music industry "powerhouse", and he later sold it for an estimated $80 million. His first album on the label, Ring-a-Ding-Ding! (1961), was a major success, peaking at No.4 on Billboard. The album was released in February 1961, the same month that Reprise Records released Ben Webster's The Warm Moods, Sammy Davis Jr.'s The Wham of Sam, Mavis River's Mavis and Joe E. Lewis's It is Now Post Time. During the initial years of Reprise, Sinatra was still under contract to record for Capitol, completing his contractual commitment with the release of Point of No Return, recorded on September 11 and 12, 1961.

In 1962, Sinatra released Sinatra and Strings, a set of standard ballads arranged by Don Costa, which became one of the most critically acclaimed works of Sinatra's Reprise period. Frank Jr., who was present during the recording, noted the "huge orchestra", which Nancy Sinatra stated "opened a whole new era" in pop music, with orchestras getting bigger, embracing a "lush string sound". Sinatra and Count Basie collaborated for the album Sinatra-Basie the same year, a popular and successful release which prompted them to rejoin two years later for the follow-up It Might as Well Be Swing, arranged by Quincy Jones. The two became frequent performers together, and appeared at the Newport Jazz Festival in 1965. Also in 1962, as the owner of his own record label, Sinatra was able to step on the podium as conductor again, releasing his third instrumental album Frank Sinatra Conducts Music from Pictures and Plays.

In 1963, Sinatra reunited with Nelson Riddle for The Concert Sinatra, an ambitious album featuring a 73-piece symphony orchestra arranged and conducted by Riddle. The concert was recorded on a motion picture scoring soundstage with the use of multiple synchronized recording machines that employed an optical signal onto 35 mm film designed for movie soundtracks. Granata considers the album to have been "impeachable", "one of the very best of the Sinatra-Riddle ballad albums", in which Sinatra displayed his vocal range, particularly in "Ol' Man River", in which he darkened the hue.

In 1964 the song "My Kind of Town" was nominated for the Academy Award for Best Original Song. Sinatra released Softly, as I Leave You, and collaborated with Bing Crosby and Fred Waring on America, I Hear You Singing, a collection of patriotic songs recorded as a tribute to the assassinated President John F. Kennedy. Sinatra increasingly became involved in charitable pursuits in this period. In 1961 and 1962 he went to Mexico to put on performances for Mexican charities, and in July 1964 he was present for the dedication of the Frank Sinatra International Youth Center for Arab and Jewish children in Nazareth.

Sinatra's phenomenal success in 1965, coinciding with his 50th birthday, prompted Billboard to proclaim that he may have reached the "peak of his eminence". In June 1965, Sinatra, Sammy Davis Jr., and Dean Martin played live in St. Louis to benefit Dismas House, a prisoner rehabilitation and training center with nationwide programs that in particular helped serve African Americans. The Rat Pack concert, called The Frank Sinatra Spectacular, was broadcast live via satellite to numerous movie theaters across America. The album September of My Years was released September 1965, and went on to win the Grammy Award for best album of the year. Granata considers the album to have been one of the finest of his Reprise years, "a reflective throwback to the concept records of the 1950s, and more than any of those collections, distills everything that Frank Sinatra had ever learned or experienced as a vocalist". One of the album's singles, "It Was a Very Good Year", won the Grammy Award for Best Vocal Performance, Male. A career anthology, A Man and His Music, followed in November, winning Album of the Year at the Grammys the following year.

In 1966 Sinatra released That's Life, with both the single of "That's Life" and album becoming Top Ten hits 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. 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. Sinatra was backed by the Count Basie Orchestra, with Quincy Jones conducting. Sinatra pulled out from the Sands the following year, when he was driven out by its new owner Howard Hughes, after a fight.

Sinatra started 1967 with a series of recording sessions with Antônio Carlos Jobim. He recorded one of his collaborations with Jobim, the Grammy-nominated album Francis Albert Sinatra & Antônio Carlos Jobim, which was one of the best-selling albums of the year, behind the Beatles's Sgt. Pepper's Lonely Hearts Club Band. According to Santopietro the album "consists of an extraordinarily effective blend of bossa nova and slightly swinging jazz vocals, and succeeds in creating an unbroken mood of romance and regret". Writer Stan Cornyn wrote that Sinatra sang so softly on the album that it was comparable to the time that he suffered from a vocal hemorrhage in 1950.

Sinatra released the album The World We Knew, which features a chart-topping duet of "Somethin' Stupid" with daughter Nancy. In December, Sinatra collaborated with Duke Ellington on the album Francis A. & Edward K. According to Granata, the recording of "Indian Summer" on the album was a favorite of Riddle's, noting the "contemplative mood [which] is heightened by a Johnny Hodges alto sax solo that will bring a tear to your eye". With Sinatra in mind, singer-songwriter Paul Anka wrote the song "My Way", using the melody of the French "Comme d'habitude" ("As Usual"), composed by Claude François and Jacques Revaux. Sinatra recorded it in one take, just after Christmas 1968. "My Way", Sinatra's best-known song on the Reprise label, was not an instant success, charting at No. 27 in the US and No. 5 in the UK, but it remained in the UK charts for 122 weeks, including 75 non-consecutive weeks in the Top 40, between April 1969 and September 1971, which was still a record in 2015. Sinatra told songwriter Ervin Drake in the 1970s that he "detested" singing the song, because he believed audiences would think it was a "self-aggrandizing tribute". According to NPR, "My Way" has become one the most requested songs at funerals.

In an effort to maintain his commercial viability in the late 1960s, Sinatra would record works by Paul Simon ("Mrs. Robinson"), the Beatles ("Yesterday"), and Joni Mitchell ("Both Sides, Now") in 1969.