Early life

Francis Albert Sinatra was born on December 12, 1915, in an upstairs tenement at 415 Monroe Street in Hoboken, New Jersey, the only child of Italian immigrants Natalina “Dolly” Garaventa and Antonino Martino “Marty” Sinatra. 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—damage that remained for life. Due to his injuries at birth, 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 suffered from cystic acne that further scarred his face and neck. Sinatra was raised Roman Catholic.

Sinatra’s mother was energetic and driven, and biographers believe that she was the dominant factor in the development of her son’s personality traits and self-confidence. Sinatra’s fourth wife Barbara would later claim that Dolly was abusive to him as a child, and “knocked him around a lot”. Dolly became influential in Hoboken and in local Democratic Party circles. She worked as a midwife, earning $50 for each delivery, and according to Sinatra biographer Kitty Kelley, also 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 fought under the name Marty O’Brien. He later worked for 24 years 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 a song on top of the player piano 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.

Sinatra developed an interest in music, particularly big band jazz, at a young age. He listened to Gene Austin, Rudy Vallée, Russ Colombo, and Bob Eberly, and idolized Bing Crosby. Sinatra’s maternal uncle, Domenico, gave him a ukulele for his 15th birthday, and he began performing at family gatherings. Sinatra attended David E. Rue Jr. High School from 1928 and A. J. Demarest High School in 1931, where he arranged bands for school dances. He left without graduating, 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 Sinatra work as a delivery boy at the Jersey Observer newspaper, where his godfather Frank Garrick worked, and after that, Sinatra was a riveter at the Tietjen and Lang shipyard. He performed in local Hoboken social clubs such as The Cat’s Meow and The Comedy Club, 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, who was one of the first people to notice his impressive vocal range.

Music career

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 where both performed on live broadcasts, 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 one evening 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 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 signed a contract with Dorsey for $125 a week, appearing at the Palmer House in Chicago, and James agreed amicably to release 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 claims 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 in the entertainment industry. A legal battle ensued, eventually settled in August 1942. On September 3, 1942, Dorsey bade farewell to Sinatra, reportedly saying as Sinatra left, “I hope you fall on your ass”. He replaced Sinatra with singer Dick Haymes. Rumors began spreading in newspapers that Sinatra’s mobster godfather, Willie Moretti, coerced Dorsey to let Sinatra out of his contract for a few thousand dollars, holding a gun to his head. Sinatra persuaded Stordahl to leave Dorsey with him and become his personal arranger, offering him $650 a month, five times the salary of Dorsey. Dorsey and Sinatra, who had been very close, never patched up their differences before Dorsey’s death in 1956, worsened by the fact that Dorsey occasionally made biting comments to the press such as “he’s the most fascinating man in the world, but don’t put your hand in the cage”.

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 ten 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 at the time, which consisted of teenage girls. 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“.^[120] “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.^[122] 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 (behind Billy Eckstine, Frankie Laine, and Bing Crosby). 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”.

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 from a heart attack in January 1950 at 48. 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 out 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 had 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 suffering 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 single-engine plane. On October 4, 1953, Sinatra made his first performance at the Sands Hotel and Casino, after an invitation by the manager Jack Entratter, who had previously worked at the Copa in New York. 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 of wildcatters and ranchers. At a concert at Chez Paree in Chicago, only 150 people in a 1,200-seat capacity venue turned up to see him. By April 1952 he was performing at the Kauai County Fair in Hawaii. Sinatra’s relationship with Columbia Records was also 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.”

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 #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 #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 also 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 tempi, 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 the development of 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, something which Sinatra paid meticulous care to, taking a reported 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.

 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.^[196]

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 swing music predecessor 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 in 1999 Artanis Entertainment Group officially released it as the Sinatra ’57 in Concert live album, 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 was planned, “Lush Life“, but 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 Billboards 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.

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 #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 also 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 Billboardchart in October 1960 and remained in the charts for 86 weeks, winning critical plaudits. Granata noted the “lifelike ambient sound” quality of Nice and Easy, the perfection in the stereo balance, and the “bold, bright and snappy” sound of the band. He highlighted the “close, warm and sharp” feel of Sinatra’s voice, particularly on the songs “September in the Rain“, “I Concentrate on You“, and “My Blue Heaven“.

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 over their music, 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 over a two day period 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 entire Reprise period. Frank Sinatra 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” [sic], “one of the very best of the Sinatra-Riddle ballad albums”, in which Sinatra displayed an impressive 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, with the sole purpose of putting 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 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. 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 also 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 just after Christmas 1968. “My Way”, Sinatra’s best-known song on the Reprise label, was not an instant success, charting at #27 in the US and #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”, professing that he “hated boastfulness in others”.

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.

