Baritone Frank Sinatra was indisputably the 20th century's greatest singer of popular song. Though influenced by Bing Crosby's crooning, and by learning from trombonist Tommy Dorsey's breath control and blues singer Billie Holiday's rhythmic swing, Frank Sinatra mainstreamed the concept of singing colloquially, treating lyrics as personal statements and handling melodies with the ease of a jazz improviser. His best work is standards —Cole Porter, Irving Berlin, Jerome Kern, and the Gershwins —but Sinatra, despite his 1957 denunciation of rock & roll as degenerate, has recorded songs by the likes of Stevie Wonder, George Harrison, Jimmy Webb, and Billy Joel. Not only did his freely interpretive approach pave the way for the idiosyncrasies of rock singing, but with his character a mix of tough-guy cool and romantic vulnerability, he became the first true pop idol, a superstar who through his music established a persona audiences found compelling and true.
Sinatra, an only child of a family with Sicilian roots, grew up in Hoboken, and sang in the glee club of Demarest High School. His break came in 1937, when he and three instrumentalists, billed as the Hoboken Four, won on the Major Bowes Original Amateur Hour. After some touring, the group disbanded.Harry James signed Sinatra to sing with his orchestra, and on July 13, 1939, two weeks after his debut as a big-band vocalist at the Hippodrome Theatre in Baltimore, Sinatra cut his first disc, "From the Bottom of My Heart," with the orchestra. Of the 10 sides he recorded with them, the biggest seller, "All or Nothing at All," sold just over 8,000 copies upon release. In 1943 it was rereleased and became the first of Sinatra's many million-sellers, hitting #2 on the chart.
In 1940 Tommy Dorsey's lead singer, Jack Leonard, quit and Sinatra began a two-year stay with the trombonist. During those years, the band consistently hit the Top 10 (15 entries in 1940–41, including their first, the #1 hit "I'll Never Smile Again"). His radio work with Dorsey was the springboard for Sinatra's solo career. During the war years, Sinatra, married at the time to his childhood sweetheart, Nancy, sang love songs to his mostly female audiences, notably on Lucky Strike's Hit Parade and at New York's original Paramount Theatre. Between 1943 and 1946 he had 17 Top 10 chart singles, and earned the sobriquets "The Voice" and "The Sultan of Swoon." With the GIs back in the U.S., public taste shifted away from these songs, and Sinatra's popularity waned. At Columbia, producer Mitch Miller burdened Sinatra with novelty songs (washboard accompaniment on one, barking dogs on another), and his sales slipped to an average of 30,000 per record. In the early '50s, he was dropped by Columbia and by his talent agent and lost his MGM motion picture contract. To regain his popularity, he begged to be cast as Maggio in the film From Here to Eternity. His first nonsinging role, it won him a 1953 Oscar and a return to the limelight. (His film debut had been with the Tommy Dorsey Orchestra in 1941's Las Vegas Nights.)
The fledgling Capitol Records signed him in 1953 and, with ex-Dorsey trombonist and arranger Nelson Riddle, Sinatra moved into the next phase of his recording career with a new emphasis: saloon ballads and sophisticated swing tunes. With Capitol, he concentrated on albums, although he again charted in the singles Top 10, notably with "Young at Heart" (#2, 1954), "Learnin' the Blues" (#1, 1955), "Hey! Jealous Lover" (#3, 1956), "All the Way" (#2, 1957), and "Witchcraft" (#6, 1958). His best albums of the period were arranged by Riddle, Billy May, or Gordon Jenkins.
Through the early '50s, during which he was married to film actress Ava Gardner, having left Nancy in 1950, Sinatra became a movie star. He won especially high praise for his portrayal of a drug addict in The Man With the Golden Arm (1955). Beginning in 1959, two years after he divorced Gardner, his singles failed to hit the Top 30, and in 1961 Sinatra left Capitol to establish his own company, Reprise. (In 1963 he sold Reprise to Warner Bros. and became a vice president and consultant of Warner Bros. Picture Corp.)
