Francis Albert Sinatra was born on December 12, 1915, in a tenement at 415 Monroe Street in Hoboken, New Jersey, the only child of Natalina "Dolly" Garaventa, who came from Genoa, and Antonino Martino "Marty" Sinatra, who came from Sicily and later rose to captain in the Hoboken Fire Department. He left high school without graduating, sang for spare change in his parents' tavern and for free on local radio, and never learned to read music well, working instead by ear. As a teenager he listened to big-band jazz and idolized Bing Crosby. In 1935 he joined a local vocal trio that went on the Major Bowes Amateur Hour as the Hoboken Four, won the contest, and toured on the prize contract.

His first real break came from the bands. In June 1939 bandleader Harry James signed him as vocalist at 75 dollars a week, and his first commercial record, "From the Bottom of My Heart," came out with the James band in July 1939, followed by "All or Nothing at All," recorded that August. He left James in November 1939 for the more successful orchestra of trombonist Tommy Dorsey, made his first appearance with it on January 26, 1940, in Rockford, Illinois, and recorded more than forty songs in his first year there. "I'll Never Smile Again" spent twelve weeks at the top of the charts beginning in mid-July 1940. He later credited Dorsey with a lesson that shaped his singing: Dorsey took quiet breaths at the side of his mouth while playing, and Sinatra trained his lungs, by swimming underwater among other methods, to carry a phrase through a whole stanza without a visible break. He recorded his first solo session on January 19, 1942, with the arranger Axel Stordahl, and left Dorsey that September after a legal dispute over the contract.

The solo years began with a frenzy. His opening at the Paramount Theatre in New York on December 30, 1942, set off a frenzy among teenage fans, the bobby soxers, that became known as "Sinatramania". He signed with Columbia as a solo artist on June 1, 1943, and his debut album, The Voice of Frank Sinatra (1946), reached No. 1 on the Billboard album chart. In December 1947 he sang "Sweet Lorraine" on a Metronome All-Stars date that included Coleman Hawkins, Harry Carney and Charlie Shavers, with Nat King Cole at the piano. By 1949 his popularity was falling, a throat hemorrhage interrupted a New York booking in 1950, and Columbia and his talent agency dropped him in 1952. His last Columbia studio session, on September 17, 1952, produced "Why Try to Change Me Now."

The turnaround came in 1953. He signed with Capitol Records on March 13, 1953, and on April 30 made his first record with the arranger Nelson Riddle, "I've Got the World on a String." His performance in From Here to Eternity (1953) won the Academy Award for Best Supporting Actor. The Capitol albums that followed are the core of his reputation: Songs for Young Lovers and Swing Easy! (both 1954), In the Wee Small Hours (April 25, 1955), a set of torch songs that helped establish the 12-inch LP in popular music, and Songs for Swingin' Lovers! (March 1956), arranged by Riddle and inducted into the Grammy Hall of Fame in 2000. Where Are You? (1957) was his first stereo album and the first with Gordon Jenkins instead of Riddle. Come Fly with Me (January 6, 1958), with Billy May, spent five weeks at No. 1, Only the Lonely (September 8, 1958) went back to Riddle's arrangements and the saloon-song mood, and Come Dance with Me! (January 5, 1959) won the Grammy for Album of the Year at the second Grammy Awards, with May winning Best Arrangement. In 1959 he toured Australia backed by the quintet of the vibraphonist Red Norvo, and tapes from the Melbourne shows were issued in 1997 as a live album.

In 1960 he left Capitol after a feud with its president, first tried to buy Norman Granz's Verve Records, then started his own label, Reprise. Its first record was Ring-a-Ding-Ding! (1961), arranged by Johnny Mandel, and its early artists included Duke Ellington. The jazz-band collaborations of the Reprise years came next. Sinatra-Basie: An Historic Musical First was recorded on October 2 and 3, 1962, in Hollywood with the Count Basie Orchestra and arrangements by Neal Hefti. It Might as Well Be Swing followed on June 9 to 12, 1964, his first studio record arranged by Quincy Jones, and the source of one of his best-known versions of "Fly Me to the Moon." The two men appeared together at the 1965 Newport Jazz Festival, and in January and February 1966 he recorded Sinatra at the Sands in the Copa Room of the Sands Hotel in Las Vegas, with the Basie band under Jones's direction. It was his first commercially released live album and was certified gold.