In 1970, Sinatra released Watertown, a critically acclaimed concept album, with music by Bob Gaudio (of the Four Seasons) and lyrics by Jake Holmes. However, it sold a mere 30,000 copies that year and reached a peak chart position of 101. He left Caesars Palace in September that year after an incident where executive Sanford Waterman pulled a gun on him. He performed several charity concerts with Count Basie at the Royal Festival Hall in London. On November 2, 1970, Sinatra recorded the last songs for Reprise Records before his self-imposed retirement, announced the following June at a concert in Hollywood to raise money for the Motion Picture and TV Relief Fund. He gave a “rousing” performance of “That’s Life”, and finished the concert with a Matt Dennis and Earl Brent song, “Angel Eyes” which he had recorded on the Only The Lonely album in 1958. He sang the last line.”‘Scuse me while I disappear.” The spotlight went dark and he left the stage. He told LIFE journalist Thomas Thompson that “I’ve got things to do, like the first thing is not to do anything at all for eight months … maybe a year”, while Barbara Sinatra later claimed that Sinatra had grown “tired of entertaining people, especially when all they really wanted were the same old tunes he had long ago become bored by”. While he was in retirement, President Richard Nixon asked him to perform at a Young Voters Rally in anticipation of the upcoming campaign. Sinatra obliged and chose to sing “My Kind of Town” for the rally held in Chicago on October 20, 1972.

In 1973, Sinatra came out of his short-lived retirement with a television special and album. The album, entitled Ol’ Blue Eyes Is Back, arranged by Gordon Jenkins and Don Costa, was a success, reaching number 13 on Billboard and number 12 in the UK.bThe television special, Magnavox Presents Frank Sinatra, reunited Sinatra with Gene Kelly. He initially developed problems with his vocal cords during the comeback due to a prolonged period without singing. That Christmas he performed at the Sahara Hotel in Las Vegas, and returned to Caesars Palace the following month in January 1974, despite previously vowing to perform there again [sic]. He began what Barbara Sinatra describes as a “massive comeback tour of the United States, Europe, the Far East and Australia”. In July, while on a second tour of Australia, he caused an uproar by describing journalists there – who were aggressively pursuing his every move and pushing for a press conference – as “bums, parasites, fags, and buck-and-a-half hookers”. After he was pressured to apologize, Sinatra instead insisted that the journalists apologize for “fifteen years of abuse I have taken from the world press”. Union actions cancelled concerts and grounded Sinatra’s plane, essentially trapping him in Australia. In the end, Sinatra’s lawyer, Mickey Rudin, arranged for Sinatra to issue a written conciliatory note and a final concert that was televised to the nation. In October 1974 he 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.

In 1975, Sinatra performed in concerts in New York with Count Basie and Ella Fitzgerald, and at the London Palladium with Basie and Sarah Vaughan, and in Tehran at Aryamehr Stadium, giving 140 performances in 105 days. In August he held several consecutive concerts at Lake Tahoe together with the newly-risen singer John Denver, who became a frequent collaborator. Sinatra had recorded Denver’s “Leaving on a Jet Plane” and “My Sweet Lady” for Sinatra & Company (1971), and according to Denver, his song “A Baby Just Like You” was written at Sinatra’s request for his new grandchild, Angela. During the Labor Day weekend held in 1976, Sinatra was responsible for reuniting old friends and comedy partners Dean Martin and Jerry Lewis for the first time in nearly twenty years, when they performed at the “Jerry Lewis MDA Telethon“. That year, the Friars Club selected him as the “Top Box Office Name of the Century”, and he was given the Scopus Award by the American Friends of the Hebrew University of Jerusalem in Israel and an honorary Doctor of Humane Letters from the University of Nevada.

Sinatra continued to perform at Caesars Palace in the late 1970s, and was performing there in January 1977 when his mother Dolly died in a plane crash on the way to see him. He cancelled two weeks of shows and spent time recovering from the shock in Barbados. In March, he performed in front of Princess Margaret at the Royal Albert Hall in London, raising money for the NSPCC. On March 14, he recorded with Nelson Riddle for the last time, recording the songs Linda, Sweet Loraine, and Barbara. The two men had a major falling out, and later patched up their differences in January 1985 at a dinner organized for Ronald Reagan, when Sinatra asked Riddle to make another album with him. Riddle was ill at the time, and died that October, before they had a chance to record.

In 1978, Sinatra filed a $1 million lawsuit against a land developer for using his name in the “Frank Sinatra Drive Center” in West Los Angeles. During a party at Caesars in 1979, he was awarded the Grammy Trustees Award, while celebrating 40 years in show business and his 64th birthday.  That year, former President Gerald Ford awarded Sinatra the International Man of the Year Award, and he performed in front of the Egyptian pyramids for Anwar Sadat, which raised more than $500,000 for Sadat’s wife‘s charities.

In 1980, Sinatra’s first album in six years was released, Trilogy: Past Present Future, a highly ambitious triple album that features an array of songs from both the pre-rock era and rock era. It was the first studio album of Sinatra’s to feature his touring pianist at the time, Vinnie Falcone, and was based on an idea by Sonny Burke. The album garnered six Grammy nominations – winning for best liner notes – and peaked at number 17 on Billboard’s album chart, and spawned yet another song that would become a signature tune, “Theme from New York, New York“. That year, as part of the Concert of the Americas, he performed in the Maracana Stadium in Rio de Janeiro, Brazil, which broke records for the “largest live paid audience ever recorded for a solo performer”. The following year, Sinatra built on the success of Trilogy with She Shot Me Down, an album that was praised for embodying the dark tone of his Capitol years. Also in 1981, Sinatra was embroiled in controversy when he worked a ten-day engagement for $2 million in Sun City, in the internationally unrecognized Bophuthatswana, breaking a cultural boycott against apartheid-era South Africa. President Lucas Mangope awarded Sinatra with the highest honor, the Order of the Leopard, and made him an honorary tribal chief.