Sinatra decided to try again to become a Top 40 singles artist. "The Second Time Around" hit #50 in 1961; subsequent releases charted lower. But in the mid-'60s he recouped. He was the triumphant headliner of the final evening of the 1965 Newport Jazz Festival in a 20-song set accompanied by Count Basie's orchestra, conducted by Quincy Jones. His 1965 Thanksgiving TV special, Frank Sinatra: A Man and His Music, a review of his 25-year career, won an Emmy and set the precedent for numerous other TV specials, including one each in the next four years. That year he also picked up a Grammy Lifetime Achievement Award. In 1966–67 he charted three of his biggest Top 10 hits: "Strangers in the Night" (#1, 1966), "That's Life" (#4, 1966), and a duet with daughter Nancy, "Somethin' Stupid" (#1, 1967).
In the 1960s he made his Las Vegas debut at the Sands and continued for years as a main attraction at Caesars Palace. Leader of the notorious "Rat Pack," including Sammy Davis Jr., Dean Martin, Peter Lawford, and Joey Bishop, he came to epitomize the hard-drinking, blonde-chasing swinger; a stout Democrat who'd named his son after Franklin D. Roosevelt, he also strongly supported John F. Kennedy's presidential bid. Married from 1966 to 1968 to actress Mia Farrow, he began reconciling with youth culture, covering songs, with indifferent success, by younger writers. In 1968 he recorded "My Way," a French song to which Paul Anka wrote new English lyrics. A modest U.S. hit (#27), it was an overwhelming smash in the U.K., staying in the Top 50 an unprecedented 122 weeks. (Sex Pistol Sid Vicious later recorded a sarcastic version.)
In 1970 Sinatra announced his retirement and was honored with a gala farewell on June 13, 1971, at the L.A. Music Center. He reversed that decision in 1973 with the release of Ol' Blue Eyes Is Back (#13), a TV special of the same name, and a performance at the Nixon White House (over the years, Sinatra's politics had become markedly conservative; in 1985, he would produce Ronald Reagan's inaugural gala). In 1974 he mounted an eight-city, 13-date sold-out U.S. tour and performed in Japan and Australia. In Australia he aggravated the paparazzi with his antijournalist harangues: Through the years he referred to the males as parasites, and the females as everything from "a buck-and-a-half hooker" to "two-dollar broads." Married to Zeppo Marx's widow, Barbara, in 1976, however, he appeared to mellow somewhat. In the mid-'70s Sinatra's career slowed down, but in mid-1980, after a five-year recording hiatus, he released Trilogy (#17),which included a version of "Theme From New York, New York" (#32) that the city fervently adopted.
In the 1980s Sinatra continued to perform sold-out concerts in major halls, to star in movies and TV specials, and to spark controversy for his business and political associations. (His 1972 appearances before the House Select Committee on Crime investigating criminal infiltration into horse racing were front-page news.) With 1981's She Shot Me Down (#52) and 1984's L.A. Is My Lady (#58) he appeared to have ended his recording career. In 1985, he was accorded the Presidential Medal of Freedom, the nation's highest civilian award.
In 1993, however, he enjoyed a renaissance with Duets debuting at #2. Featuring top singers —among them Aretha Franklin, Bono, Tony Bennett, Liza Minnelli, and Luther Vandross (some recording their parts via telephone) —it gained Sinatra new young fans. Still touring, with the aid of TelePrompTers, at 78, he collapsed onstage in Virginia in 1994 but soon recovered; days earlier, when presented with a special "Legend" award at the Grammy Awards ceremony —with an over-the-top intro by Bono —he had waxed so emotional that his own handlers requested that television cameras cut away from his acceptance speech. Rumors abounded about Sinatra's health, but he insisted on resuming his tour. By year's end, the sequel Duets II was issued, featuring Chrissie Hynde, Linda Ronstadt, and Willie Nelson, among others.
A 1983 honoree at the Kennedy Center Honors, Sinatra was involved for many years in charitable work, particularly in fundraising for multiple sclerosis, chronically ill children, and awareness of child abuse.
Frank Sinatra died of a heart attack on May 14, 1998, in L.A. That year, his FBI dossier, 1,275 pages covering 50 years of surveillance, was released. The document revealed no shocking secrets.
This biography originally appeared in The Rolling Stone Encyclopedia of Rock & Roll (Simon & Schuster, 2001).