Two more jazz-world meetings followed. Francis Albert Sinatra & Antonio Carlos Jobim was recorded on January 30 and February 1, 1967, at United Western Recorders in Hollywood, with arrangements by Claus Ogerman and Jobim on guitar and piano; it was released in March 1967 and was nominated for Album of the Year at the 1968 Grammy Awards, losing to the Beatles' Sgt. Pepper's Lonely Hearts Club Band. A second set of Jobim sessions was shelved in 1969, and parts of it surfaced on Sinatra & Company (1971). In December 1967 he recorded Francis A. & Edward K. with Duke Ellington and his orchestra, with arrangements by Billy May. Dan Morgenstern gave it four stars in DownBeat and singled out "Indian Summer," with an alto solo by Johnny Hodges, as its masterpiece. "My Way," recorded just after Christmas 1968 and adapted from a French song, became one of his best-known songs.

He announced his retirement in June 1971 and returned in 1973 with Ol' Blue Eyes Is Back. In October 1974 he performed at Madison Square Garden with Woody Herman's Young Thundering Herd, and in 1975 he appeared in New York with Basie and Ella Fitzgerald and at the London Palladium with Basie and Sarah Vaughan. Trilogy: Past Present Future (1980) produced "Theme from New York, New York." In 1984 he made L.A. Is My Lady with Quincy Jones producing, his first studio album with Jones since 1964; it reached No. 8 on the Top Jazz Albums chart, and on its version of "Mack the Knife" he names Jones, Michael Brecker, Frank Foster and Lionel Hampton among the musicians he salutes. Duets (1993), on which contemporary stars added their voices to tracks he had recorded, became his best-selling album, and Duets II followed in 1994. His last public concerts were at the Fukuoka Dome in Japan on December 19 and 20, 1994. He passed away on May 14, 1998, at Cedars-Sinai Medical Center in Los Angeles after a heart attack, at the age of 82.

Away from the microphone his career had two very different halves. He worked as an actor for four decades: besides the Oscar for From Here to Eternity, he was nominated for Best Actor for The Man with the Golden Arm (1955), won a Golden Globe for Pal Joey (1957) and starred in The Manchurian Candidate (1962). He also spent decades answering questions about his associations. In 1951 investigators for the Kefauver Senate committee questioned him about photographs with figures from organized crime; he said he knew some of them and denied any business dealings. The FBI kept a file on him that ran to 2,403 pages. In 1963 the Nevada Gaming Control Board temporarily suspended his gambling license after the gangster Sam Giancana was seen at the Cal Neva Lodge, and he gave up his shares in that casino and the Sands. In 1981 his ten-day engagement at Sun City in the Bophuthatswana homeland drew criticism for breaking the cultural boycott of apartheid-era South Africa. He had a documented temper, particularly toward journalists, and was married four times. He also took public positions against racial segregation: he played a benefit at Carnegie Hall for Martin Luther King Jr. on January 27, 1961, and joined the push to desegregate Nevada's hotels and casinos in the 1950s and 1960s.

Sinatra was a pop standards singer, not a jazz improviser. He almost never scatted, he did not improvise on chord changes the way Ella Fitzgerald or Sarah Vaughan did, and a profile of Mel Tormé points out that Tormé, unlike Sinatra, would cut loose with scat choruses on up-tempo numbers. His jazz side is real but it is in the phrasing, the time and the company he kept. He started as a Bing Crosby admirer, took Tommy Dorsey's breath control as a model for long legato lines, and learned from Billie Holiday the importance of sounding as if he meant the words and from the cabaret singer Mabel Mercer the idea of a song as a short story. He told Ebony in 1958 that Holiday was the greatest single musical influence on him. A biographer of his recordings described his timing as letting him toy with the rhythm of a melody. The saxophonist Bob Berg recalled Miles Davis telling him to listen to the way Sinatra phrases, and Micky Weisman, a member of Sinatra's management team, recalled Davis saying he got a lot of his phrasing from Sinatra's records. The writer David Finck, in a 1995 article, called the Basie sessions among the favorite recordings of jazz musicians while noting that Sinatra himself probably would not have called himself a jazz musician.

The arrangers shaped the sound as much as the singer did. Nelson Riddle gave him the swinging brass-and-strings frame of the Capitol years, Billy May the punchier big-band setting of Come Fly with Me and Come Dance with Me!, Gordon Jenkins the string-heavy ballad albums, Johnny Mandel, Neal Hefti and Sy Oliver the Reprise swing dates, Don Costa the orchestral ones, and Claus Ogerman the bossa nova settings of the Jobim album. His own contribution was the insistence on recording live with the band in the room and on having direct input into the arrangements and tempos. Tony Bennett, whom Sinatra called the best singer in the business, said Sinatra had perfected the art of intimacy.

Whether he belongs in jazz is still argued. The case for it rests on his phrasing, his timing and his work with jazz musicians, and the case against rests on the near absence of improvisation and scat. The two subgenre tags above, Swing and Vocal Jazz, reflect the Capitol and Reprise swing albums and the three recordings with Basie, Ellington and Jobim, and leave out the pop, film and Las Vegas work that made up much of his career.