Santopietro stated that by the early 1980s, Sinatra’s voice had “coarsened, losing much of its power and flexibility, but audiences didn’t care”. In 1982, he signed a $16 million three-year deal with the Golden Nugget of Las Vegas. Kelley notes that by this period Sinatra’s voice had grown “darker, tougher and loamier”, but he “continued to captivate audiences with his immutable magic”. She added that his baritone voice “sometimes cracked, but the gliding intonations still aroused the same raptures of delight as they had at the Paramount Theater”. That year he made a reported further $1.3 million from the Showtime television rights to his “Concert of the Americas” in the Dominican Republic, $1.6 million for a concert series at Carnegie Hall, and $250,000 in just one evening at the Chicago Fest. He donated a lot of his earnings to charity. He put on a performance at the White House for the Italian Prime Minister, and performed at the Radio City Music Hall with Luciano Pavarotti and George Shearing.

Sinatra was selected as one of the five recipients of the 1983 Kennedy Center Honors, alongside Katherine Dunham, James Stewart, Elia Kazan, and Virgil Thomson. Quoting Henry James, President Reagan said in honoring his old friend that “art was the shadow of humanity” and that Sinatra had “spent his life casting a magnificent and powerful shadow”. On September 21, 1983, Sinatra filed a $2 million court case against Kitty Kelley, suing her in punitive damages, before her unofficial biography, His Way, was even published. The book became a best-seller for “all the wrong reasons” and “the most eye-opening celebrity biography of our time”, according to William Safire of The New York Times. Sinatra was always adamant that such a book would be written on his terms, and he himself would “set the record straight” in details of his life. According to Kelley, the family detested her and the book, which took its toll on Sinatra’s health. Kelley claims that Tina Sinatra blamed her for her father’s colon surgery in 1986. He was forced to drop the case on September 19, 1984, with several leading newspapers expressing concerns about his views on censorship.

In 1984, Sinatra worked with Quincy Jones for the first time in nearly two decades on the album, L.A. Is My Lady, which was well received critically. The album was a substitute for another Jones project, an album of duets with Lena Horne, which had to be abandoned. In 1986, Sinatra collapsed on stage while performing in Atlantic City and was hospitalized for diverticulitis, which left him looking frail. Two years later, Sinatra reunited with Martin and Davis, Jr. and went on the Rat Pack Reunion Tour, during which they played a number of large arenas. When Martin dropped out of the tour early on, a rift developed between them and the two never spoke again.

On June 6, 1988, Sinatra made his last recordings with Reprise for an album which was not released. He recorded “My Foolish Heart“, “Cry Me A River“, and other songs. Sinatra never completed the project, but take number 18 of “My Foolish Heart” may be heard in The Complete Reprise Studio Recordings (1995).

In 1990, Sinatra was awarded the second “Ella Award” by the Los Angeles-based Society of Singers, and performed for a final time with Ella Fitzgerald at the award ceremony. Sinatra maintained an active touring schedule in the early 1990s, performing 65 concerts in 1990, 73 in 1991 and 84 in 1992 in seventeen different countries.

In 1993, Sinatra returned to Capitol Records and the recording studio for Duets, which became his best-selling album. The album and its sequel, Duets II, released the following year, would see Sinatra remake his classic recordings with popular contemporary performers, who added their vocals to a pre-recorded tape. During his tours in the early 1990s, his memory failed him at times during concerts, and he fainted onstage in Richmond, Virginia, in March 1994. His final public concerts were held in Fukuoka Dome in Japan on December 19–20, 1994. The following year, Sinatra sang for the very last time on February 25, 1995, before a live audience of 1200 select guests at the Palm Desert Marriott Ballroom, on the closing night of the Frank Sinatra Desert Classic golf tournament. Esquire reported of the show that Sinatra was “clear, tough, on the money” and “in absolute control”. Sinatra was awarded the Legend Award at the 1994 Grammy Awards, where he was introduced by Bono, who said of him, “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?”

In 1995, to mark Sinatra’s 80th birthday, the Empire State Building glowed blue.^[342] A star-studded birthday tribute, Sinatra: 80 Years My Way, was held at the Shrine Auditorium in Los Angeles, featuring performers such as Ray Charles, Little Richard, Natalie Cole and Salt-N-Pepa singing his songs. At the end of the program Sinatra graced the stage for the last time to sing the final notes of the “Theme from New York, New York” with an ensemble. In recognition of his many years of association with Las Vegas, Frank Sinatra was elected to the Gaming Hall of Fame in 1997.